Fused quinone oxime imidazoles and onium derivatives thereof, and preparation and use thereof

Abstract

The application discloses a fused quinone oxime imidazole and onium derivative thereof, and preparation and application thereof. The structure is represented by general formula (I), (II), (III) and (IV) as follows: the structure is novel, and the substituted quinone imidazole and onium derivative thereof are fused with aromatic carbocyclic or heterocyclic rings and characterized by oxime substitution. In-vivo and in-vitro tests of the derivative show good tumor cell growth inhibition activity, and excellent selectivity, and have good anti-tumor application prospect. In addition, the derivative also has good antiviral and antibacterial effects.

Description

Technical Field

[0001] This invention belongs to the pharmaceutical field and relates to a fused quinone oxime-imidazolium and its onium derivatives, their preparation and uses; particularly to a class of quinone oxime-imidazolium onium derivatives useful for treating cancer and for antibacterial and antiviral purposes, their preparation, and their new synthetic intermediates and their preparation. Background Technology

[0002] Quinone-containing compounds are widely found in nature, many of which possess excellent biological activities. For example, doxorubicin and mitomycin C are used clinically as chemotherapy drugs to treat various cancers, while shikonin and its derivatives exhibit a variety of biological activities, including anti-inflammatory, anticancer, antiviral, antithrombotic, hypoglycemic, and hepatoprotective effects. Synthetic quinone-containing drugs also have a wide range of applications; doxorubicin and epirubicin are both excellent first-line anticancer drugs. In recent years, research on the anticancer activity of quinone-containing active substances has attracted considerable attention. Nitrogen-containing heterocyclic carbenes are a class of highly active and widely used organometallic catalyst ligands and small molecule catalysts, characterized by high efficiency, availability, ease of modification, and low cost. These characteristics highly overlap with those of drug molecules.

[0003] Existing literature reports two main types of structural modifications to quinone imidazole derivatives: one is the sporadic, unsystematic development of monosubstituted imidazole products (US Patent, US 20090163545 A1 20090625; International Patents, WO 2009023773 A2 20090219, WO 2012149523 A1 20121101); the other is the synthesis of 2-substituted naphthoquinone imidazole noncarbene precursor derivatives by introducing a fixed group at the 2-position of the imidazole and then modifying the imidazole structure (Japanese Patent, JP 2014156400 A 20140829; US Patent, US 20150086535 A1 20150326; International Patents, 2001060803A1 20010823, 2004092160A1). (References: 20041028, 2012161177A1, 20121129, 2013148649A1, 20131003, 2014142220A1, 20140918). This invention utilizes interdisciplinary thinking to organically combine quinone compounds with carbenes and oximeize them, thus designing and synthesizing for the first time a series of quinone oxime imidazole derivatives with highly efficient anticancer activity. Summary of the Invention

[0004] Currently, chemotherapy is the primary treatment for cancer. However, the toxicity of chemotherapy drugs used clinically cannot be ignored. Therefore, the development of highly active, low-toxicity, safe, and reliable anticancer drugs is urgently needed. This invention, through in-depth research on quinone drugs, has discovered that the toxicity of quinone compounds mainly comes from the ROS produced during the conversion of quinones to quinone oximes. Furthermore, the natural quinone oxime product, shikonin, possesses excellent anticancer activity. Therefore, the purpose of this invention is to provide a class of fused quinone oxime imidazoles and their onium derivatives, along with their preparation and uses. These compounds have novel structures, are easy to prepare, and exhibit good antitumor activity in in vivo and in vitro experiments, with low toxicity and high safety.

[0005] The objective of this invention is achieved through the following technical solution:

[0006] In a first aspect, the present invention relates to a fused quinone oxime-imidazolium derivative having the following general formulas (I) and (II);

[0007] Its structural formula is as follows:

[0008] The symbols in the formula have the following meanings:

[0009] A ring: selected from aromatic rings with or without one or more substituents, or heteroaromatic rings with or without one or more substituents;

[0010] R 1 R 2 R 3 and R 4 : Same or different, each representing - hydrogen atom, - lower chain alkyl with or without one or more substituents, - lower chain alkenyl with or without one or more substituents, - lower alkynyl with or without one or more substituents, - saturated heterocyclic with or without one or more substituents, - cycloalkyl with or without one or more substituents, - cycloalkenyl with or without one or more substituents, - aryl with or without one or more substituents, - heteroaryl with or without one or more substituents;

[0011] The above A ring and R 1 R 2 R 3 and R 4 The substituents can be selected from groups of group B;

[0012] Group B: - Lower alkyl groups with no or one or more substituents, - Lower alkenyl groups with no or one or more substituents, - Lower alkynyl groups with no or one or more substituents, - Saturated heterocyclic groups with no or one or more substituents, - Cycloalkyl groups with no or one or more substituents, - Cycloalkenyl groups with no or one or more substituents, - Aryl groups with no or one or more substituents, - Heteroaryl groups with no or one or more substituents, -OR a -SR a-O-lower alkylene-OR a -O-lower alkylene-O-lower alkylene-OR a -O-lower alkylene-O-lower alkylene-O-lower alkylene-OR a -O-lower alkylene-NR a R b -O-lower alkylene-O-lower alkylene-NR a R b -O-lower alkylene-NR c -lower alkylene-NR a R b -O-CO-NR a R b -SOR a -SO2R a -SO2NR a R b -NR a -SO2R b -NR a R b -NR c -lower alkylene-NR a R b -N(-lower alkylene-NR) a R b 2, -NO2, -CN, -halogen, -CO2R a -COO - -CONR a R b -CONR a -OR b -NR a -COR b -NR a -CO-NR b R c -OCOR a and -COR a ;

[0013] R a R b and R c: Same or different, each representing - hydrogen atom, - lower chain alkyl with or without one or more substituents, - lower chain alkenyl with or without one or more substituents, - lower alkynyl with or without one or more substituents, - saturated heterocyclic group with or without one or more substituents, - cycloalkyl with or without one or more substituents, - cycloalkenyl with or without one or more substituents, - aryl with or without one or more substituents, - heteroaryl with or without one or more substituents, - lower alkylene- (5- to 7-membered saturated heterocycle with or without one or more substituents), - lower alkylene- (cycloalkyl with or without one or more substituents), - lower alkylene- (aryl with or without one or more substituents), - lower alkylene- (heteroaryl with or without one or more substituents); wherein, substituent refers to lower alkyl or heteroalkyl;

[0014] X - Counter anions include halide ions, sulfonate ions (methanesulfonate, trifluoromethanesulfonate, benzenesulfonate, p-toluenesulfonate, etc.), acetate ions, trifluoroacetate ions, carbonate ions, sulfate ions, etc.; when the anion on the substituent forms an inner salt with the imidazolium cation, X - It does not exist.

[0015] As one embodiment of the present invention, in the structural formula,

[0016] Ring A: Selected from an aromatic ring with no or one or more substituents; the substituent is NO2;

[0017] R 1 : Selected from -hydrogen atom, -lower chain alkyl with one or more substituents, -lower chain alkenyl with one or more substituents, -lower chain alkynyl with one or more substituents, -aryl with one or more substituents;

[0018] The substituent is selected from -cycloalkyl, -aryl, -OR a -O-lower chain alkyl-OR a -O-lower chain alkyl-O-lower chain alkyl-OR a -OR a Substituted aryl, -halogen-substituted aryl, -CF3-substituted aryl, -NO2-substituted aryl, -NH2; wherein, R a It is a lower chain alkyl group substituted with a hydrogen atom, an aryl group, a lower chain alkyl group, or an aryl-substituted lower chain alkyl group;

[0019] R 2 : Selected from lower chain alkyl groups with no or one or more substituents;

[0020] R 3Selected from -hydrogen atom, -lower chain alkyl with no or one or more substituents, -cycloalkyl, -aryl, -heterocyclic, -lower chain alkyl-substituted aryl, -OR a And / or halogen-substituted aryl, -heteroaryl, -lower chain alkyl-substituted heteroaryl;

[0021] The substituent is a heteroaryl, a halogen, or a lower chain alkyl-substituted heteroaryl; R a - Lower chain alkyl;

[0022] R 4 : Selected from -hydrogen atom, -lower chain alkyl with no or one or more substituents, -lower chain alkenyl with no or one or more substituents, -lower chain alkynyl with no or one or more substituents, -cycloalkyl, -aryl with no or one or more substituents;

[0023] The substituent is -CN, lower chain alkyl, halogen, OR. a Substituted aryl, OR a heteroaryl, aryl, halogen-substituted aryl, -CO2R a , saturated heterocyclic groups, -O-lower chain alkyl-OR a ;R a It is a lower-chain alkyl group.

[0024] As another embodiment of the present invention, in the structural formula,

[0025] Ring A: Selected from benzene rings, naphthalene rings, or NO2-substituted benzene rings;

[0026] R 1 Selected from -hydrogen atom, -lower alkyl, -lower alkynyl, -lower alkenyl, -lower chain alkyl-O-lower chain alkyl, -lower chain alkyl-O-aryl, -lower chain alkyl-O-lower chain alkyl-O-lower chain alkyl, -lower chain alkyl-O-lower chain alkyl-O-lower chain alkyl-O-lower chain alkyl, -aryl, -5 to 7-membered saturated heterocycles, -heteroaryl;

[0027] R 2 Selected from lower chain alkyl groups;

[0028] R 3 Selected from -hydrogen atom, -lower chain alkyl, -3 to 7-membered saturated cycloalkyl, -heterocyclic, -aryl, -lower chain alkyl-substituted aryl, -halogen-substituted aryl, -heteroaryl, -lower chain alkyl-substituted heteroaryl, -O-lower chain alkyl, -S-lower chain alkyl, -acyl, -lower chain alkyl-substituted acyl;

[0029] R 4Selected from -hydrogen atom, -lower chain alkyl, -lower chain alkenyl, -lower chain alkynyl, -aryl, -CN, -3 to 7-membered saturated cycloalkyl, -halogen-substituted aryl, -lower alkyl-substituted aryl, -heteroaryl, -CO2R a -Saturated heterocyclic group, -lower chain alkyl-OR a -lower chain alkyl-O-lower chain alkyl, -lower chain alkyl-S-lower chain alkyl, -lower chain alkyl-O-lower chain alkyl-OR a ;R a It is a lower-chain alkyl group.

[0030] As another embodiment of the present invention, in the structural formula,

[0031] Ring A: Selected from benzene rings, naphthalene rings, or NO2-substituted benzene rings;

[0032] R 1 Selected from -hydrogen atom, -C1 to C6 straight-chain alkyl or branched-chain alkyl, -benzyl, -C4 to C6 methylcycloalkyl, -C3 to C6 alkenyl, -CH2(C6H 5-m -X m (m = 1 to 5, X is a halogen atom, NO2, hydrogen atom or -OC) n H 2n+1，n＝1～6 -CH2(C6H4-CH) n X 3-n (n = 1 to 3, X is a halogen atom), -(C n H 2n -O) y -C m H 2m+1 (n=1~6, m=1~6, y=1~3), -C n H 2n -OC m H 2m -Ph(n=1~6, m=1~6), -C n H 2n -NH2 (n=1~6) or -CH2CH (-OCH2CH2O-);

[0033] R 2 Selected from lower chain alkyl groups;

[0034] R 3 Selected from -hydrogen atom, -C1 to C6 straight-chain alkyl or branched alkyl, -C4 to C6 methylcycloalkyl, -heteroaryl, -phenyl or substituted phenyl;

[0035] R 4Selected from -C1 to C6 straight-chain alkyl or branched-chain alkyl, -C3 to C6 methylcycloalkyl, -lower alkylene-O-lower alkyl, -C3 to C6 alkenyl, -benzyl or substituted benzyl, -ester or substituted ester, -phenyl or substituted phenyl, -CH2(thienyl) or -CH2CH(-OCH2CH2O-).

[0036] As another embodiment of the present invention, in the structural formula,

[0037] Ring A: Selected from benzene rings, naphthalene rings, or NO2-substituted benzene rings;

[0038] R 1 Selected from -hydrogen atom, -C1 to C6 straight-chain alkyl or branched-chain alkyl, -benzyl, -C4 to C6 methylcycloalkyl, -C3 to C6 alkenyl, -CH2(C6H 5-m -X m (m = 1 to 5, X is a halogen atom, NO2, hydrogen atom or -OC) n H 2n+1 (n=1~6), -CH2(C6H4-CH n X 3-n (n = 1 to 3, X is a halogen atom), -(C n H 2n -O) y -C m H 2m+1 (n=1~6, m=1~6, y=1~3), -C n H 2n -OC m H 2m -Ph(n=1~6, m=1~6), -C n H 2n -NH2 (n=1~6) or -CH2CH (-OCH2CH2O-);

[0039] R 2 Selected from lower chain alkyl groups;

[0040] R 3 Selected from -hydrogen atom, -methyl, -phenyl or substituted phenyl;

[0041] R 4 Selected from straight-chain alkyl or branched-chain alkyl groups from -C1 to C6;

[0042] X: Selected from Br, I, OMs, OTs.

[0043] As another embodiment of the present invention, the derivative includes,

[0044] (E)- or (Z)-4-(hydroxyimino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-onthium, (E)- or (Z)-1-ethyl-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-onthium, (E)- or (Z)-1-propyl-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-onthium, (E)- or (Z)-1-propyl-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-onthium, (E)- or (Z)-1-butyl-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol- 3-Onium, (E)- or (Z)-1-isopropyl-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-onium, (E)- or (Z)-1-isobutyl-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-onium, (E)- or (Z)-1-(2-methylbutyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-onium, (E)- or (Z)-1-tert-butyl ... H-Naphtho[2,3-d]imidazol-3-onthium, (E)- or (Z)-1-cyclopropyl-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-onthium, (E)- or (Z)-1-(2-methoxyethyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-onthium, (E)- or (Z)-1-(3-methyl-2-en-1-yl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-onthium, (E)- or (Z)-1-benzyl-4- (hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-onyl, (E)- or (Z)-1-(2-ethoxy-2-oxoethyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-onyl, (E)- or (Z)-1-phenyl-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-onyl, (E)- or (Z)-1-(2,4,6-trimethylphenyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-onyl, (E)- or (Z)-1-(2,4,6-trimethylphenyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-onyl, (E)- or (Z)-1-(2,4,6-trimethylphenyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-onyl,[3-d]imidazol-3-onium, (E)- or (Z)-1-(thiophene-2-methyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-onium, (E)- or (Z)-1-((1,3-dioxane-2-yl)methyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-onium, (E)- or (Z)-1-(4-fluorobenzyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-onium, (E)- or (Z)-1-(2-fluorophenyl)-4-(hydroxyimino) )-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-onthium, (E)- or (Z)-1-(3-fluorophenyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-onthium, (E)- or (Z)-1-(4-fluorophenyl)- 4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-onthium, (E)- or (Z)-1-(2-fluorobenzyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-onthium, (E)- or (Z)-1-( 3-Fluorobenzyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-onyl, (E)- or (Z)-1-(4-methoxyphenyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-onyl, (E)- or (Z)-1-(4-methoxyphenyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-onyl, (E)- or (Z)-1-(3-chloro-4-fluorophenyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-onyl, (E)- or (Z)-1-(3-chloro-4-fluorophenyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-onyl, (E)- or (Z)-1-1-(3-chloro-4-fluorophenyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-onyl, (E)- or (Z)-1-1-(3-chloro-4-fluorophenyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-onyl, [3-d]imidazol-3-onium, (E)- or (Z)-1-(3-bromo-4-fluorophenyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-onium, (E)- or (Z)-1-butyl-4-(methoxyimino)-3-methyl-9-oxo-4,9-dihydro-1H -Naphtho[2,3-d]imidazolium, (E)- or (Z)-1-butyl-4-(ethoxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazolium, (E)- or (Z)-1-butyl-4-(benzyl ...[3-d]imidazolium, (E)- or (Z)-1-butyl-4-(methoxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazolium, (E)- or (Z)-1-butyl-4-(methoxyimino)-3-ethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazolium Ononium, (E)- or (Z)-4-(methoxyimino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazolium, (E)- or (Z)-4-(ethoxyimino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazolium, (E)- or (Z)- -4-(benzyloxyimino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazolium, (E)- or (Z)-3-ethyl-4-(methoxyimino)-1-methyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazolium, (E)- or (Z)-4-(isopropoxyimino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazolium, (E)- or (Z)-4-(butoxyimino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazolium, (E)- or (Z)-4-(isobutoxyimino)-1,3-di-di-4-(methoxyimino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazolium, (E)- or (Z)-4-(isobutoxyimino)-1,3-di- Methyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazolium, (E)- or (Z)-4-(tert-butoxyimino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazolium, (E)- or (Z)-4-(cyclopropylmethoxyimino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazolium, (E)- or (Z)-4-((allyloxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazolium, (E)- or (Z)-4-((4-methoxybenzyloxy)imino)-1,3-dimethyl-9-oxo- 4,9-Dihydro-1H-naphtho[2,3-d]imidazolium, (E)- or (Z)-4-((4-benzyloxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazolium, (E)- or (Z)-4-((4-trifluoromethylbenzyloxy)imino)-1,3-dimethyl-9-oxo 4,9-dihydro-1H-naphtho[2,3-d]imidazolium, (E)- or (Z)-4-((4-fluorobenzyloxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazolium, (E)- or (Z)-4-(perfluorobenzyloxyimino)-1,3-dimethyl-9-oxo-4,9-Dihydro-1H-naphtho[2,3-d]imidazolium, (E)- or (Z)-4-((4-nitrobenzyloxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazolium, (E)- or (Z)-4-((2-methoxyethoxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazolium, (E)- or (Z)-4-((2-(benzyloxy)ethoxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphtho[2,3-d]imidazolium, (E)- or (Z)-4-((2-(2-methoxyethoxy)ethoxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazolonium, (E)- or (Z)-4-((2-(2-(2-methoxyethoxy)ethoxy)ethoxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazolonium, (E)- or (Z)-4-((benzyloxy)imino)-1-butyl-3-methyl-9-oxo-2-(3,4,5-trimethoxyphenyl)-4,9-dihydro-1H-naphthol[2,3-d]imidazolonium, etc.

[0045] Secondly, the present invention also relates to a pharmaceutical composition comprising one or more of the aforementioned quinone oxime-imidazole derivatives and a pharmaceutically permissible carrier.

[0046] Thirdly, the present invention also relates to the use of the pharmaceutical composition described herein in the preparation of anticancer, antibacterial or antiviral drugs.

[0047] Fourthly, the present invention also relates to a (Z) or (E) fused quinone oxime imidazole derivative and its hydrochloride, represented by the following general formulas (III) and (IV);

[0048] Its structural formula is as follows:

[0049] A ring: selected from aromatic rings with or without one or more substituents, or heteroaromatic rings with or without one or more substituents;

[0050] R 1 R 3 and R 4 : Same or different, each representing - hydrogen atom, - lower chain alkyl with or without one or more substituents, - lower chain alkenyl with or without one or more substituents, - lower alkynyl with or without one or more substituents, - saturated heterocyclic with or without one or more substituents, - cycloalkyl with or without one or more substituents, - cycloalkenyl with or without one or more substituents, - aryl with or without one or more substituents, - heteroaryl with or without one or more substituents;

[0051] The above A ring and R 1 R 2 R 3 and R 4 The substituents can be selected from groups of group B;

[0052] Group B: - Lower alkyl groups with no or one or more substituents, - Lower alkenyl groups with no or one or more substituents, - Lower alkynyl groups with no or one or more substituents, - Saturated heterocyclic groups with no or one or more substituents, - Cycloalkyl groups with no or one or more substituents, - Cycloalkenyl groups with no or one or more substituents, - Aryl groups with no or one or more substituents, - Heteroaryl groups with no or one or more substituents, -OR a -SR a -O-lower alkylene-OR a -O-lower alkylene-O-lower alkylene-OR a -O-lower alkylene-O-lower alkylene-O-lower alkylene-OR a -O-lower alkylene-NR a R b -O-lower alkylene-O-lower alkylene-NR a R b -O-lower alkylene-NR c -lower alkylene-NR a R b -O-CO-NR a R b -SOR a -SO2R a -SO2NR a R b -NR a -SO2R b -NR a R b -NR c -lower alkylene-NR a R b -N(-lower alkylene-NR) a R b 2, -NO2, -CN, -halogen, -CO2R a -COO - -CONR a R b -CONR a -OR b -NR a -COR b -NR a -CO-NR b Rc -OCOR a and -COR a ;

[0053] R a R b and R c : Same or different, each representing - hydrogen atom, - lower chain alkyl with or without one or more substituents, - lower chain alkenyl with or without one or more substituents, - lower alkynyl with or without one or more substituents, - saturated heterocyclic group with or without one or more substituents, - cycloalkyl with or without one or more substituents, - cycloalkenyl with or without one or more substituents, - aryl with or without one or more substituents, - heteroaryl with or without one or more substituents; wherein, substituent refers to lower alkyl or heteroalkyl.

[0054] As one implementation scheme, in the aforementioned structural formula,

[0055] Ring A: Selected from an aromatic ring with no or one or more substituents; the substituent is NO2;

[0056] R 1 : Selected from -hydrogen atom, -no or one or more substituents of lower chain alkyl, -no or one or more substituents of lower chain alkenyl, -no or one or more substituents of lower chain alkynyl;

[0057] The substituent is selected from -cycloalkyl, -aryl, -OR a -O-lower chain alkyl-OR a -O-lower chain alkyl-O-lower chain alkyl-OR a -OR a Substituted aryl, -halogen-substituted aryl, -CF3-substituted aryl, -NO2-substituted aryl, -NH2; wherein, R a It is a lower chain alkyl group substituted with a hydrogen atom, an aryl group, a lower chain alkyl group, or an aryl-substituted lower chain alkyl group;

[0058] R 3 : indicates -hydrogen atom, -lower chain alkyl with no or one or more substituents, -cycloalkyl, -aryl, -aryl substituted with lower chain alkyl, -OR a And / or halogen-substituted aryl, -heteroaryl;

[0059] The substituent is a heteroaryl, a halogen, or a lower chain alkyl-substituted heteroaryl; R a - Lower chain alkyl;

[0060] R 4: represents -hydrogen atom, -lower chain alkyl with no or one or more substituents, -lower chain alkenyl with no or one or more substituents, -lower chain alkynyl with no or one or more substituents, -cycloalkyl, -aryl with no or one or more substituents;

[0061] The substituent is -CN, -lower chain alkyl, -halogen, or -OR. a Substituted aryl, -OR a -heteroaryl, -aryl, -halogen-substituted aryl, -CO2R a -Saturated heterocyclic group, -O-lower chain alkyl group -OR a ;R a It is a lower-chain alkyl group.

[0062] As another implementation scheme, in the aforementioned structural formula,

[0063] Ring A: Selected from an aromatic ring with no or one or more substituents; the substituent is NO2;

[0064] R 1 : Selected from -hydrogen atom, -no or one or more substituents of lower chain alkyl, -no or one or more substituents of lower chain alkenyl, -no or one or more substituents of lower chain alkynyl;

[0065] The substituent is selected from -cycloalkyl, -aryl, -OR a -O-lower chain alkyl-OR a -O-lower chain alkyl-O-lower chain alkyl-OR a -OR a Substituted aryl, -halogen-substituted aryl, -CF3-substituted aryl, -NO2-substituted aryl, -NH2; wherein, R a It is a lower chain alkyl group substituted with a hydrogen atom, an aryl group, a lower chain alkyl group, or an aryl-substituted lower chain alkyl group;

[0066] R 3 : indicates -hydrogen atom, -lower chain alkyl with no or one or more substituents, -cycloalkyl, -aryl, -aryl substituted with lower chain alkyl, -OR a And / or halogen-substituted aryl, -heteroaryl;

[0067] The substituent is a heteroaryl, a halogen, or a lower chain alkyl-substituted heteroaryl; R a - Lower chain alkyl;

[0068] R 4 : represents -hydrogen atom, -lower chain alkyl with no or one or more substituents, -lower chain alkenyl with no or one or more substituents, -lower chain alkynyl with no or one or more substituents, -cycloalkyl, -aryl with no or one or more substituents;

[0069] The substituent is -CN, -lower chain alkyl, -halogen, or -OR. a Substituted aryl, -OR a -heteroaryl, -aryl, -halogen-substituted aryl, -CO2R a -Saturated heterocyclic group, -O-lower chain alkyl group -OR a ;R a It is a lower-chain alkyl group.

[0070] As another embodiment of the present invention, in the structural formula,

[0071] Ring A: Selected from benzene rings, naphthalene rings, or NO2-substituted benzene rings;

[0072] R 1 Selected from -hydrogen atom, -C1 to C6 straight-chain alkyl or branched alkyl, -benzyl, -C3 to C6 methylcycloalkyl, -C3 to C6 alkenyl, -CH2(C6H 5-m -X m (X is a halogen atom, NO2, hydrogen atom, or -OC) n H 2n+1，n＝1～6 -CH2(C6H4-CH) n X 3-n (n = 1 to 3, X is a halogen atom), -(C n H 2n -O) y -C m H 2m+1 (n=1~6, m=1~6, y=1~3), -C n H 2n -OC m H 2m -Ph(n=1~6, m=1~6) or -C n H 2n -NH2 (n=1~6);

[0073] R 3 Selected from -hydrogen atom, -C1 to C6 straight-chain alkyl or branched-chain alkyl, -phenyl or substituted phenyl, -C4 to C6 methylcycloalkyl, -heteroaryl, -CH n X 3-n (n=1~3, X is a halogen atom), or -CH2CH2(2-CH3-furyl);

[0074] R 4Selected from -C1 to C6 straight-chain alkyl or branched-chain alkyl, -C3 to C6 methylcycloalkyl, -lower alkylene-O-lower alkyl, -C3 to C6 alkenyl, -alkynyl, -heteroaryl, -benzyl or substituted benzyl, -ester or substituted ester, -phenyl or substituted phenyl, -cyano, -CH2(thienyl), -CH2CH(-OCH2CH2O-) or -CH2(pyrazinyl).

[0075] As another embodiment of the present invention, in the structural formula,

[0076] Ring A: Selected from benzene rings, naphthalene rings, or NO2-substituted benzene rings;

[0077] R 1 Selected from -hydrogen atom, -C1 to C6 straight-chain alkyl or branched alkyl, -benzyl, -C3 to C6 methylcycloalkyl, -C3 to C6 alkenyl, -CH2(C6H 5-m -X m (X is a halogen atom, NO2, hydrogen atom, or -OC) n H 2n+1，n＝1～6 -CH2(C6H4-CH) n X 3-n (n = 1 to 3, X is a halogen atom), -(C n H 2n -O) y -C m H 2m+1 (n=1~6, m=1~6, y=1~3), -C n H 2n -OC m H 2m -Ph(n=1~6, m=1~6) or -C n H 2n -NH2 (n=1~6);

[0078] R 3 Selected from straight-chain alkyl or branched alkyl groups with -hydrogen atom and -C1 to C6 atom;

[0079] R 4 Selected from -C1 to C6 straight-chain alkyl or branched-chain alkyl, -lower alkylene-O-lower alkyl, -C3 to C6 alkenyl, -ester or substituted ester, -phenyl or substituted phenyl, -cyano.

[0080] In another embodiment of the present invention, the derivatives include (E)-9-(hydroxyimino)-3-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-3-ethyl-9-(hydroxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-3-propyl-9-(hydroxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-3-butyl-9-(hydroxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, and (E)-3-isopropyl-9-(hydroxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one. (E)-3-isobutyl-9-(hydroxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-(2-methylbutyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-(4-methoxybenzyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-(2-methoxyethyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-(3-methyl-2-en-1-yl ... [2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-(propyl-2-yn-1-yl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-(thiophen-2-ylmethyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-benzyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-(2-fluorobenzyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-(3-fluorobenzyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-(3-fluorobenzyl)-3,9-dihydro-4H- Naphthol [2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-(4-fluorobenzyl)-3,9-dihydro-4H-naphthol [2,3-d]imidazol-4-one, (E)-2-(4-(hydroxyimino)-9-oxo-4,9-dihydro-1H-naphthol [2,3-d]imidazol-1-yl)acetate, (E)-3-((1,3-dioxane-2-yl)methyl)-9-(hydroxyimino)-3,9-dihydro-4H-naphthol [2,3-d]imidazol-4-one, (E)-11-(hydroxyimino)-3-methyl-3,11-dihydro-4H-anthraquinone [2,3-d]imidazol-4-one, (E)-11-(hydroxyimino)-3-ethyl-3,11-Dihydro-4H-anthraquinone[2,3-d]imidazol-4-one, (E)-3-cyclopropyl-9-(hydroxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-3-tert-butyl-9-(hydroxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-(pyrazin-2-ylmethyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-benzyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-benzyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-(2,4,6-trimethylphenyl)-3, 9-Dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-(2-fluorophenyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-(3-fluorophenyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-(4-fluorophenyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-(4-methoxyphenyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-(3-chloro-4- (E)-9-(hydroxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-(3-bromo-4-fluorophenyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-3-methyl-8-nitro-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-(hydroxyimino)-2,3-dimethyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-3-butyl-9-(hydroxyimino)-2-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-11-(hydroxyimino) -2,3-Dimethyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one, (E)-3-ethyl-11-(hydroxyimino)-2-methyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one, (E)-3-isobutyl-11-(hydroxyimino)-2-methyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one, (E)-11-(hydroxyimino)-2-methyl-3-(3-methyl-2-en-1-yl)-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one, (E)-2-(4-(hydroxyimino)-2-methyl-11-oxo-4,11-dihydro-1H-anthraquinone[2,3-d]imidazol-4-one, (E)-2-(4-(hydroxyimino)-2-methyl-11-oxo-4,11-dihydro-1H-anthraquinone[2,3-d]imidazol-4-one,[3-d]imidazol-1-yl)acetonitrile, (E)-3-benzyl-11-(hydroxyimino)-2-methyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one, (E)-3-(4-fluorobenzyl)-11-(hydroxyimino)-2-methyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one, (E)-3-butyl-9-(hydroxyimino)-2-ethyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-3-butyl-9-(hydroxyimino)-2-propyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-2-(sec-butyl)-3-butyl-9-(hydroxyimino)-2-propyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-2-(sec-butyl)-3-butyl-9-(hydroxyimino)-2-ethyl ... (E)-3,9-dihydro-4H-naphthol [2,3-d]imidazol-4-one, (E)-3-butyl-9-(hydroxyimino)-2-isobutyl-3,9-dihydro-4H-naphthol [2,3-d]imidazol-4-one, (E)-3-butyl-9-(hydroxyimino)-2-(pentan-3-yl)-3,9-dihydro-4H-naphthol [2,3-d]imidazol-4-one, (E)-3-butyl-9-(hydroxyimino)-2-tert-butyl-3,9-dihydro-4H-naphthol [2,3-d]imidazol-4-one, (E)-3-butyl-9-(hydroxyimino)-2-(2-(5-methylfuran-2-yl)ethyl)-3,9-dihydro-4H-naphthol [2,3-d] Imidazol-4-one, (E)-3-butyl-9-(hydroxyimino)-2-cyclobutyl-3,9-dihydro-4H-naphthol [2,3-d]imazol-4-one, (E)-3-butyl-9-(hydroxyimino)-2-phenyl-3,9-dihydro-4H-naphthol [2,3-d]imazol-4-one, (E)-3-butyl-9-(hydroxyimino)-2-(4-isopropylphenyl)-3,9-dihydro-4H-naphthol [2,3-d]imazol-4-one, (E)-3-butyl-9-(hydroxyimino)-2-(3,4,5-trimethoxyphenyl)-3,9-dihydro-4H-naphthol [2,3-d]imazol-4-one, (E)-3-butyl-2-(3-chloro-4-methyl (E)-3-butyl-9-(hydroxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-3-butyl-9-(hydroxyimino)-2-naphthyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-3-butyl-9-(hydroxyimino)-2-(trifluoromethyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-3-butyl-9-(hydroxyimino)-2-(furan-2-yl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-3-butyl-9-(hydroxyimino)-2-(thiophen-2-yl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-3-butyl-9-(hydroxyimino)-2-(thiophen-2-yl)-3,9-dihydro-4H-naphthol[2,3-d][3-d]imidazol-4-one, (E)-2-ethyl-11-(hydroxyimino)-3-methyl-3,11-dihydro-4H-anthraquinone [2,3-d]imidazol-4-one, (E)-2-(furan-2-yl)-11-(hydroxyimino)-3-methyl-3,11-dihydro-4H-anthraquinone [2,3-d]imidazol-4-one, (E) and (Z)-9-(methoxyimino)-3-methyl-3,9-dihydro-4H-naphthol [2,3-d]imidazol-4-one, (E) and (Z)-9-(ethoxyimino)-3-methyl-3,9-dihydro-4H-naphthol [2,3-d]imidazol-4-one, (E) and (Z)-9-(benzyloxyimino)-3-methyl 3,9-dihydro-4H-naphthol [2,3-d]imidazol-4-one, (E) and (Z)-9-(isopropoxyimino)-3-methyl-3,9-dihydro-4H-naphthol [2,3-d]imidazol-4-one, (E) and (Z)-9-(butoxyimino)-3-methyl-3,9-dihydro-4H-naphthol [2,3-d]imidazol-4-one, (E) and (Z)-9-(isobutoxyimino)-3-methyl-3,9-dihydro-4H-naphthol [2,3-d]imidazol-4-one, (E) and (Z)-9-(tert-butoxyimino)-3-methyl-3,9-dihydro-4H-naphthol [2,3-d]imidazol-4-one, (E) and (Z)-9-((cyclo (2,3-d)-9-((allyloxy)imino)-3-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E) and (Z)-3-methyl-9-(((4-methoxybenzyl)oxy)imino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E) and (Z)-3-methyl-9-(((4-chlorobenzyl)oxy)imino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E) and (Z)-3-methyl-9-(((4-trifluoromethylbenzyl)oxy)imino) (E) and (Z)-3-methyl-9-(((4-fluorobenzyl)oxy)imino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E) and (Z)-3-methyl-9-(((4-nitrobenzyl)oxy)imino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E) and (Z)-3-methyl-9-(((4-nitrobenzyl)oxy)imino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E) and (Z)-11-(benzyloxyimino)-3-methyl-3,11-dihydro-4H-anthraquinone[2,[3-d]imidazol-4-one, (E) and (Z)-11-(butoxyimino)-3-methyl-3,11-dihydro-4H-anthraquinone [2,3-d]imidazol-4-one, (E) and (Z)-11-(tert-butoxyimino)-3-methyl-3,11-dihydro-4H-anthraquinone [2,3-d]imidazol-4-one, (E)-9-((2-methoxyethoxy)imino)-3-methyl-3,9-dihydro-4H-naphthol [2,3-d]imidazol-4-one, (E) and (Z)-9-((2-(benzyloxy)ethoxy)imino)-3-methyl-3,9-dihydro-4H-naphthol [2,3-d]imidazol-4-one, (E) and (Z)-9-((2-(benzyloxy)ethoxy)imino)-3-methyl-3,9-dihydro-4H-naphthol [2, [3-d]imidazol-4-one, (E)-9-((2-(2-methoxyethoxy)ethoxy)imino)-3-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E) and (Z)-9-((2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)imino)-3-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E)-9-((3-aminopropoxy)imino)-3-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E) and (Z)-3-butyl-9-(methoxyimino)- 3,9-Dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E) and (Z)-3-butyl-9-(ethoxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E) and (Z)-9-((benzyloxy)imino)-3-butyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E) and (Z)-11-((methoxy)imino)-3-(2-(2-methoxyethoxy)ethyl)-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one, (E) and (Z)-9-((benzyloxy)imino)- 2,3-Dimethyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E) and (Z)-11-((benzyloxy)imino)-2,3-dimethyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one, (E) and (Z)-9-((benzyloxy)imino)-3-butyl-2-(3,4,5-trimethoxyphenyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one, (E) and (Z)-2-cyclopropyl-11-(methoxyimino)-3-methyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one.

[0081] The (Z) or (E) fused quinone oxime imidazole derivatives and their hydrochlorides, represented by general formulas (III) and (IV), are synthetic intermediates of the above general formulas (I) and (II), and themselves possess excellent antitumor activity. Therefore, in a fifth aspect, the present invention also relates to a pharmaceutical composition comprising the compound or its hydrochloride, and a pharmaceutically permissible carrier. It possesses anticancer, antibacterial, and antiviral activities.

[0082] Fifthly, the present invention relates to the use of the above-mentioned pharmaceutical composition in the preparation of anticancer, antibacterial or antiviral drugs.

[0083] The compounds of general formulas (I), (II), (III) and (IV) will be further described below.

[0084] The term "lower" refers to a straight-chain or branched hydrocarbon chain with 1-6 carbon atoms. "Lower alkyl" is generally an alkyl group with 1-4 carbon atoms, with methyl, ethyl, propyl, isopropyl, butyl, and isobutyl being particularly preferred. "Lower alkenyl" is generally vinyl, allyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, and 3-methyl-2-butenyl. "Lower alkynyl" is generally ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, and 1-methyl-2-propynyl. "Aryl" refers to an aromatic group, preferably an aryl group with 6-14 carbon atoms, with phenyl, naphthyl, and fluorenyl being the most preferred. Additionally, the A ring refers to the ring forming the aforementioned aryl groups, with phenyl and naphthyl being the most preferred. "Heteroaromatic ring" refers to a 5-6 member monocyclic heteroaryl group having 1-4 heteroatoms selected from N, S, and O, as well as a bicyclic heteroaryl group formed by fusion of these heteroatoms with a benzene ring or a 5-6 member monocyclic heteroaryl group. In this case, the 5-6 membered monocyclic heteroaryl group is preferably furanyl, thiopheneyl, pyrroleyl, imidazolyl, thiazolyl, pyrazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl, and the bicyclic heteroaryl group is preferably benzofuranyl, benzothiopheneyl, benzothiadiazolyl, benzothiazolyl, benzooxazolyl, benzooxadiazolyl, benzoimidazolyl, indolyl, isoindolyl, indolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, benzo-m-dioxacyclopentenyl, indoleyl, imidazopyridyl, and zolinyl. Partially saturated heteroaryl groups are also suitable, such as 1,2,3,4-tetrahydroquinolinyl. Furanyl and thiopheneyl are more preferred.

[0085] "Lower heteroalkyl" refers to an alkyl group having 1 to 4 carbon atoms selected from one or more of the heteroatoms N, S and O.

[0086] "Cycloalkyl" refers to cycloalkyl groups with 3-10 carbon atoms, with cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl being particularly preferred. "Cycloalkenyl" is preferably a cycloalkenyl group with 3-8 carbon atoms.

[0087] There are no particular restrictions on the "counter anion", as long as the counter anion of the imidazolium cation is a pharmaceutically acceptable anion. Preferably, it is a monovalent or divalent anion such as halide ions, organic sulfonate ions, acetate ions, trifluoroacetate ions, carbonate ions, and sulfate ions, etc., with halide ions being the best.

[0088] "Heterocyclic group" refers to a 5-7 member monocyclic saturated heterocycle or its bridged ring having 1-4 heteroatoms selected from N, S and O. Preferred groups are tetrahydropyranyl, tetrahydrofuranyl, pyrrolidinyl, piperazineyl, aziridine heptyl, diaziridine heptyl, quininecycloyl, piperidinyl and morpholinyl.

[0089] The compounds of the present invention exist as tautomers of the following formula due to the delocalization of cations. The present invention also includes isolated tautomers or mixtures thereof. Therefore, in the present invention, compounds represented by 1H-imidazol-3-onium derivatives also include the tautomer of 3H-imidazol-1-onium derivatives and a mixture of the two isomers.

[0090]

[0091] In addition, the hydrochloride salts of (III) and (IV) of the present invention are also included in the present invention.

[0092] In some cases, depending on the type of substituent, compounds (I), (II), (III), and (IV) of the present invention exist as geometric isomers and tautomers. Separate forms of these isomers or mixtures thereof are included within the scope of this invention. Furthermore, since the compounds of the present invention have asymmetric carbon atoms, isomers donating these asymmetric carbon atoms exist; the present invention includes mixtures and separate forms of these optical isomers. Additionally, in some cases, due to the type of substituent, the compounds of the present invention form N-oxides, which are also included within the scope of this invention; the present invention also includes various hydrates, solvates, and polymorphs of compounds (I), (II), (III), and (IV) of the present invention.

[0093] Sixthly, the present invention also relates to a method for preparing the aforementioned quinone oxime imidazoline derivative and its synthetic intermediate, the method comprising the following steps:

[0094] A. Substituted quinone imidazole derivatives using proton solvents and R 1 ONH2·HCl reacts with a weak base or with the corresponding R under the catalysis of a weak base. 1 ONH2 undergoes an oxime reaction in the presence of a weak base hydrochloride to yield a quinone oxime imidazole derivative.

[0095] B. Quinoxime imidazole derivatives (III) or (IV) reacting with the corresponding halogenated reagent R in an organic solvent. 2 X undergoes an N-alkylation reaction to yield quinone oxime imidazolium derivatives (I) or (II).

[0096] Preferably, in step A,

[0097] The molar ratio of the substituted naphthoquinone imidazole, the substituted oxamyl hydrochloride R1ONH2·HCl, and the weak base is 1:1.2-5:0.001-0.01.

[0098] Preferably, the substituted oxyamine hydrochloride is selected from hydroxylamine hydrochloride, methoxyamine hydrochloride, phenoxyamine hydrochloride, and benzyloxyamine hydrochloride.

[0099] Preferably, in step A, the weak base is selected from potassium carbonate, triethylamine, pyridine, etc.

[0100] Preferably, in step A, the proton solvent is selected from methanol, ethanol, and isopropanol.

[0101] Preferably, in step A, the reaction temperature is 90–125°C and the reaction time is 12–48 hours.

[0102] Preferably, in step B, the molar ratio of the quinone oxime imidazole derivative (III) or (IV) to the halogenated reagent R2X is 1:1 to 1:100.

[0103] Preferably, in step B, the haloalkane is selected from iodomethane, iodoethane, etc.

[0104] Preferably, in step B, the organic solvent is selected from acetonitrile, ethyl acetate, tetrahydrofuran, etc.

[0105] Preferably, in step B, the reaction temperature is 50–120°C and the reaction time is 8–48 hours.

[0106] Compounds (III) and (IV) of this invention can be used as broad-spectrum anticancer drugs, as well as antibacterial and antiviral drugs, with low toxicity and good safety. Therefore, the compounds of this invention have proliferative inhibitory effects on all solid tumors and lymphomas, especially breast cancer, cervical cancer, non-small cell lung cancer, rectal cancer, liver cancer, leukemia, prostate cancer, ovarian cancer, myeloma, esophageal cancer, pancreatic cancer, bladder cancer, melanoma, gastric cancer, and other tumors.

[0107] The pharmaceutical compositions of the present invention can be prepared by conventional methods using one or more compounds shown in general formulas (III) and (IV) and pharmaceutically permissible carriers (drug carriers, excipients, etc.) commonly used in the art. Administration can be performed orally in the form of tablets, pills, capsules, granules, powders, liquids, inhalers, etc., or non-oral in the form of injections, suppositories, eye drops, eye ointments, transdermal liquids, ointments, transdermal patches, transmucosal liquids, transmucosal patches, etc., via intravenous or intramuscular injection.

[0108] As a solid composition for oral administration according to the present invention, tablets, powders, granules, etc., are available. In these solid compositions, one or more active substances are mixed with at least one inert excipient (such as lactose, mannitol, glucose, hydroxypropyl cellulose, microcrystalline cellulose, starch, polyvinylpyrrolidone, magnesium aluminum metasilicate, etc.). Following conventional procedures, the compound may contain inert additives such as lubricants (such as magnesium stearate), disintegrants (such as sodium carboxymethyl starch), and solubilizers. If necessary, tablets or pills may be coated with sugar-coating or gastric-soluble or enteric-soluble coating agents.

[0109] Liquid compositions for oral administration include pharmaceutically permissible emulsions, liquids, suspensions, syrups, elixirs, etc., and contain commonly used inert solvents such as purified water or ethanol. In addition to inert solvents, the composition may also contain solubilizers, wetting agents, suspending agents, sweeteners, flavoring agents, aromatizers, and preservatives.

[0110] Injectable formulations intended for non-oral administration contain sterile aqueous or aqueous solvents, suspensions, and emulsions. Examples of water-soluble agents include distilled water for injection and physiological saline. Insoluble agents include propylene glycol, polyethylene glycol, vegetable oils such as olive oil, alcohols such as ethanol, and polysorbate 80. These compositions may also contain isotonic agents, preservatives, wetting agents, emulsifiers, dispersants, stabilizers, and co-solvents. These compositions are sterilized, for example, by means of sterile membrane filtration, mixing with a bactericide, or irradiation. Furthermore, they can be formulated as sterile solid compositions, dissolved or suspended in sterile water or sterile solvents for injection before use.

[0111] Compared with the prior art, the present invention has the following beneficial effects:

[0112] 1. This invention systematically modifies the quinone imidazole skeleton to obtain a series of novel quinone oxime imidazole derivatives and quinone oxime quinone imidazole derivatives.

[0113] 2. This invention employs a novel preparation method that is simpler to synthesize, uses more readily available raw materials, is low in cost, and is suitable for large-scale preparation. Detailed Implementation

[0114] The following examples will help those skilled in the art to further understand the present invention, but do not limit the invention in any way. It should be noted that those skilled in the art can make several adjustments and improvements without departing from the concept of the present invention. These all fall within the scope of protection of the present invention. The compounds of the present invention are by no means limited to the compounds described in the following examples. Experimental methods in the following examples, unless specific conditions are specified, are generally performed under conventional conditions or according to the manufacturer's recommendations. Furthermore, the synthesis of the starting material compounds of the compounds of the present invention is shown in the examples.

[0115] Example 1

[0116] 2,3,-Diamino-1,4-benzoquinone (20 g) was dissolved in 100 mL of formic acid and refluxed for 6 hours. After cooling to room temperature, the solution was poured into an ice-water mixture. Ammonia was added to adjust the pH to 9-10. The mixture was filtered and dried under vacuum to obtain a yellow solid, 1,4-naphthoquinone imidazole (22 g). 1,4-naphthoquinone imidazole (0.3 g) and potassium hydroxide (0.15 g) were added sequentially to a dimethyl sulfoxide solution (3 mL). The mixture was stirred at 50°C for 30 minutes. Iodomethane (0.2 mL) was added, and after reacting for 2 hours, water was added to precipitate the solid. The solid was filtered, washed with water, and dried under vacuum to obtain a yellow solid, 2-methyl-1,4-naphthoquinone imidazole (0.31 g). 2-Methylnaphthoquinone imidazole (0.21 g), hydroxylamine hydrochloride (0.35 g), and pyridine (0.8 mL) were dissolved in ethanol (70 mL) and reacted at 90 °C for 48 hours. After the reaction was completed, a solid precipitated in the solution. The solid was directly filtered and dried under vacuum to obtain a pale yellow solid (0.15 g), which is compound 1.

[0117] Compound 1:

[0118]

[0119] (E)-9-(hydroxyimino)-3-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0120] 1 H NMR (400MHz, DMSO-d6) δ13.01(s,1H),8.26(d,J=0.8Hz,2H),8.07(dd,J=8.0,4.0Hz,1H),7.72-7.64(m,1H),7.61-7.52(m,1H),4.00(s,3H).

[0121] 13C NMR (101MHz, DMSO-d6) δ175.27,145.22,140.18,139.62,133.71,133.06,131.04,129.58,127.17,126.12,123.92,34.14.

[0122] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 228.0768, measured value: 228.0771.

[0123] Compounds 2-20 can be prepared by reacting 1,4-naphthoquinone imidazole with substituted haloalkanes using the method of Example 1. The reactants and reaction conditions for other compounds remain unchanged, and all raw materials are commercially available.

[0124] Compound 2:

[0125]

[0126] (E)-3-ethyl-9-(hydroxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0127] 1 H NMR (400MHz, DMSO-d6) δ13.04(s,1H),8.36(s,1H),8.26(d,J=8.0Hz,1H),8.10(d,J=8.0Hz, 1H),7.72-7.64(m,1H),7.60(t,J=7.2Hz,1H),4.46(q,J=7.2Hz,2H),1.39(t,J=8.0Hz,3H).

[0128] 13 C NMR (101MHz, DMSO-d6) δ174.94,144.31,140.21,140.08,133.66,133.06,131.10,129.59,126.48,126.22,123.91,42.17,16.64.

[0129] HRMS(ESI): Theoretical value of m / z: C 13 H 11 N3O2[M+H] + 242.0924, measured value: 242.0927.

[0130] Compound 3:

[0131]

[0132] (E)-3-propyl-9-(hydroxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0133] (E)-3-propyl-9-(hydroxyimino)-3,9-dihydro-4H-naphtho[2,3-d]imidazol-4-one

[0134] 1 H NMR (400MHz, DMSO-d6) δ13.05(s,1H),8.34(s,1H),8.26(d,J=8.0Hz,1H),8.09(dd,J=8.0,1.0Hz,1H),7.72 -7.65(m,1H),7.59(td,J=8.0,1.0Hz,1H),4.39(t,J=8.0Hz,2H),1.85-1.72(m,2H),0.83(t,J=7.4Hz,3H).

[0135] 13 C NMR (101MHz, DMSO-d6) δ174.99,144.84,140.20,140.05,133.64,133.05,131.11,129.58,126.57,126.21,123.89,48.30,23.97,11.02.

[0136] HRMS(ESI): Theoretical value of m / z: C 14 H 13 N3O2[M+H] + 256.1081, Measured value: 256.1084.

[0137] Compound 4:

[0138]

[0139] (E)-3-Butyl-9-(hydroxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0140] (E)-3-butyl-9-(hydroxyimino)-3,9-dihydro-4H-naphtho[2,3-d]imidazol-4-one

[0141] 1H NMR (400MHz, DMSO-d6) δ13.05(s,1H),8.34(s,1H),8.26(dd,J=8.0,1.2Hz,1H),8.09(dd,J=8.0,1.2Hz,1H),7.67(td,J=4.0 ,1.6Hz,1H),7.59(td,J=8.0,1.2Hz,1H),4.42(t,J=8.0Hz,2H),1.81-1.66(m,2H),1.30-1.19(m,2H),0.86(t,J=8.0Hz,3H).

[0142] 13 C NMR (101MHz, DMSO-d6) δ174.97,144.77,140.20,140.03,133.63,133.04,131.11,129.57,126.54,126.22,123.89,46.55,32.70,19.48,13.84.

[0143] HRMS(ESI): Theoretical value of m / z: C 15 H 15 N3O2[M+H] + 270.1237, Measured value: 270.1240.

[0144] Compound 5:

[0145]

[0146] (E)-3-Isopropyl-9-(hydroxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one 1 H NMR (400MHz, DMSO-d6) δ13.12(s,1H),8.52(s,1H),8.26(d,J=8.0Hz,1H),8.11(dd,J=8.0,1.6H z,1H),7.73-7.63(m,1H),7.59(td,J=8.0,1.2Hz,1H),5.39-5.25(m,1H),1.51(d,J=8.0Hz,6H).

[0147] 13 C NMR (101MHz, DMSO-d6) δ174.95,141.88,140.23,140.16,133.33,133.04,131.27,129.61,126.36,126.16,123.78,49.64,23.06.

[0148] Compound 6:

[0149]

[0150] (E)-3-Isobutyl-9-(hydroxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one 1 H NMR (400MHz, DMSO-d6) δ13.05(s,1H),8.33(s,1H),8.27(dd,J=8.0,1.2Hz,1H),8.10(dd,J=8.0,1.4Hz,1H),7.68( td,J=8.0,1.4Hz,1H),7.59(td,J=8.0,1.2Hz,1H),4.26(d,J=8.0Hz,2H),2.17-2.02(m,1H),0.84(d,J=4.0Hz,6H).

[0151] 13 C NMR (101MHz, DMSO-d6) δ175.08,145.17,140.19,140.03,133.64,133.07,131.13,129.59,126.69,126.22,123.90,53.53,29.52,19.75.

[0152] HRMS(ESI): Theoretical value of m / z: C 15 H 15 N3O2[M+H] + 270.1237, Measured value: 270.1237.

[0153] Compound 7:

[0154]

[0155] (E)-9-(hydroxyimino)-3-(2-methylbutyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one 1 HNMR(400MHz, DMSO-d6)δ13.05(s,1H),8.33(s,1H),8.27(dd,J=8.0,1.2Hz,1H),8.10(dd,J=8.0,1.4Hz,1H),7.71-7.64(m,1H),7.60(td,J=8.0,1.2 Hz,1H),4.43-4.35(m,1H),4.24-4.16(m,1H),1.99-1.83(m,1H),1.37-1. 20(m,1H),1.17-1.07(m,1H),0.85(t,J=8.0Hz,3H),0.77(d,J=4.0Hz,3H).

[0156] 13 C NMR(101MHz,DMSO-d6)δ175.08,159.51,145.25,140.19,140.05,133.65,133.0 8,131.14,129.60,126.72,126.25,123.90,52.24,35.68,26.51,16.57,11.31.

[0157] HRMS(ESI): Theoretical value of m / z: C 16 H 17 N3O2[M+H] + 284.1394, Measured value: 284.1390.

[0158] Compound 8:

[0159]

[0160] (E)-9-(hydroxyimino)-3-(4-methoxybenzyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one 1 H NMR (400MHz, DMSO-d6) δ13.03(s,1H),8.48(s,1H),8.27(d,J=8.0Hz,1H),8.09(dd,J=8.0,1.2Hz,1H),7 .68(td,J=8.0,1.2Hz,1H),7.62-7.55(m,1H),7.28(d,J=8.0Hz,2H),6.86(d,J=8.0Hz,2H),5.62(s,2H).

[0161] 13 C NMR(101MHz,DMSO-d6)δ175.10,159.52,159.38,144.87,140.11,133.77,133.14 ,131.03,129.59,129.50,129.35,126.36,126.22,123.96,114.49,55.52,49.10.

[0162] HRMS(ESI): Theoretical value of m / z: C 19 H 15 FN3O3[M+H] + 334.1186, measured value: 334.1182.

[0163] Compound 9:

[0164]

[0165] (E)-9-(hydroxyimino)-3-(2-methoxyethyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one 1 H NMR (400MHz, DMSO-d6) δ13.04(s,1H),8.30-8.23(m,2H),8.09(dd,J=8.0,1.4Hz,1H),7.68(td,J=8. 0,1.4Hz,1H),7.59(td,J=8.0,1.2Hz,1H),4.61(t,J=5.2Hz,2H),3.68(t,J=4.0Hz,2H),3.20(s,3H).

[0166] 13 C NMR (101MHz, DMSO-d6) δ175.16,145.37,140.16,139.96,133.69,133.09,131.05,129.57,126.48,126.20,123.93,70.72,58.48,46.46.

[0167] HRMS(ESI): Theoretical value of m / z: C 14 H 13 N3O3[M+H] + 272.1030, Measured value: 272.1032.

[0168] Compound 10:

[0169]

[0170] (E)-9-(hydroxyimino)-3-(3-methyl-2-en-1-yl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0171] 1 H NMR (400MHz, DMSO-d6) δ13.03(s,1H),8.32(s,1H),8.26(dd,J=8.0,1.2Hz,1H),8.10(dd,J=8.0,1.4Hz,1H),7.68(td ,J=8.0,1.4Hz,1H),7.59(td,J=8.0,1.2Hz,1H),5.44-5.35(m,1H),5.06(d,J=8.0Hz,2H),1.77(s,3H),1.67(s,3H).

[0172] 13C NMR(101MHz,DMSO-d6)δ175.05,144.24,140.17,139.91,137.77,133.66,13 3.07,131.08,129.58,126.45,126.23,123.92,119.76,44.64,25.77,18.42.

[0173] HRMS(ESI): Theoretical value of m / z: C 16 H 15 N3O2[M+H] + 282.1237, measured value: 282.1239.

[0174] Compound 11:

[0175]

[0176] (E)-9-(hydroxyimino)-3-(propyl-2-yn-1-yl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0177] 1 H NMR (400MHz, DMSO-d6) δ13.02(s,1H),8.41(s,1H),8.28(d,J=8.0Hz,1H),8.11( d,J=8.0Hz,1H),7.73-7.64(m,1H),7.64-7.54(m,1H),5.35(s,2H),3.53(s,1H).

[0178] 13 C NMR (101MHz, DMSO-d6) δ175.02,144.29,139.99,133.91,133.22,130.86,129.61,129.58,126.61,126.12,124.05,78.38,77.22,36.50.

[0179] HRMS(ESI): Theoretical value of m / z: C 14 H9N3O2[M+H] + 252.0768, measured value: 252.0769.

[0180] Compound 12:

[0181]

[0182] (E)-9-(hydroxyimino)-3-(thiophen-2-ylmethyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0183] 1 H NMR (400MHz, DMSO-d6) δ13.01(s,1H),8.49(s,1H),8.27(d,J=8.0,1H),8.12(dd,J=7.9,1.5Hz,1H),7.69(t,J=8.0 ,1H),7.60(t,J=8.0Hz,1H),7.43(d,J=8.0Hz,1H),7.19(d,J=4.0Hz,1H),6.95(dd,J=8.0,4.0Hz,1H),5.88(s,2H).

[0184] 13 C NMR(101MHz,DMSO-d6)δ175.20,144.72,140.04,139.91,139.42,133.87,133 .20,130.93,129.60,127.89,127.49,127.25,126.19,126.18,124.02,44.36.

[0185] HRMS(ESI): Theoretical value of m / z: C 16 H 11 N3O2S[M+H] + 310.0645, measured value: 310.0642.

[0186] Compound 13:

[0187]

[0188] (E)-9-(hydroxyimino)-3-benzyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0189] 1 H NMR (400MHz, DMSO-d6) δ13.05(s,1H),8.51(s,1H),8.27(dd,J=8.0,1.2Hz,1H),8.07(dd,J=8.0,1.4Hz,1H),7.67(td,J=8.0 1.4Hz,1H),7.57(td,J=8.0,1.2Hz,1H),7.39-7.10(m,5H),5.70(s,2H).

[0190] 13C NMR(101MHz,DMSO-d6)δ175.08,145.10,140.10,140.06,137.44,133.81,133 .14,130.98,129.56,129.12,128.25,127.72,126.48,126.18,123.97,49.58.

[0191] HRMS(ESI): Theoretical value of m / z: C 18 H 13 N3O2[M+H] + 304.1081, measured value: 304.1082.

[0192] Compound 14:

[0193]

[0194] (E)-9-(hydroxyimino)-3-(2-fluorobenzyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0195] 1 H NMR (400MHz, DMSO-d6) δ13.04(s,1H),8.41(s,1H),8.31-8.22(m,1H),8.04(dd,J=8.0,1.4Hz,1H),7.70-7.64(m,1H),7.62 -7.54(m,1H),7.35-7.27(m,1H),7.25-7.18(m,1H),7.10(td,J=7.5,1.2Hz,1H),7.04(td,J=8.0,1.8Hz,1H),5.77(s,2H).

[0196] 13 C NMR(101MHz,DMSO-d6)δ175.00,163.05(160.71,J=234.0Hz),145.45,140.08 ,139.99,133.88,133.16,130.90,130.45(130.37,J=8.0Hz),129.56,129.35 (129.31, J = 4.0Hz), 126.66, 126.15, 125.19 (125.15, J = 4.0Hz), 124.45 (124. 31, J=14.0Hz), 123.99, 115.92 (115.71, J=21.0Hz), 44.17 (44.12, J=5.0Hz).

[0197] HRMS(ESI): Theoretical value of m / z: C 18 H12 FN3O2[M+H] + 322.0986, measured value: 322.0984.

[0198] Compound 15:

[0199]

[0200] (E)-9-(hydroxyimino)-3-(3-fluorobenzyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0201] 1 H NMR (400MHz, DMSO-d6) δ8.51(s,1H),8.27(d,J=8.0Hz,1H),8.07(d,J=8.0Hz,1H),7.68(t ,J=8.0Hz,1H),7.58(t,J=8.0Hz,1H),7.40-7.30(m,1H),7.17-7.06(m,3H),5.71(s,2H).

[0202] 13 C NMR(101MHz,DMSO-d6)δ175.12,163.82(161.39,J=243.0Hz),145.17,140.22 (140.15, J=7.0Hz), 140.10, 133.87, 133.17, 131.22 (131.14, J= 8.0Hz), 130. 95,129.56,126.63,126.47,126.18,123.99,123.75(123.72,J=3.0Hz),115. 21 (115.00, J = 21.0Hz), 114.78 (114.56, J = 22.0Hz), 49.06 (49.05, J = 1.0Hz).

[0203] Compound 16:

[0204]

[0205] (E)-9-(hydroxyimino)-3-(4-fluorobenzyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0206] 1H NMR (400MHz, DMSO-d6) δ13.04(s,1H),8.51(s,1H),8.27(dd,J=8.0,1.2Hz,1H),8.07(dd,J=8.0,1.4Hz,1H), 7.68(td,J=8.0,1.4Hz,1H),7.58(td,J=8.0,1.2Hz,1H),7.39-7.31(m,2H),7.18-7.07(m,2H),5.68(s,2H).

[0207] 13 C NMR(101MHz,DMSO-d6)δ175.11,163.34(160.91,J=243.0Hz),145.01,140.13,140.09,133.83,133.65(133.62,J=3.0 Hz), 133.15, 130.96, 130.15 (130.07, J = 8.0Hz), 129.56, 126.40, 126.19, 123.97, 116.03 (115.81, J = 22.0Hz), 48.87.

[0208] HRMS(ESI): Theoretical value of m / z: C 18 H 12 FN3O2[M+H] + 322.0986, Measured value: 322.0986.

[0209] Compound 17:

[0210]

[0211] (E)-2-(4-(hydroxyimino)-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-1-yl)acetate

[0212] 1 H NMR (400MHz, DMSO-d6) δ13.01 (s, 1H), 8.31-8.25 (m, 2H), 8.06 (dd, J = 8.0, 0.8Hz, 1H), 7.70 (td, J = 8. 0,1.2Hz,1H),7.60(td,J=8.0,0.8Hz,1H),5.32(s,2H),4.15(q,J=7.2Hz,2H),1.19(t,J=7.2Hz,3H).

[0213] 13C NMR (101MHz, DMSO-d6) δ175.27,168.10,145.42,134.05,133.27,130.71,129.61,127.16,126.61,126.05,124.13,61.78,48.16,14.47.

[0214] HRMS(ESI): Theoretical value of m / z: C 15 H 13 N3O4[M+H] + 300.0979, Measured value: 300.0981.

[0215] Compound 18:

[0216]

[0217] (E)-3-((1,3-dioxane-2-yl)methyl)-9-(hydroxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0218] 1 H NMR (400MHz, DMSO-d6) δ13.03(s,1H),8.30-8.20(m,2H),8.09(dd,J=8.0,1.4Hz,1H),7.68(td,J=8.0,1 .4Hz,1H),7.59(td,J=8.0,1.2Hz,1H),5.20(t,J=4.0Hz,1H),4.67(d,J=4.0Hz,2H),3.82-3.73(m,4H).

[0219] 13 C NMR (101MHz, DMSO-d6) δ175.26,145.49,140.06,139.55,133.72,133.12,131.03,129.58,126.88,126.19,123.95,101.10,65.05,48.12.

[0220] HRMS(ESI): Theoretical value of m / z: C 15 H 13 N3O4[M+H] + 300.0979, measured value: 300.0978.

[0221] Compound 19:

[0222]

[0223] (E)-11-(hydroxyimino)-3-methyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one

[0224] 1 H NMR (400MHz, DMSO-d6) δ13.09(s,1H),9.04(s,1H),8.77(d,J=12.4Hz,2H),8.15(dd,J=26.4,7.7Hz,2H),7.64(d,J=20.0Hz,2H),4.03(s,3H).

[0225] HRMS(ESI): Theoretical value of m / z: C 15 H 13 N3O4[M+H] + 278.0924, measured value: 278.0922.

[0226] Compound 20:

[0227]

[0228] (E)-11-(hydroxyimino)-3-ethyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one

[0229] 1 H NMR (400MHz, DMSO-d6) δ13.89(s,1H),8.93(s,1H),8.84(s,2H),8.21(dd,J=22 .4,8.2Hz,2H),7.82-7.64(m,2H),4.60(d,J=7.8Hz,2H),1.41(t,J=8.0Hz,3H).

[0230] HRMS(ESI): Theoretical value of m / z: C 15 H 13 N3O4[M+H] + 292.1081, measured value: 292.1078.

[0231] Example 2

[0232] 13.3 g of 2,2'-(1,4-dioxy-1,4,6,7-tetrahydronaphthyl-2,3-diyl)bis(isoindoline-1,3-dione) was dissolved in 200 mL of dichloromethane and 20 mL of methanol. Cyclopropylamine was added, and after reacting for 2 hours, the solvent was removed. 100 mL of water was added, and the mixture was stirred for 10 minutes, followed by filtration to obtain a red solid (10 g). 10 g of the solid was added directly to 150 mL of ethanol, and 8 mL of 80% hydrazine hydrate was added dropwise. After stirring at room temperature for half an hour, the organic phase was removed. 200 mL of water was added, and the mixture was stirred for 10 minutes. The mixture was filtered, washed with water until colorless, and dried under vacuum to obtain a blue solid 6.2 g of 2-amino-3-cyclopropyl-6,7-dihydronaphthyl-1,4-dione. 1 g of 2-amino-3-cyclopropyl-6,7-dihydronaphthyl-1,4-dione was refluxed in orthoformic acid (25 mL) for 2.5 h to remove the solvent. The white solid 1-cyclopropyl-6,7-dihydro-1H-naphthol [2,3-d]imidazol-4,9-dione (0.46 g) was separated by silica gel column chromatography. 0.21 g of 3-cyclopropylnaphthoquinone imidazole, 0.35 g of hydroxylamine hydrochloride, and 0.8 mL of pyridine were dissolved in 70 mL of ethanol and reacted at 100 °C for 36 h. After the reaction was complete, a solid precipitated from the solution. This solid was directly filtered and dried under vacuum to obtain a pale yellow solid (0.15 g).

[0233] Compound 21 can be prepared using the method of Example 2:

[0234] Compound 21:

[0235]

[0236] (E)-3-Cyclopropyl-9-(hydroxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0237] 1 H NMR (400MHz, DMSO-d6) δ13.00(s,1H),8.31(s,1H),8.25(dd,J=8.0,1.2Hz,1H),8.11(dd,J=8.0,1.4H z,1H),7.67(td,J=8.0,1.4Hz,1H),7.59(td,J=8.0,1.2Hz,1H),3.93-3.86(m,1H),1.13-1.03(m,4H).

[0238] 13 C NMR (101MHz, DMSO-d6) δ174.50,143.32,140.18,139.97,133.46,132.97,131.25,129.58,128.36,126.23,123.86,29.61,7.44.

[0239] HRMS(ESI): Theoretical value of m / z: C 14 H 11 N3O2[M+H] + 254.0924, measured value: 254.0927.

[0240] Example 3

[0241] 0.25 g of N-(3-chloro-1,4-dioxo-1,4,6,7-tetrahydronaphth-2-yl)acetamide was dissolved in 20 mL of tetrahydrofuran. Triethylamine and tert-butylamine were added sequentially to the reaction solution, and the mixture was refluxed under nitrogen protection for 26 hours. After cooling to room temperature, the solvent was removed, and 10 mL of ultrapure water was added. The mixture was stirred for half an hour to obtain N-(3-(tert-butylamino)-1,4-dioxo-1,4,6,7-tetrahydronaphth-2-yl)acetamide. This was dispersed in 85 mL of hydrazine hydrate (50%) and reacted at 80°C for two hours. The mixture was extracted with dichloromethane, and the organic phase was collected, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by silica gel column chromatography to obtain the product 2-amino-3-(tert-butylamino)-6,7-dihydronaphth-1,4-dione. 50 mL of triethyl orthoformate was added to 1.63 g of 2-amino-3-(tert-butylamino)-6,7-dihydronaphthyl-1,4-dione, and the mixture was refluxed for 3 hours. After cooling to room temperature and removing the solvent, the product 3-tert-butylnaphthylquinone imidazole was obtained by separation and purification using a silica gel column. 0.21 g of 3-tert-butylnaphthylquinone imidazole, 0.17 g of hydroxylamine hydrochloride, and 0.4 mL of pyridine were dissolved in 50 mL of ethanol and reacted at 110 °C for 24 hours. At the end of the reaction, a solid precipitated from the solution. This solid was directly filtered and dried under vacuum to obtain a pale yellow solid (0.16 g).

[0242] Compounds 22-32 can be prepared by adding amines with different substitutions using the method in Example 3. The raw materials and reaction conditions for other compounds remain unchanged, and the raw materials are all commercially available.

[0243] Compound 22:

[0244]

[0245] (E)-3-tert-butyl-9-(hydroxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0246] 1H NMR (400MHz, DMSO-d6) δ13.55(s,1H),8.49(s,1H),8.23(d,J=8.0Hz,1H),8.1 7(d,J=7.4Hz,1H),7.68(t,J=8.0Hz,1H),7.60(t,J=8.0Hz,1H),1.72(s,9H).

[0247] 13 C NMR (101MHz, DMSO-d6) δ173.70,142.87,142.71,140.17,132.99,132.43,131.66,129.80,127.11,127.08,123.26,59.59,29.32.

[0248] HRMS(ESI): Theoretical value of m / z: C 15 H 15 N3O2[M+H] + 270.1237, Measured value: 270.1241.

[0249] Compound 23:

[0250]

[0251] (E)-9-(hydroxyimino)-3-(pyrazin-2-ylmethyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0252] 1 H NMR (400MHz, DMSO-d6) δ13.06(s,1H),8.71(s,1H),8.59-8.41(m,3H),8.27(d,J=8.0Hz,1H),7.99(d,J=8.0Hz,1H),7.72-7.51(m,2H),5.87(s,2H).

[0253] 13 C NMR(101MHz,DMSO-d6)δ174.99,151.72,145.78,144.60,144.34,143.98,140 .12,139.84,133.89,133.16,130.80,129.55,126.79,126.08,124.01,49.11.

[0254] HRMS(ESI): Theoretical value of m / z: C 16 H 11 N5O2[M+H] + 306.0986, Measured value: 306.0985.

[0255] Compound 24:

[0256]

[0257] (E)-9-(hydroxyimino)-3-benzyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0258] 1 H NMR(400MHz,DMSO-d6)δ13.10(s,1H),8.47(s,1H),8.30(dd,J=8.0,1.2Hz,1H ),8.02(dd,J=8.0,1.4Hz,1H),7.69(td,J=8.0,1.4Hz,1H),7.63-7.48(m,6H).

[0259] 13 C NMR(101MHz,DMSO-d6)δ174.10,145.03,140.19,140.10,135.90,133.66, 133.07,131.24,129.59,129.36,129.31,127.14,126.57,126.27,123.91.

[0260] HRMS(ESI): Theoretical value of m / z: C 17 H 11 N3O2[M+H] + 290.0924, measured value: 290.0922.

[0261] Compound 25:

[0262]

[0263] (E)-9-(hydroxyimino)-3-(2,4,6-trimethylphenyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0264] 1 H NMR (400MHz, DMSO-d6) δ13.09(s,1H),8.35-8.26(m,2H),8.00-7.95(m,1H),7.73-7.65(m,1H),7.62-7.54(m,1H),7.03(s,2H),3.34(s,9H).

[0265] 13C NMR(101MHz,DMSO-d6)δ174.25,144.93,140.19,139.83,138.97,135.02,133.96 ,133.14,132.50,130.95,129.58,129.12,127.34,126.10,124.05,21.06,17.48.

[0266] HRMS(ESI): Theoretical value of m / z: C 20 H 17 N3O2[M+H] + 322.1394, measured value: 322.1392.

[0267] Compound 26:

[0268]

[0269] (E)-9-(hydroxyimino)-3-(2-fluorophenyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0270] 1 H NMR (400MHz, DMSO-d6) δ13.09(s,1H),8.50(s,1H),8.32(dd,J=8.0,1.2Hz,1H),8.01(dd,J=8.0, 1.4Hz,1H),7.75-7.65(m,2H),7.64-7.56(m,2H),7.51-7.44(m,1H),7.38(td,J=8.0,1.2Hz,1H).

[0271] 13 C NMR (101MHz, DMSO-d6) δ174.23, 158.18 (155.70, J = 248.0Hz), 145.23, 139.94 (139.68, J = 26.0Hz), 133.93, 133.26, 131.86 (131.78, J=8.0Hz),130.84,129.64,129.18,127.94,127.80,126.10,125.33(125.29,J=4.0Hz),124.21,124.10,116.75(116.55,J=20.0Hz).

[0272] HRMS(ESI): Theoretical value of m / z: C 17 H 10 FN3O2[M+H] + 308.0830, measured value: 308.0831.

[0273] Compound 27:

[0274]

[0275] (E)-9-(hydroxyimino)-3-(3-fluorophenyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0276] 1 H NMR (400MHz, DMSO-d6) δ13.08(s,1H),8.49(s,1H),8.30(dd,J=8.0,1.2Hz,1H),8.03(dd,J=8.0, 1.4Hz,1H),7.70(td,J=8.0,1.4Hz,1H),7.62-7.54(m,3H),7.48-7.43(m,1H),7.42-7.35(m,1H).

[0277] 13 C NMR(101MHz,DMSO-d6)δ174.15,163.26(160.83,J=243.0Hz),145.03,140.17(140.02,J=15.0Hz),137.30,137.19,133.70,133.11,131.17,13 0.96(130.87,J=9.0Hz),129.58,127.19,126.28,123.92,122.87(122. 84, J=3.0Hz), 116.42 (116.21, J=21.0Hz), 114.56 (114.31, J=25.0Hz).

[0278] HRMS(ESI): Theoretical value of m / z: C 17 H 10 FN3O2[M+H] + 308.0830, measured value: 308.0832.

[0279] Compound 28:

[0280]

[0281] (E)-9-(hydroxyimino)-3-(4-fluorophenyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0282] 1H NMR(400MHz,DMSO-d6)δ13.07(s,1H),8.45(s,1H),8.32-8.27(m,1H),8.02(d d,J=8.0,1.4Hz,1H),7.72-7.62(m,3H),7.61-7.55(m,1H),7.41-7.35(m,2H).

[0283] 13 C NMR(101MHz,DMSO-d6)δ174.18,163.67(161.22,J=245.0Hz),145.09,140.08,133.72,133.10,132.30(132.27,J= 3.0Hz), 131.19, 129.59, 128.95 (128.86, J = 9.0Hz), 127.28, 126.60, 126.24, 123.93, 116.22 (115.99, J = 23.0Hz).

[0284] HRMS(ESI): Theoretical value of m / z: C 17 H 10 FN3O2[M+H] + 308.0830, measured value: 308.0829.

[0285] Compound 29:

[0286]

[0287] (E)-9-(hydroxyimino)-3-(4-methoxyphenyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0288] 1 H NMR(400MHz,DMSO-d6)δ13.07(s,1H),8.40(s,1H),8.32-8.28(m,1H),8.02(dd,J=8.0,1.4Hz,1H),7.70 (td,J=8.0,1.4Hz,1H),7.59(td,J=8.0,1.2Hz,1H),7.51-7.47(m,2H),7.08-7.04(m,2H),3.82(s,3H).

[0289] 13C NMR(101MHz,DMSO-d6)δ174.10,159.95,159.53,145.06,140.16,133.63,133 .05,131.28,129.59,128.73,127.82,127.23,126.25,123.90,114.40,56.00.

[0290] HRMS(ESI): Theoretical value of m / z: C 18 H 13 FN3O3[M+H] + 320.1030, measured value: 320.1026.

[0291] Compound 30:

[0292]

[0293] (E)-9-(hydroxyimino)-3-(3-chloro-4-fluorophenyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0294] 1 H NMR (400MHz, DMSO-d6) δ13.13(s,1H),8.52(s,1H),8.30(dd,J=8.0,1.2Hz,1H),8.05-7.97(m,2H),7.72-7.64(m,2H),7.62-7.55(m,2H).

[0295] 13 C NMR(101MHz,DMSO-d6)δ174.25,158.99(156.52,J=247.0Hz),145.02,139.91,133.71,133.19,132.90(132.87,J=3.0Hz), 131.06,129.61,129.20,127.83,127.75,127.28,126.26,123.95,120.02(119.83,J=19.0Hz),117.46(117.24J=22.0Hz).

[0296] HRMS(ESI): Theoretical value of m / z: C 17 H9ClFN3O2[M+H] + 342.0440, measured value: 342.0438.

[0297] Compound 31:

[0298]

[0299] (E)-9-(hydroxyimino)-3-(3-bromo-4-fluorophenyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0300] 1 H NMR (400MHz, DMSO-d6) δ13.06(s,1H),8.47(s,1H),8.30(dd,J=8.0,1.2Hz,1H),8.10-8.00(m,2H),7.72–7.66(m,2H),7.61-7.53(m,2H).

[0301] 13 C NMR(101MHz,DMSO-d6)δ174.27,159.55,145.12,140.03(139.98,J=5.0Hz),133.77,133.16,133.15,131.83,13 1.11,129.59,128.45,128.37,127.34,126.25,123.96,117.20(116.96,J=24.0Hz),108.33(108.11,J=22.0Hz).

[0302] HRMS(ESI): Theoretical value of m / z: C 17 H9BrFN3O2[M+H] + 385.9935, measured value: 385.9930.

[0303] Compound 32:

[0304]

[0305] (E)-9-(hydroxyimino)-3-methyl-8-nitro-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0306] 1H NMR (400MHz, DMSO-d6) δ14.67(s,1H),9.66(s,1H),8.37(d,J=7.8Hz,1H),8.25(d,J=7.9Hz,1H),8.09(t,J=7.8Hz,1H),4.14(s,3H).

[0307] HRMS(ESI): Theoretical value of m / z: C 17 H9BrFN3O2[M+H] + 273.0619, measured value: 273.0620.

[0308] Example 4

[0309] 2,3,-Diamino-1,4-benzoquinone (20 g) was dissolved in 100 mL of acetic acid and refluxed for 6 hours. After cooling to room temperature, the solution was poured into an ice-water mixture, and ammonia was added to adjust the pH to 9-10. The mixture was filtered and dried under vacuum to obtain a yellow solid, 1,4-naphthoquinone imidazole (22 g). 1,4-naphthoquinone imidazole (0.3 g) and potassium hydroxide (0.15 g) were added sequentially to a dimethyl sulfoxide solution (3 mL). The mixture was stirred at 50°C for 30 minutes, and iodomethane (0.2 mL) was added. After reacting for 2 hours, water was added to precipitate the solid. The solid was filtered, washed with water, and dried under vacuum to obtain a yellow solid, 2-methyl-1,4-naphthoquinone imidazole (0.31 g). 2-Methylnaphthoquinone imidazole (0.2 g), hydroxylamine hydrochloride (0.28 g), and pyridine (0.7 mL) were dissolved in ethanol (70 mL) and reacted at 105 °C for 36 hours. After the reaction was completed, a solid precipitated in the solution. The solid was directly filtered and dried under vacuum to obtain a pale yellow solid (0.16 g).

[0310] 2,3,-Diamino-1,4-naphthoquinone (20 g) was dissolved in 100 mL of acetic acid and refluxed for 6 hours to obtain anthraquinone imidazole. Alternatively, compounds 33-41 could be prepared by adding substituted halogenated hydrocarbons, using the method of Example 4. The raw materials and reaction conditions for other compounds remained unchanged, and the raw materials were all commercially available.

[0311] Compound 33:

[0312]

[0313] (E)-9-(hydroxyimino)-2,3-dimethyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0314] 1 H NMR (400MHz, DMSO-d6) δ13.01 (s, 1H), 8.26 (d, J = 0.8Hz, 2H), 8.07 (dd, J = 8.0 ,4.0Hz,1H),7.72-7.64(m,1H),7.61-7.52(m,1H),4.00(s,3H),2.81(s,3H).

[0315] 13 C NMR (101MHz, DMSO-d6) δ175.27,145.22,140.18,139.62,133.71,133.06,131.04,129.58,127.17,126.12,123.92,34.14,20.1.

[0316] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H]+ 241.0851, Measured value: 241.0854.

[0317] Compound 34:

[0318]

[0319] (E)-3-Butyl-9-(hydroxyimino)-2-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0320] 1 H NMR (400MHz, DMSO-d6) δ13.14(s,1H),8.27(d,J=7.9Hz,1H),8.12(dd,J=7.8,1.5Hz,1H),7.73–7.65(m,1H) ,7.65–7.57(m,1H),4.41(d,J=15.1Hz,2H),1.73–1.65(m,2H),1.32(q,J=7.4Hz,2H),0.90(t,J=7.3Hz,3H).

[0321] Compound 35:

[0322]

[0323] (E)-11-(hydroxyimino)-2,3-dimethyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one

[0324] 1 H NMR (400MHz, DMSO-d6) δ13.09(s,1H),8.77(d,J=12.4Hz,2H),8.15(dd,J=26.4,7.8Hz,2H),7.64(d,J=20.0Hz,2H),4.03(s,3H),2.54(s,3H).

[0325] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 292.1081, Measured value: 292.1082.

[0326] Compound 36:

[0327]

[0328] (E)-3-ethyl-11-(hydroxyimino)-2-methyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one 1HNMR(400MHz,DMSO-d6)δ13.87(s,1H),8.84(s,2H),8.21(dd,J=22.4,8.2Hz,2H ),7.82-7.64(m,2H),4.60(d,J=7.8Hz,2H),2.79(s,3H),1.40(d,J=8.0Hz,3H).

[0329] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 306.1237, measured value: 306.1240.

[0330] Compound 37:

[0331]

[0332] (E)-3-Isobutyl-11-(hydroxyimino)-2-methyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one

[0333] 1 H NMR(400MHz,DMSO-d6)δ13.90(s,1H),8.84(s,2H),8.20(dd,J=15.0,8.4Hz,2H),7.81-7 .58(m,2H),4.41(d,J=7.0Hz,2H),2.78(s,3H),2.22-2.14(m,1H),0.95(d,J=6.8Hz,6H).

[0334] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 344.1550, Measured value: 344.1554.

[0335] Compound 38:

[0336]

[0337] (E)-11-(hydroxyimino)-2-methyl-3-(3-methyl-2-en-1-yl)-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one

[0338] 1H NMR(400MHz,DMSO-d6)δ13.44(s,1H),8.81(s,2H),8.24-8.13(m,2H),7.74-7.66(m ,2H),5.30-5.22(m,2H),5.14-5.10(m,1H),2.65(s,3H),1.84(s,3H),1.70(s,3H).

[0339] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 346.1550, Measured value: 346.1555.

[0340] Compound 39:

[0341]

[0342] (E)-2-(4-(hydroxyimino)-2-methyl-11-oxo-4,11-dihydro-1H-anthracene[2,3-d]imidazol-1-yl)acetonitrile

[0343] 1 H NMR (400MHz, DMSO-d6) δ13.46 (s, 1H), 8.69 (s, 2H), 8.26 (s, 2H), 7.76 (d, J = 6.4Hz, 2H), 5.70 (s, 2H), 2.59 (s, 3H).

[0344] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 317.1033, measured value: 317.1035.

[0345] Compound 40:

[0346]

[0347] (E)-3-benzyl-11-(hydroxyimino)-2-methyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one

[0348] 1 H NMR (400MHz, DMSO-d6) δ13.01 (s, 1H), 8.78 (d, J = 33.2Hz, 2H), 8.15 (dd, J = 16.8, 7.8Hz,2H),7.65(d,J=19.9Hz,2H),7.43-7.12(m,5H),5.83(s,2H),2.65(s,3H).

[0349] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 368.1394, measured value: 368.1395.

[0350] Compound 41:

[0351]

[0352] (E)-3-(4-fluorobenzyl)-11-(hydroxyimino)-2-methyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one

[0353] 1 H NMR (400MHz, DMSO-d6) δ13.50(s,1H),8.81(d,J=16.8Hz,2H),8.24–8.13(m,2H),7.75–7.60(m,2H),7.16(d,J=8.8Hz,4H),5.86(s,2H),2.62(s,3H).

[0354] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 386.1300, measured value: 386.1327.

[0355] Example 5

[0356] 4 g of 2,3,-diamino-1,4-benzoquinone was dissolved in 13 mL of dimethyl sulfoxide, and 2.12 mL of butyraldehyde was added. The mixture was reacted openly at 80°C for 13 hours. After cooling to room temperature, water was slowly added, and the precipitated solid was filtered and dried under vacuum to obtain a yellow solid, 0.15 g of 1,4-naphthoquinone imidazole. 0.3 g of 1,4-naphthoquinone imidazole and 0.15 g of potassium hydroxide were added sequentially to a 3 mL solution of dimethyl sulfoxide. The mixture was stirred at 50°C for 30 minutes, and 0.2 mL of iodobutane was added. After reacting for 2 hours, water was added, and the precipitated solid was filtered, washed with water, and dried under vacuum to obtain a yellow solid, 0.31 g of 2-methyl-1,4-naphthoquinone imidazole. 2-Methylnaphthoquinone imidazole (0.2 g), hydroxylamine hydrochloride (0.11 g), and pyridine (0.35 mL) were dissolved in ethanol (35 mL) and reacted at 105 °C for 36 hours. After the reaction was completed, a solid precipitated in the solution. The solid was directly filtered and dried under vacuum to obtain a pale yellow solid (0.15 g).

[0357] Compounds 42-59 can be prepared by dissolving 4 g of 2,3,-diamino-1,4-benzoquinone in 13 mL of dimethyl sulfoxide and reacting it with different aldehydes; or by dissolving 20 g of 2,3,-diamino-1,4-naphthoquinone in dimethyl sulfoxide and reacting it with different aldehydes; or by adding different substituted haloalkanes. The reactants and reaction conditions for other compounds remain unchanged, and all raw materials are commercially available.

[0358] Compound 42:

[0359]

[0360] (E)-3-Butyl-9-(hydroxyimino)-2-ethyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0361] 1 H NMR(400MHz, DMSO-d6)δ13.26(s,1H),8.25(d,J=7.9Hz,1H),8.10(d,J=8.0Hz,1H),7.75–7.65(m,1H),7.60(t,J=7.5Hz,1H),4.3 8(t,J=7.5Hz,2H),2.86(q,J=7.5Hz,2H),1.67(ddd,J=12.6,10.2,6.5Hz,2H),1.31(td,J=7.5,3.7Hz,5H),0.89(t,J=7.4Hz,3H).

[0362] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 298.1550, measured value: 298.1557.

[0363] Compound 43:

[0364]

[0365] (E)-3-Butyl-9-(hydroxyimino)-2-propyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0366] 1H NMR(400MHz,Chloroform-d)δ13.95(s,1H),8.42(d,J=7.8Hz,1H),8.28–8.21(m,1H),7.65(t,J=7.3Hz,1H),7.59–7.55(m,1H),4.46(t,J=7.6H z,2H),2.80(t,J=7.6Hz,2H),1.93(h,J=7.7Hz,2H),1.79(q,J=7.7Hz,2H),1.44(q,J=7.6Hz,2H),1.08(t,J=7.4Hz,3H),0.99(t,J=7.4Hz,3H).

[0367] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 312.1707, measured value: 312.1709.

[0368] Compound 44:

[0369]

[0370] (E)-2-(sec-butyl)-3-butyl-9-(hydroxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0371] 1 H NMR (400MHz, DMSO-d6) δ13.32(s,1H),8.26(d,J=8.0Hz,1H),8.13(d,J=7.8Hz ,1H),7.70(t,J=7.7Hz,1H),7.62(t,J=7.5Hz,1H),4.52-4.40(m,2H),3.08(q ,J=6.8Hz,1H),1.80(dt,J=14.0,7.4Hz,1H),1.67(q,J=7.3Hz,3H),1.39–1.3 2(m,2H),1.28(d,J=6.8Hz,3H),0.90(t,J=7.4Hz,3H),0.83(t,J=7.2Hz,3H).

[0372] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 326.1863, measured value: 326.1865.

[0373] Compound 45:

[0374]

[0375] (E)-3-Butyl-9-(hydroxyimino)-2-isobutyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one 1 HNMR(400MHz,Chloroform-d)δ13.91(s,1H),8.38(d,J=7.8Hz,1H),8.21(d,J=7.8Hz,1H),7.62(t,J=7.6Hz,1H),7.54(t,J=7.6Hz,1H),4 .44(t,J=7.8Hz,2H),2.68(d,J=7.0Hz,2H),2.32(dp,J=13.8,6.8Hz,1H),1.78(p,J=7.6Hz,2H),1.44(p,J=7.4Hz,2H),1.11–0.91(m,9H).

[0376] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 326.1863, measured value: 326.1862.

[0377] Compound 46:

[0378]

[0379] (E)-3-Butyl-9-(hydroxyimino)-2-(pentan-3-yl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0380] 1 H NMR(400MHz,Chloroform-d)δ14.05(s,1H),8.44(dd,J=8.0,1.2Hz,1H),8.29–8.20(m,1H),7.67(td,J=7.6,1.6Hz,1H),7.59(td,J=7.6,1.4H z,1H),4.57–4.46(m,2H),2.79(tt,J=8.4,5.6Hz,1H),1.92–1.80(m,6H),1.49(h,J=7.4Hz,2H),1.02(t,J=7.4Hz,3H),0.90(t,J=7.4Hz,6H).

[0381] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 340.2020, Measured value: 340.2025.

[0382] Compound 47:

[0383]

[0384] (E)-3-Butyl-9-(hydroxyimino)-2-tert-butyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one 1 HNMR(400MHz,Chloroform-d)δ14.09(s,1H),8.40(d,J=7.8Hz,1H),8.25(d,J=7.8Hz,1H),7.64(t,J=7.2Hz, 1H),7.56(t,J=7.8Hz,1H),4.62-4.49(m,2H),1.95-1.85(m,2H),1.60-1.53(m,11H),1.03(t,J=7.2Hz,3H).

[0385] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 326.1863, measured value: 326.1864.

[0386] Compound 48:

[0387]

[0388] (E)-3-Butyl-9-(hydroxyimino)-2-(2-(5-methylfuran-2-yl)ethyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0389] 1 H NMR(400MHz,Chloroform-d)δ13.87(s,1H),8.42(d,J=7.8Hz,1H),8.24(d,J =7.8Hz,1H),7.67–7.62(m,1H),7.60–7.53(m,1H),5.91(d,J=3.0Hz,1H),5.8 8–5.81(m,1H),4.38(t,J=7.6Hz,2H),3.24–3.07(m,3H),2.25(s,3H),1.90- 1.83(m,1H),1.78-1.67(m,2H),1.41(q,J=7.6Hz,2H),0.97(t,J=7.2Hz,3H).

[0390] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 378.1812, measured value: 378.1813.

[0391] Compound 49:

[0392]

[0393] (E)-3-Butyl-9-(hydroxyimino)-2-cyclobutyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one 1 HNMR(400MHz,Chloroform-d)δ14.08(s,1H),8.42(d,J=7.8Hz,1H),8.29–8.19(m, 1H),7.65(td,J=8.2,7.8,1.6Hz,1H),7.60–7.51(m,1H),4.44–4.28(m,2H),3.68( q,J=8.5Hz,1H),2.62–2.52(m,2H),2.44(q,J=8.9Hz,2H),2.17(q,J=9.5Hz,1H),2 .09-2.04(m,1H),1.76(p,J=7.8Hz,2H),1.48-1.35(m,2H),0.98(t,J=7.3Hz,3H).

[0394] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 324.1707, measured value: 324.1709.

[0395] Compound 50:

[0396]

[0397] (E)-3-Butyl-9-(hydroxyimino)-2-phenyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0398] 1 H NMR(400MHz,Chloroform-d)δ13.92(s,1H),8.46(d,J=7.8Hz,1H),8.29(d,J=7.8Hz,1H),7.69(d,J=7.4Hz,2 H),7.63-7.58(m,5H),4.58(t,J=7.8Hz,2H),1.86(q,J=7.6Hz,2H),1.37–1.31(m,2H),0.89(t,J=7.2Hz,3H).

[0399] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 346.1550, measured value: 346.1554.

[0400] Compound 51:

[0401]

[0402] (E)-3-Butyl-9-(hydroxyimino)-2-(4-isopropylphenyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0403] 1 H NMR(400MHz,Chloroform-d)δ13.96(s,1H),8.44(d,J=7.8Hz,1H),8.28(dd,J=78,1.6Hz,1H),7.93–7.54(m ,4H),7.52–7.31(m,2H),4.57(t,J=7.8Hz,2H),1.92-1.83(m,2H),1.42-1.25(m,8H),0.90(t,J=7.4Hz,3H).

[0404] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 388.2020, Measured value: 388.2024.

[0405] Compound 52:

[0406]

[0407] (E)-3-Butyl-9-(hydroxyimino)-2-(3,4,5-trimethoxyphenyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0408] 1 H NMR(400MHz,Chloroform-d)δ13.85(s,1H),8.45(d,J=7.8Hz,1H),8.29(d,J=7.8Hz,1H),7.68(t,J=8.0Hz,1H),7.60(t, J=7.4Hz,1H),6.88(s,2H),4.63–4.52(m,2H),3.94(s,9H),1.92-1.86(m,2H),1.40-1.34(m,2H),0.93(t,J=7.4Hz,3H).

[0409] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 436.1867, Measured value: 436.1868.

[0410] Compound 53:

[0411]

[0412] (E)-3-Butyl-2-(3-chloro-4-methoxyphenyl)-9-(hydroxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0413] 1 H NMR (400MHz, DMSO-d6) δ13.10(s,1H),8.30(d,J=8.0Hz,1H),8.16(d,J=7.6Hz,1H),7.81(s,1H),7.70(d,J=8.4Hz,2H),7.64(d,J= 7.6Hz,1H),7.34(d,J=8.5Hz,1H),4.48(t,J=8.4Hz,2H),3.94(s,3H),1.72-1.67(m,2H),1.19-1.12(m,2H),0.76(t,J=7.4Hz,3H).

[0414] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 410.1266, Measured value: 410.1266.

[0415] Compound 54:

[0416]

[0417] (E)-3-Butyl-9-(hydroxyimino)-2-naphthyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0418] 1 H NMR(400MHz,Chloroform-d)δ13.83(s,1H),8.50(dd,J=7.8,1.2Hz,1H),8.34(dd,J=7.8,1.6Hz,1H),8.12(dd,J=7.2,2.2Hz,1H),8.0 1(dd,J=8.0,1.8Hz,1H),7.78–7.51(m,7H),4.38(t,J=7.4Hz,2H),1.67(p,J=7.6Hz,2H),1.13(h,J=7.4Hz,2H),0.69(t,J=7.4Hz,3H).

[0419] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 396.1707, measured value: 396.1709.

[0420] Compound 55:

[0421]

[0422] (E)-3-Butyl-9-(hydroxyimino)-2-(trifluoromethyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0423] 1 H NMR(400MHz,Chloroform-d)δ12.85(s,1H),8.41(dd,J=8.0,1.2Hz,1H),8.24(dd,J=7.8,1.6Hz,1H),7.69(td,J=7.8,1.6H z,1H),7.59(td,J=7.6,1.2Hz,1H),4.72–4.54(m,2H),1.88(p,J=8.0Hz,2H),1.50(h,J=7.4Hz,2H),1.01(t,J=7.4Hz,3H).

[0424] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 338.1111, Measured value: 338.1115.

[0425] Compound 56:

[0426]

[0427] (E)-3-Butyl-9-(hydroxyimino)-2-(furan-2-yl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0428] 1 H NMR(400MHz,Chloroform-d)δ13.80(s,1H),8.43(d,J=8.0Hz,1H),8.28(d,J=7.8Hz,1H),7.66(d,J=10.2Hz,2H),7.61–7 .55(m,1H),7.24(d,J=4.8Hz,1H),4.96–4.89(m,2H),1.89(q,J=7.6Hz,2H),1.47(q,J=7.6Hz,2H),0.99(t,J=7.2Hz,3H).

[0429] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 336.1343, measured value: 336.1344.

[0430] Compound 57:

[0431]

[0432] (E)-3-Butyl-9-(hydroxyimino)-2-(thien-2-yl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0433] 1 H NMR(400MHz,Chloroform-d)δ13.78(s,1H),8.44(d,J=8.0Hz,1H),8.34–8.13(m,1H),7.70–7.52(m, 4H),7.24(s,1H),4.82–4.71(m,2H),1.95(p,J=8.2Hz,2H),1.53–1.45(m,2H),1.01(t,J=7.4Hz,3H).

[0434] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 352.1114, measured value: 352.1116.

[0435] Compound 58:

[0436]

[0437] (E)-2-Ethyl-11-(hydroxyimino)-3-methyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one 1 HNMR(400MHz,DMSO-d6)δ13.71(s,1H),8.60(d,J=5.6Hz,2H),8.21-8.15(m,2H ),7.71-7.65(m,2H),2.76(q,J=7.6Hz,2H),1.27(t,J=7.6Hz,2H),4.09(s,1H).

[0438] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 306.1237, Measured value: 306.1236.

[0439] Compound 59:

[0440]

[0441] (E)-2-(furan-2-yl)-11-(hydroxyimino)-3-methyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one

[0442] 1 H NMR (400MHz, DMSO-d6) δ13.85 (s, 1H), 8.69 (s, 2H), 8.27-8.22 (m, 2H), 7.95 (d, J = 1. 2Hz,1H),7.76-7.70(m,2H),7.35(d,J=3.4Hz,1H),6.75-6.70(m,1H),4.25(s,1H).

[0443] HRMS(ESI): Theoretical value of m / z: C 12 H9N3O2[M+H] + 344.1030, measured value: 344.1031.

[0444] Example 6

[0445] 2,3,-Diamino-1,4-benzoquinone (20 g) was dissolved in 100 mL of formic acid and refluxed for 6 hours. After cooling to room temperature, the solution was poured into an ice-water mixture. Ammonia was added to adjust the pH to 9-10. The mixture was filtered and dried under vacuum to obtain a yellow solid, 1,4-naphthoquinone imidazole (22 g). 1,4-naphthoquinone imidazole (0.3 g) and potassium hydroxide (0.15 g) were added sequentially to a dimethyl sulfoxide solution (3 mL). The mixture was stirred at 50°C for 30 minutes. Iodomethane (0.2 mL) was added, and after reacting for 2 hours, water was added to precipitate the solid. The solid was filtered, washed with water, and dried under vacuum to obtain a yellow solid, 2-methyl-1,4-naphthoquinone imidazole (0.31 g). 2-Methylnaphthoquinone imidazole (0.2 g), methoxyamine hydrochloride (0.1 g), and pyridine (0.08 mL) were dissolved in ethanol (30 mL) and reacted at 125 °C for 12 hours. After the reaction was completed, a solid precipitated in the solution. The solid was directly filtered and dried under vacuum to obtain a pale yellow solid (0.15 g).

[0446] 2,3,-Diamino-1,4-naphthoquinone (20 g) was dissolved in 100 mL of formic acid and refluxed for 6 hours to obtain anthraquinone imidazole. Compounds 60-77 could be prepared using different substituted aminooxyhydrochlorides according to the method of Example 6. The raw materials and reaction conditions for other compounds remained unchanged, and all raw materials were commercially available.

[0447] Compound 60:

[0448]

[0449] (E) and (Z)-9-(methoxyimino)-3-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0450] 1H NMR (400MHz, DMSO-d6) δ8.99 (dd, J=8.0, 1.2Hz, 1H), 8.31-8.20 (m, 4H), 8.16-8.0 7(m,2H),7.82-7.60(m,5H),4.24(s,3H),4.20(s,4H),4.03(s,4H),3.99(s,3H).

[0451] 13 C NMR (101MHz, DMSO) δ175.40,174.52,145.91,145.85,145.58,140.34,139.95,139.03,133.69,133.20,133.12,132 .39,131.62,131.20,131.09,129.94,128.10,128.03,127.04,126.43,126.16,124.33,64.73,64.47,34.20,33.92.

[0452] HRMS(ESI): Theoretical value of m / z: C 13 H 11 N3O2[M+H] + 242.0924, measured value: 242.0928.

[0453] Compound 61:

[0454]

[0455] (E) and (Z)-9-(ethoxyimino)-3-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one 1 HNMR(400MHz, DMSO-d6)δ9.04(dd,J=8.0,1.2Hz,1H),8.30(dd,J=8.0,1.2Hz,2H),8.26-8.20(m,3H),8.14-8.07(m,3H),7.79(td, J=8.0,1.6Hz,1H),7.75-7.68(m,3H),7.63(td,J=8.0,1.2Hz,2H),4.53-4.42(m,6H),4.04(s,6H),4.00(s,3H),1.46-1.32(m,9H).

[0456] 13C NMR (101MHz, DMSO) δ175.42,174.53,146.10,145.90,145.64,140.16,139.75,139.33,133.66,133.50,133.04,132.38,13 1.51,131.07,129.79,128.08,128.04,127.00,126.37,126.10,124.33,124.09,72.72,72.20,34.16,33.90,15.29,15.04.

[0457] HRMS(ESI): Theoretical value of m / z: C 14 H 13 N3O2[M+H] + 256.1081, Measured value: 256.1085.

[0458] Compound 62:

[0459]

[0460] (E) and (Z)-9-(benzyloxyimino)-3-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0461] 1 H NMR (400MHz, DMSO-d6) δ8.30-8.22(m,2H),8.11(dd,J=8.0,1.2Hz,1H),7.71(td,J=8.0,1.6Hz,1 H),7.64(td,J=8.0,1.2Hz,1H),7.55-7.49(m,2H),7.45-7.31(m,3H),5.50(s,2H),4.03(s,3H).

[0462] Compound 63:

[0463]

[0464] (E) and (Z)-9-(isopropoxyimino)-3-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0465] 1H NMR(400MHz, DMSO-d6)δ9.07(dd,J=8.0,1.2Hz,1H),8.33(dd,J=8.0,1.2Hz,1H),8.28-8.21(m,2H),8.16-8.10(m,2H),7.80(td,J=8.0,1.6H z,1H),7.72(td,J=8.0,1.4Hz,2H),7.63(td,J=8.0,1.2Hz,1H),4.72-4.60(m,2H),4.04(s,3H),4.00(s,3H),1.43(dd,J=12.0,8.0Hz,12H).

[0466] 13 C NMR (101MHz, DMSO) δ175.44,174.53,146.27,145.91,145.69,139.80,139.47,139.28,133.77,133.66,133.03,132.39,13 1.42,131.07,130.99,129.68,128.14,128.00,127.00,126.32,126.07,124.33,79.35,78.63,34.16,33.91,22.10,21.97.

[0467] HRMS(ESI): Theoretical value of m / z: C 15 H 15 N3O2[M+H] + 270.1237, Measured value: 270.1238.

[0468] Compound 64:

[0469]

[0470] (E) and (Z)-9-(butoxyimino)-3-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0471] 1H NMR(400MHz, DMSO-d6)δ9.03(dd,J=8.0,1.2Hz,2H),8.30(dd,J=8.0,1.2Hz,1H),8.28-8.21(m,4H),8.14(s,3H),7.87-7.78(m,3H),7.76-7.6 9(m,3H),7.64(td,J=8.0,1.2Hz,1H),4.48-4.38(m,7H),4.04(s,3H), 4.00(s,7H),1.85-1.72(m,7H),1.53-1.39(m,7H),1.00-0.92(m,10H).

[0472] 13 C NMR (101MHz, DMSO) δ175.45,174.54,146.12,145.96,145.75,140.23,139.79,139.45,133.74,133.53,133.09,132.41,131.42,131.14, 129.82,128.11,128.07,127.07,126.92,126.40,126.14,124.34,76 .88,76.36,34.17,33.92,31.53,31.20,19.23,19.08,14.25,14.23.

[0473] HRMS(ESI): Theoretical value of m / z: C 16 H 17 N3O2[M+H] + 284.1394, Measured value: 284.1398.

[0474] Compound 65:

[0475]

[0476] (E) and (Z)-9-(isobutoxyimino)-3-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0477] 1H NMR (400MHz, DMSO-d6) δ9.04(dd,J=8.1,1.2Hz,1H),8.33-8.23(m,4H),8.15-8.09(m,3H),7.82(td,J=8.0,1.6Hz,1H),7.75-7.69(m,2H),7. 64(td,J=8.0,1.2Hz,2H),4.25(d,J=8.0Hz,2H),4.21(d,J=8.0Hz,3H),4.04(s,5H),4.00(s,3H),2.20-2.09(m,3H),1.01(t,J=6.0Hz,16H).

[0478] 13 C NMR (101MHz, DMSO) δ175.44,174.52,146.10,145.95,145.77,140.24,139.84,139.48,133.73,133.50,133.07,132.42,131.3 4,131.14,131.10,129.80,128.08,127.09,126.40,126.13,124.32,83.43,82.87,34.16,33.92,28.50,28.21,19.45,19.42.

[0479] HRMS(ESI): Theoretical value of m / z: C 16 H 17 N3O2[M+H] + 284.1394, measured value: 284.1397.

[0480] Compound 66:

[0481]

[0482] (E) and (Z)-9-(tert-butoxyimino)-3-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0483] 1 H NMR (400MHz, DMSO-d6) δ9.10 (dd, J=8.0, 1.2Hz, 1H), 8.38 (dd, J=8.0, 1.2Hz, 1H), 8.27-8.21 (m, 2H),8.15-8.10(m,2H),7.83-7.60(m,5H),4.05(s,3H),4.01(s,4H),1.50(s,12H),1.48(s,9H).

[0484] 13C NMR (101MHz, DMSO) δ175.47,174.56,146.58,145.91,145.70,139.61,139.39,138.81,134.17,133.61,133.01,132.40,13 1.32,131.05,130.83,129.52,128.22,127.95,126.95,126.23,126.02,124.29,82.90,82.08,34.15,33.90,28.02,27.74.

[0485] HRMS(ESI): Theoretical value of m / z: C 16 H 17 N3O2[M+H] + 284.1394, measured value: 284.1393.

[0486] Compound 67:

[0487]

[0488] (E) and (Z)-9-((cyclopropoxy)imino)-3-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0489] 1 H NMR(400MHz, DMSO-d6)δ9.10(dd,J=8.0,1.2Hz,1H),8.33-8.24(m,4H),8.16-8.09(m,3H),7.84-7.77(m,1H),7.75-7.70(m,2H),7 .64(td,J=8.0,1.2Hz,2H),4.32-4.24(m,5H),4.04(s,5H),4.00(s,3H),1.36-1.26(m,3H),0.65-0.55(m,6H),0.48-0.35(m,5H).

[0490] 13 C NMR (101MHz, DMSO) δ175.45,174.54,146.15,145.95,145.72,140.08,139.62,139.41,133.69,133.58,133.07,132.40,131.50, 131.11,131.09,129.77,128.17,128.06,127.04,126.39,126.12,124.35,81.62,80.98,34.16,33.91,11.04,10.65,3.64,3.59.

[0491] HRMS(ESI): Theoretical value of m / z: C 16 H 15 N3O2[M+H] + 282.1237, measured value: 282.1238.

[0492] Compound 68:

[0493]

[0494] (E) and (Z)-9-((allyloxy)imino)-3-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0495] 1 H NMR(400MHz, DMSO-d6)δ9.03(dd,J=8.0,1.2Hz,1H),8.30-8.21(m,6H),8.15-8.08(m,4H),7.80(td,J=8.0,1.6Hz,1H),7.77-7.65(m,4 H),7.64(td,J=8.0,1.2Hz,3H),6.22-6.08(m,4H),5.55-5.40(m,4H),5.36-5.27(m,4H),5.00-4.92(m,7H),4.04(s,8H),3.99(s,3H).

[0496] 13 C NMR (101MHz, DMSO) δ175.43,174.51,145.94,145.72,140.65,140.24,139.31,135.14,134.58,134.13,133.71,133.34,133.09,132 .42,131.59,131.22,131.12,129.93,128.15,128.05,127.08,126.48,126.15,124.37,119.04,118.54,77.72,77.22,34.16,33.92.

[0497] HRMS(ESI): Theoretical value of m / z: C 15 H 13 N3O2[M+H] + 268.1081, Measured value: 268.1083.

[0498] Compound 69:

[0499]

[0500] (E) and (Z)-3-methyl-9-(((4-methoxybenzyl)oxy)imino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0501] 1 H NMR(400MHz,DMSO-d6)δ9.05-8.98(m,1H),8.34-8.27(m,3H),8.27-8.20(m,4H),8.15-8.09(m,4H),7.76-7.61(m,8H) ,7.49-7.43(m,8H),6.99-6.93(m,8H),5.44(s,2H),5.41(s,6H),4.03(s,9H),3.99(s,3H),3.76(s,3H),3.75(s,9H).

[0502] 13 C NMR(101MHz,DMSO)δ175.43,174.52,159.81,159.60,145.98,145.75,140.5 2,140.16,139.34,133.72,133.41,133.13,132.42,131.50,131.19,131.13 ,130.65,130.54,129.93,129.82,129.17,128.15,128.09,127.08,126.48,126.16,124.38,114.40,114.24,78.57,78.04,55.58,55.55,34.16,33.92.

[0503] HRMS(ESI): Theoretical value of m / z: C 20 H 17 N3O3[M+H] + 348.1343, measured value: 348.1339.

[0504] Compound 70:

[0505]

[0506] (E) and (Z)-3-methyl-9-(((4-chlorobenzyl)oxy)imino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0507] 1H NMR(400MHz,DMSO-d6)δ9.03(dd,J=8.0,1.2Hz,1H),8.28-8.22(m,5H),8.14-8.08(m,3H), 7.82-7.60(m,7H),7.57-7.43(m,13H),5.51(s,2H),5.49(s,4H),4.03(s,6H),3.99(s,3H).

[0508] 13 C NMR(101MHz,DMSO)δ175.42,174.50,145.97,145.80,140.99,140.68,139 .26,137.10,136.54,133.77,133.30,133.21,133.16,132.98,132.47,131 .63,131.33,131.31,131.16,130.52,130.32,130.06,129.03,128.87,128 .27,128.03,127.13,126.55,126.20,124.40,77.67,77.17,34.17,33.92.

[0509] HRMS(ESI): Theoretical value of m / z: C 19 H 14 ClN3O2[M+H] + 352.0847, measured value: 352.0843.

[0510] Compound 71:

[0511]

[0512] (E) and (Z)-3-methyl-9-(((4-trifluoromethylbenzyl)oxy)imino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0513] yellow solid,100mg,% yield,mp136-138℃.

[0514] 1 H NMR (400MHz, DMSO-d6) δ9.07 (dd, J=8.0, 1.2Hz, 1H), 8.28-8.21 (m, 4H), 8.14-8.0 7(m,3H),7.82-7.60(m,17H),5.63(s,2H),5.60(s,3H),4.04(s,5H),3.99(s,3H).

[0515] 13C NMR(101MHz,DMSO)δ175.40,174.48,145.95,145.80,145.73,142.98,142.48,141.24,14 0.95,139.23,133.78,133.15,133.11,132.48,131.70,131.35,131.16,130.09,128.94, 128.74,128.62,128.31,128.00,127.13,126.57,126.19,126.07,125.95,125.91,125.87,125.83,125.79,125.76,125.72,125.68,124.39,123.37,77.49,77.04,34.17,33.90.

[0516] HRMS(ESI): Theoretical value of m / z: C 20 H 14 F3N3O2[M+H] + 386.1111, Measured value: 386.1107.

[0517] Compound 72:

[0518]

[0519] (E) and (Z)-3-methyl-9-(((4-fluorobenzyl)oxy)imino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0520] 1 H NMR (400MHz, DMSO-d6) δ9.03 (dd, J=8.0, 1.4Hz, 1H), 8.33-8.20 (m, 5H), 8.18-8.09 (m, 3H), 7.79-7.53(m,12H),7.30-7.17(m,7H),5.50(s,2H),5.48(s,3H),4.03(s,5H),3.99(s,3H).

[0521] 13C NMR (101MHz, DMSO) δ175.43,174.51,163.71,163.54,161.12,145.98,145.88,145.79,140 .85,140.53,139.28,134.26,134.23,133.76,133.72,133.69,133.27,133.16,132.46,131 .59,131.28,131.16,131.06,130.98,130.84,130.76,130.03,129.51,128.24,128.04,127.12,126.54,126.19,124.40,115.96,115.79,115.75,115.57,77.83,77.35,34.17,33.92.

[0522] HRMS(ESI): Theoretical value of m / z: C 19 H 14 FN3O2[M+H] + 336.1143, measured value: 336.1140.

[0523] Compound 73:

[0524]

[0525] (E) and (Z)-3-methyl-9-(((perfluorobenzyl)oxy)imino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0526] yellow solid,100mg,% yield,mp224-226℃.

[0527] 1 H NMR(400MHz,DMSO-d6)δ8.92(dd,J=8.0,1.2Hz,1H),8.26-8.07(m,7H),7.83-7.71(m, 4H),7.65(td,J=8.0,1.2Hz,2H),5.61(s,2H),5.53(s,3H),4.02(s,5H),3.98(s,3H).

[0528] 13C NMR (101MHz, DMSO) δ175.39,174.49,146.06,145.82,145.43,144.63,141.75,141.24,138.94,133.86,133.81,133.32,132.90,132.55,131 .67,131.67,131.59,131.23,130.34,130.11,128.49,128.46,127.93 ,127.87,127.20,126.26,124.69,124.25,65.48,64.75,34.17,33.93.

[0529] HRMS(ESI): Theoretical value of m / z: C 19 H 10 F5N3O2[M+H] + 408.0766, Measured value: 408.0767.

[0530] Compound 74:

[0531]

[0532] (E) and (Z)-3-methyl-9-(((4-nitrobenzyl)oxy)imino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0533] 1 H NMR(400MHz,DMSO-d6)δ9.09(dd,J=8.0,1.2Hz,1H),8.31-8.17(m,14H),8.13-8.09(m,3 H),7.84-7.62(m,15H),5.67(s,2H),5.65(s,5H),4.08-4.02(m,8H),3.99-3.97(m,3H).

[0534] 13 C NMR(101MHz,DMSO)δ175.42,174.50,147.64,147.47,146.09,145.97,145 .85,145.66,145.55,141.45,141.20,139.20,133.85,133.21,133.02,132 .51,131.79,131.46,131.18,130.20,129.18,128.95,128.37,127.98,127 .19,126.62,126.24,124.43,124.15,124.03,77.09,76.65,34.20,33.93.

[0535] HRMS(ESI): Theoretical value of m / z: C 19 H 14 N4O4[M+H] + 363.1088, measured value: 363.1084.

[0536] Compound 75:

[0537]

[0538] (E) and (Z)-11-(benzyloxyimino)-3-methyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one

[0539] 1 H NMR(400MHz,DMSO-d6)δ9.67(s,1H),8.79(d,J=6.8Hz,2H),8.73(s,1H),8.27(s,1H),8.23–8.08(m,6H),8. 00–7.95(m,1H),7.73–7.55(m,11H),7.46–7.33(m,8H),5.57(s,2H),5.53(s,3H),4.06(s,5H),4.01(s,3H).

[0540] HRMS(ESI): Theoretical value of m / z: C 19 H 14 N4O4[M+H] + 368.1394, measured value: 368.1397.

[0541] Compound 76:

[0542]

[0543] (E) and (Z)-11-(butoxyimino)-3-methyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one

[0544] 1H NMR(400MHz, DMSO-d6)δ9.58(s,1H),8.75(d,J=2.1Hz,2H),8.69(s,1H),8.24(s,1H),8.21–8.09(m,5H),8.02–7.98(m,1H),7.7 3–7.59(m,5H),4.45(dt,J=20.6,6.6Hz,5H),4.05(s,3H),4.01(s,4H),1.90-1.75(m,5H),1.57-1.45(m,5H),1.05-0.96(m,7H).

[0545] HRMS(ESI): Theoretical value of m / z: C 19 H 14 N4O4[M+H] + 334.2210, Measured value: 334.2214.

[0546] Compound 77:

[0547]

[0548] (E) and (Z)-11-(tert-butoxyimino)-3-methyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one

[0549] 1 H NMR(400MHz,DMSO-d6)δ9.70(s,1H),8.87(s,1H),8.81(s,1H),8.74(s,1H),8.28–8.13(m,5H ),8.07–8.02(m,1H),7.75–7.60(m,4H),4.08(s,3H),4.04(s,3H),1.55(s,9H),1.52(s,9H).

[0550] HRMS(ESI): Theoretical value of m / z: C 19 H 14 N4O4[M+H] + 334.2210, measured value: 334.2213.

[0551] Example 7

[0552] 2,3,-Diamino-1,4-benzoquinone (20 g) was dissolved in 100 mL of formic acid and refluxed for 6 hours. After cooling to room temperature, the solution was poured into an ice-water mixture. Ammonia was added to adjust the pH to 9-10. The mixture was filtered and dried under vacuum to obtain a yellow solid, 1,4-naphthoquinone imidazole (22 g). 1,4-naphthoquinone imidazole (0.3 g) and potassium hydroxide (0.15 g) were added sequentially to a dimethyl sulfoxide solution (3 mL). The mixture was stirred at 50°C for 30 minutes. Iodomethane (0.2 mL) was added, and after reacting for 2 hours, water was added to precipitate the solid. The solid was filtered, washed with water, and dried under vacuum to obtain a yellow solid, 2-methyl-1,4-naphthoquinone imidazole (0.31 g). 0.2 g of 2-methylnaphthoquinone imidazole, 0.3 g of hydroxylamine hydrochloride, and 0.7 mL of pyridine were dissolved in 70 mL of ethanol and reacted at 105 °C for 36 h. Upon completion of the reaction, a solid precipitated from the solution. This solid was directly filtered and dried under vacuum to obtain a pale yellow solid (E)-9-(hydroxyimino)-3-methyl-3,6,7,9-tetrahydro-4H-naphthol[2,3-d]imidazol-4-one (0.15 g). 106 mg of the oxime product was added to 2 mL of dimethyl sulfoxide solution, followed by 56 μL of bromomethyl ethyl ether and 104 mg of potassium hydroxide. The reaction was carried out at room temperature for two h. The reaction was quenched with water after complete reaction, extracted with dichloromethane, washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated, and separated by silica gel column chromatography.

[0553] Compounds 78-82 can be prepared by reacting the oxime product with substituted alkyl halides using the method of Example 7. The raw materials and reaction conditions for other compounds remain unchanged, and the raw materials are all commercially available.

[0554] Compound 78:

[0555]

[0556] (E)-9-((2-methoxyethoxy)imino)-3-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0557] 1 H NMR(400MHz,DMSO-d6)δ8.34-8.24(m,2H),8.16-8.09(m,1H),7.76-7.70(m,1H),7.65(td, J=8.0,1.2Hz,1H),4.53(t,J=4.0Hz,2H),4.04(s,3H),3.76(t,J=4.0Hz,2H),3.32(s,3H).

[0558] 13C NMR (101MHz, DMSO) δ175.46,145.74,140.04,139.32,133.40,133.14,131.13,129.95,128.15,126.17,124.43,76.07,70.75,58.76,34.18.

[0559] HRMS(ESI): Theoretical value of m / z: C 15 H 15 N3O3[M+H] + 286.1186, Measured value: 286.1188.

[0560] Compound 79:

[0561]

[0562] (E) and (Z)-9-((2-(benzyloxy)ethoxy)imino)-3-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0563] 1 H NMR(400MHz,DMSO-d6)δ8.30-8.25(m,2H),8.15-8.10(m,1H),7.75-7.61(m,2H),7.3 8-7.31(m,2H),7.30-7.21(m,3H),4.63-4.54(m,4H),4.04(s,3H),3.89-3.82(m,2H).

[0564] 13 C NMR(101MHz,DMSO-d6)δ175.45,145.72,140.12,139.36,138.95,133.39,133.08,131.1 3,129.92,128.60,128.15,127.86,127.74,126.14,124.43,76.28,72.40,68.47,34.18.

[0565] HRMS(ESI): Theoretical value of m / z: C 21 H 19 N3O3[M+H] + 362.1499, measured value: 362.1495.

[0566] Compound 80:

[0567]

[0568] (E)-9-((2-(2-methoxyethoxy)ethoxy)imino)-3-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0569] 1 H NMR (400MHz, DMSO-d6) δ8.31(dd,J=8.0,1.2Hz,1H),8.24(s,1H),8.13(dd,J=8.0,1.6Hz,1H),7.72(td,J=8.0,1.6Hz,1H),7.6 5(td,J=8.0,1.4Hz,1H),4.55-4.49(m,2H),4.04(s,3H),3.86-3.80(m,2H),3.64-3.59(m,2H),3.46-3.42(m,2H),3.22(s,3H).

[0570] 13 C NMR (101MHz, DMSO-d6) δ175.45,145.72,140.07,139.31,133.40,133.13,131. 13,129.95,128.15,126.16,124.45,76.25,71.78,70.26,69.26,58.52,34.18.

[0571] HRMS(ESI): Theoretical value of m / z: C 17 H 19 N3O4[M+H] + 330.1448, measured value: 330.1447.

[0572] Compound 81:

[0573]

[0574] (E) and (Z)-9-((2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)imino)-3-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0575] 1H NMR (400MHz, DMSO-d6) δ8.30(dd,J=8.0,1.2Hz,1H),8.23(s,1H),8.14-8.10(m,1H),7.74-7.69(m,1H),7.65(td,J=8.0,1.2Hz ,1H),4.55-4.51(m,2H),4.04(s,3H),3.87-3.82(m,2H),3.65-3.59(m,2H),3.54-3.47(m,4H),3.39-3.35(m,2H),3.19(s,3H).

[0576] 13 C NMR(101MHz,DMSO-d6)δ175.44,145.70,140.04,139.29,133.39,133.11,131.10,129 .93,128.12,126.14,124.43,76.23,71.70,70.48,70.24,70.03,69.26,58.46,34.16.

[0577] HRMS(ESI): Theoretical value of m / z: C 19 H 23 N3O5[M+H] + 374.1710, measured value: 374.1709.

[0578] Compound 82:

[0579]

[0580] (E)-9-((3-aminopropoxy)imino)-3-methyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0581] 1 H NMR(400MHz,DMSO-d6)δ8.30-8.25(m,2H),8.15-8.10(m,1H),7.75-7.61(m,2H ), 4.04 (s, 3H), 3.51 (t, J = 8.0Hz, 2H), 2.68 (t, J = 8.0Hz, 2H), 1.79-1.70 (m, 2H).

[0582] HRMS(ESI): Theoretical value of m / z: C 19 H 23 N3O5[M+H] + 285.1346, Measured value: 285.1347.

[0583] Example 8

[0584] 2,3,-Diamino-1,4-benzoquinone (20 g) was dissolved in 100 mL of formic acid and refluxed for 6 hours. After cooling to room temperature, the solution was poured into an ice-water mixture. Ammonia was added to adjust the pH to 9-10. The mixture was filtered and dried under vacuum to obtain a yellow solid, 1,4-naphthoquinone imidazole (22 g). 1,4-naphthoquinone imidazole (0.3 g) and potassium hydroxide (0.15 g) were added sequentially to a dimethyl sulfoxide solution (3 mL). The mixture was stirred at 50°C for 30 minutes. Iodobutane (0.18 mL) was added, and after reacting for 5 hours, water was added to precipitate the solid. The solid was filtered, washed with water, and dried under vacuum to obtain a yellow solid, 2-butyl-1,4-naphthoquinone imidazole (0.31 g). 2-Butyronitrile imidazole (0.21 g), methoxyamine hydrochloride (0.3 g), and pyridine (0.7 mL) were dissolved in ethanol (70 mL) and reacted at 105 °C for 36 hours. After the reaction was completed, the mixture was concentrated and separated by silica gel column chromatography to obtain a pale yellow product (0.18 g).

[0585] 2,3,-Diamino-1,4-naphthoquinone (20 g) was dissolved in 100 mL of formic acid and refluxed for 6 hours to obtain anthraquinone imidazole. Compounds 83-86 can be prepared by using different substituted haloalkanes or different substituted aminooxyhydrochlorides, following the method of Example 8. The raw materials and reaction conditions for other compounds remain unchanged, and the raw materials are all commercially available.

[0586] Compound 83:

[0587]

[0588] (E) and (Z)-3-butyl-9-(methoxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0589] 1 H NMR (400MHz, DMSO-d6) δ9.00(dd,J=8.0,1.2Hz,1H),8.34-8.21(m,4H),8.13(dd,J=8.0,1.4Hz,1H),7.82-7.62(m,4H),4.46( t,J=7.2Hz,2H),4.40(t,J=7.0Hz,2H),4.24(s,3H),4.21(s,3H),1.84-1.72(m,4H),1.37-1.18(m,4H),0.91(t,J=8.0Hz,6H).

[0590] 13C NMR (101MHz, DMSO) δ175.14,174.26,146.33,145.50,145.23,140.43,140.02,139.65,133.69,133.17,133.10,132.43,131.59,1 31.20,131.15,129.93,127.94,127.51,127.14,126.25,125.85,124.31,64.75,64.49,46.53,46.39,32.75,19.52,19.50,13.88.

[0591] HRMS(ESI): Theoretical value of m / z: C 16 H 17 N3O2[M+H] + 284.1394, Measured value: 284.1394.

[0592] Compound 84:

[0593]

[0594] (E) and (Z)-3-butyl-9-(ethoxyimino)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0595] 1 H NMR(400MHz,DMSO-d6)δ9.06(d,J=8.0Hz,1H),8.37-8.19(m,6H),8.14(d,J=8.0Hz,2H),7.83-7.61(m,6 H),4.55-4.36(m,11H),1.82-1.72(m,6H),1.46-1.38(m,9H),1.35-1.20(m,7H),0.91(t,J=8.0Hz,9H).

[0596] 13 C NMR (101MHz, DMSO) δ175.16,174.27,146.52,145.50,145.27,140.23,139.77,133.69,133.43,133.07,132.42,131.50,131.13, 129.82,128.00,127.43,127.13,126.21,125.79,124.31,72.74,72.25,46.52,46.38,32.78,19.52,19.50,15.29,15.06,13.89.

[0597] HRMS(ESI): Theoretical value of m / z: C17 H 19 N3O2[M+H] + 298.1550, measured value: 298.1549.

[0598] Compound 85:

[0599]

[0600] (E) and (Z)-9-((benzyloxy)imino)-3-butyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0601] 1 H NMR (400MHz, DMSO-d6) δ9.06 (dd, J=8.0, 1.2Hz, 1H), 8.36-8.24 (m, 6H), 8.22 (s, 1H), 8.13 (dd,J=8.0,1.6Hz,2H),7.81-7.69(m,4H),7.65(dd,J=8.0,1.4Hz,2H),7.63-7.59(m,1H) ,7.56-7.49(m,6H),7.45-7.31(m,16H),5.53(s,2H),5.50(s,5H),4.45(t,J=7.2Hz,5H), 4.39(t,J=7.1Hz,2H),1.82-1.72(m,7H),1.34-1.22(m,7H),0.90(td,J=8.0,1.0Hz,11H).

[0602] Compound 86:

[0603]

[0604] (E) and (Z)-11-((methoxy)imino)-3-(2-(2-methoxyethoxy)ethyl)-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one

[0605] 1 H NMR(400MHz, DMSO-d6)δ9.55(s,2H),8.74(d,J=9.3Hz,3H),8.69(s,1H),8.63(s,1H),8.59(s,1H),8.25–8.04(m,12H),7.75– 7.63(m,7H),4.58(dq,J=16.0,5.2Hz,7H),4.25(s,5H),4.18(s,3H),3.83-3.75(m,7H),3.55-3.10(m,7H),3.14–3.12(m,8H).

[0606] HRMS(ESI): Theoretical value of m / z: C 17 H 19 N3O2[M+H] + 380.1605, measured value: 380.1609.

[0607] Example 9

[0608] 2,3,-Diamino-1,4-benzoquinone (20 g) was dissolved in 100 mL of acetic acid and refluxed for 6 hours. After cooling to room temperature, the solution was poured into an ice-water mixture, and ammonia was added to adjust the pH to 9-10. The mixture was filtered and dried under vacuum to obtain a yellow solid, 1,4-naphthoquinone imidazole (22 g). 1,4-naphthoquinone imidazole (0.3 g) and potassium hydroxide (0.15 g) were added sequentially to a dimethyl sulfoxide solution (3 mL). The mixture was stirred at 50°C for 30 minutes. Iodobutane (0.18 mL) was added, and after reacting for 5 hours, water was added to precipitate the solid. The solid was filtered, washed with water, and dried under vacuum to obtain a yellow solid, 2-butyl-1,4-naphthoquinone imidazole (0.31 g). 2-Butyronitrile imidazole (0.21 g), methoxyamine hydrochloride (0.3 g), and pyridine (0.7 mL) were dissolved in ethanol (70 mL) and reacted at 105 °C for 36 hours. After the reaction was completed, the mixture was concentrated and separated by silica gel column chromatography to obtain a pale yellow product (0.16 g).

[0609] 2,3,-Diamino-1,4-naphthoquinone (20 g) was dissolved in 100 mL of formic acid and refluxed for 6 hours to obtain anthraquinone imidazole. Compounds 87-88 could be prepared using the method of Example 9. The raw materials and reaction conditions for other compounds remained unchanged, and the raw materials were all commercially available.

[0610] Compound 87:

[0611]

[0612] (E) and (Z)-9-((benzyloxy)imino)-2,3-dimethyl-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0613] 1H NMR (400MHz, DMSO-d6) δ8.99 (dd, J=8.0, 1.4Hz, 1H), 8.22-8.16 (m, 4H), 8.0 5(dd,J=7.8,1.6Hz,3H),7.73–7.68(m,1H),7.66–7.62(m,3H),7.58(td,J=7 .6,1.4Hz,3H),7.51–7.45(m,7H),7.39–7.31(m,8H),7.31–7.26(m,3H),5. 48(s,2H),5.46(s,5H),3.93(s,8H),3.87(s,3H),2.45(s,8H),2.40(s,3H).

[0614] HRMS(ESI): Theoretical value of m / z: C 17 H 19 N3O2[M+H] + 332.1394, measured value: 332.1398.

[0615] Compound 88:

[0616]

[0617] (E) and (Z)-11-((benzyloxy)imino)-2,3-dimethyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one

[0618] 1 H NMR (400MHz, DMSO-d6) δ8.69(d,J=10.2Hz,2H),8.13(d,J=8.2Hz,1H),8.05(d,J=8.0 Hz,1H),7.69–7.52(m,2H),7.39–7.31(m,3H),5.59(s,2H),4.03(s,3H),2.72(s,3H).

[0619] HRMS(ESI): Theoretical value of m / z: C 17 H 19 N3O2[M+H] + 382.1550, measured value: 382.1558.

[0620] Example 10

[0621] 4 g of 2,3,-diamino-1,4-benzoquinone was dissolved in 13 mL of dimethyl sulfoxide, and 2.5 mL of 3,4,5-trimethoxybenzaldehyde was added. The mixture was reacted in an open container at 80°C for 13 hours. After cooling to room temperature, water was slowly added, and the precipitated solid was filtered and dried under vacuum to obtain a yellow solid, 0.15 g of 2-(3,4,5-trimethoxyphenyl)-1,4-naphthoquinone imidazole. 0.4 g of naphthoquinone imidazole and 0.15 g of potassium hydroxide were added sequentially to a 3 mL solution of dimethyl sulfoxide. The mixture was stirred at 50°C for 30 minutes, and 0.17 mL of iodobutane was added. After reacting for 5 hours, water was added, and the precipitated solid was filtered, washed with water, and dried under vacuum to obtain a yellow solid, 0.35 g of 1-butyl-2-(3,4,5-trimethoxyphenyl)-1,4-naphthoquinone imidazole. Naphthoquinone imidazole (0.42 g), benzyloxyamine hydrochloride (0.64 g), and pyridine (0.7 mL) were dissolved in ethanol (70 mL) and reacted at 105 °C for 36 hours. After the reaction was completed, the mixture was concentrated and separated by silica gel column chromatography to obtain a pale yellow product (0.36 g).

[0622] 2,3,-Diamino-1,4-naphthoquinone (4 g) was dissolved in 13 mL of dimethyl sulfoxide and reacted with different aldehydes, or with different substituted aminooxyhydrochlorides, to prepare compounds 89-90 using the method of Example 10. The raw materials and reaction conditions for other compounds remained unchanged, and the raw materials were all commercially available.

[0623] Compound: 89:

[0624]

[0625] (E) and (Z)-9-((benzyloxy)imino)-3-butyl-2-(3,4,5-trimethoxyphenyl)-3,9-dihydro-4H-naphthol[2,3-d]imidazol-4-one

[0626] 1H NMR (400MHz, DMSO-d6) δ9.04(d,J=8.0Hz,1H),8.27(t,J=7.0Hz,2H),8.13(dd,J=7.8,1.6Hz,2H),7.72(dt, J=15.2,7.4Hz,3H),7.63(t,J=7.6Hz,2H),7.57–7.50(m,3H),7.47(d,J=7.4Hz,2H),7.40-7.18(m,14H),6. 98(s,3H),6.95(s,2H),5.52(s,2H),5.48(s,3H),4.53(s,3H),4.47(t,J=7.4Hz,3H),4.41(t,J=7.6Hz,2H) ,3.82(s,4H),3.80(s,7H),3.72(d,J=1.2Hz,5H),1.70-1.65(m,5H),1.21–1.15(m,5H),0.85-0.70(m,7H).

[0627] HRMS(ESI): Theoretical value of m / z: C 17 H 19 N3O2[M+H] + 526.2337, Measured value: 526.2337.

[0628] Compound 90:

[0629]

[0630] (E) and (Z)-2-cyclopropyl-11-(methoxyimino)-3-methyl-3,11-dihydro-4H-anthraquinone[2,3-d]imidazol-4-one

[0631] 1 H NMR (400MHz, DMSO-d6) δ8.55(s,2H),8.18-8.12(m,2H),7.73-7.60(m,2H),2.15-2.01(m,1H),1.12-0.97(m,4H),4.05(s,3H),3.84(s,3H).

[0632] HRMS(ESI): Theoretical value of m / z: C 17 H 19 N3O2[M+H] + 332.1394, measured value: 332.1395.

[0633] Example 11

[0634] Compound 1 (0.05 mmol) was reacted in 3 mL of acetonitrile with 31 μL of iodomethane at 120 °C for 24 h. After the reaction was complete, the solvent was removed to obtain a yellow solid, which was then slurried for half an hour and filtered to obtain the final product.

[0635] Using the different synthetic intermediates described above, compounds 91-118 can be prepared according to the method of Example 11. The raw materials and reaction conditions for the other compounds remain unchanged, and the raw materials are all commercially available.

[0636] Compound 91:

[0637]

[0638] (E)-1-Methyl-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0639] 1 H NMR (500MHz, DMSO-d6) δ14.50(s,1H),9.57(s,1H),9.25(dd,J=10.0,0.5Hz,1H),8.33(dd,J =10.0,1.0Hz,1H),8.01-7.93(m,1H),7.85(td,J=5.0,1.5Hz,1H),4.19(s,3H),4.10(s,3H).

[0640] 13 C NMR (126MHz, DMSO-d6) δ174.28,143.85,138.38,135.34,135.31,131.90,131.49,130.83,127.34,127.16,125.39,38.98,36.41.

[0641] HRMS (ESI-TOF) m / z theoretical value: C 13 H 12 N3O2[MI] + ,242.0924, Measured value: 242.0928.

[0642] Compound 92:

[0643]

[0644] (E)-1-Ethyl-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0645] 1H NMR (500MHz, DMSO-d6) δ14.49(s,1H),9.67(s,1H),9.26(dd,J=10.0,1.0Hz,1H),8.34(dd,J=10.0,1.0Hz,1H),7.9 6(td,J=10.0,1.5Hz,1H),7.85(td,J=10.0,1.0Hz,1H),4.63(q,J=7.5Hz,2H),4.11(s,3H),1.53(t,J=5.0Hz,3H).

[0646] 13 C NMR (126MHz, DMSO-d6) δ174.01,143.12,138.52,135.86,135.28,131.83,131.37,130.85,127.39,127.03,124.77,44.93,39.09,15.42.

[0647] HRMS (ESI-TOF) m / z theoretical value: C 14 H 14 N3O2[MI] + ,256.1081, Measured value: 256.1078.

[0648] Compound 93:

[0649]

[0650] (E)-4-(hydroxyimino)-3-methyl-9-oxo-1-propyl-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0651] 1 H NMR(500MHz,DMSO-d6)δ14.51(s,1H),9.67(s,1H),9.25(dd,J=10.0,1.0Hz,1H),8.34(dd,J=10.0,1.5Hz,1H),8.00-7 .93(m,1H),7.85(td,J=10.0,1.0Hz,1H),4.57(t,J=7.0Hz,2H),4.11(s,3H),1.96-1.85(m,2H),0.96(t,J=7.5Hz,3H).

[0652] 13C NMR (126MHz, DMSO-d6) δ174.09,143.40,138.51,135.95,135.29,131.88,131.43,130.91,127.42,127.08,124.84,50.68,39.17,23.13,10.92.

[0653] HRMS (ESI-TOF) m / z theoretical value: C 15 H 16 N3O2[MI] + ,270.1237, Measured value: 270.1244.

[0654] Compound 94:

[0655]

[0656] (E)-1-Butyl-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0657] 1 H NMR (500MHz, DMSO-d6) δ14.50(s,1H),9.67(s,1H),9.25(dd,J=10.0,0.5Hz,1H),8.34(dd,J=10.0,1.5Hz,1H),7.96(td,J=10.0,1.5H z,1H),7.85(td,J=10.0,1.5Hz,1H),4.60(t,J=7.0Hz,2H),4.10(s,3H),1.91-1.85(m,2H),1.44-1.33(m,2H),0.95(t,J=7.5Hz,3H).

[0658] 13 C NMR(126MHz,DMSO-d6)δ174.06,143.37,138.52,135.93,135.28,131.85,1 31.40,130.89,127.42,127.06,124.80,49.00,39.16,31.69,19.28,13.86.

[0659] HRMS (ESI-TOF) m / z theoretical value: C 16 H 18 N3O2[MI] + ,284.1394, Measured value: 284.1393.

[0660] Compound 95:

[0661]

[0662] (E)-4-(hydroxyimino)-1-isopropyl-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0663] 1 H NMR (400MHz, DMSO-d6) δ14.50(s,1H),9.81(s,1H),9.24(dd,J=8.0,1.2Hz,1H),8.35(dd,J=8.0,1.6Hz,1 H),8.04-7.90(m,1H),7.85(td,J=8.0,1.2Hz,1H),5.49-5.40(m,1H),4.11(s,3H),1.61(d,J=8.0Hz,6H).

[0664] 13 C NMR (101MHz, DMSO-d6) δ174.04,141.76,138.52,135.96,135.23,131.88,131.36,131.04,127.51,126.85,124.69,52.90,39.23,22.54.

[0665] HRMS (ESI-TOF) m / z theoretical value: C 15 H 16 N3O2[MI] + ,270.12374, Measured value: 270.1237.:

[0666] Compound 96:

[0667]

[0668] (E)-4-(hydroxyimino)-1-isobutyl-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0669] 1 H NMR (500MHz, DMSO-d6) δ14.51(s,1H),9.68(s,1H),9.25(dd,J=10.0,0.5Hz,1H),8.33(dd,J=10.0,1.0Hz,1H),7.99-7. 93(m,1H),7.85(td,J=10.0,1.0Hz,1H),4.44(d,J=10.0Hz,2H),4.12(s,3H),2.27-2.10(m,1H),0.98(d,J=5.0Hz,6H).

[0670] 13 C NMR (126MHz, DMSO-d6) δ174.14,143.52,138.52,136.06,135.31,131.87,131.41,130.92,127.42,127.08,124.84,55.59,39.26,29.14,19.66.

[0671] HRMS (ESI-TOF) m / z theoretical value: C 16 H 18 N3O2[MI] + ,284.1394, Measured value: 284.1387.

[0672] Compound 97:

[0673]

[0674] (E)-4-(hydroxyimino)-3-methyl-1-(2-methylbutyl)-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0675] 1 H NMR (400MHz, DMSO-d6) δ14.50(s,1H),9.69(s,1H),9.25(dd,J=8.0,0.8Hz,1H),8.33(dd,J=8.0,1.4Hz,1H),8.01-7.91(m,1H),7.84(td,J=8.0,1. 2Hz,1H),4.56(dd,J=12.0,4.0Hz,1H),4.42-4.35(m,1H),4.12(s,3H),2. 07-1.90(m,1H),1.53-1.40(m,1H),1.33-1.19(m,1H),1.00-0.87(m,6H).

[0676] 13 C NMR(101MHz,DMSO-d6)δ174.12,143.58,138.52,136.06,135.29,131.86,131. 40,130.91,127.43,127.07,124.87,54.38,39.27,35.19,26.25,16.46,11.30.

[0677] HRMS (ESI-TOF) m / z theoretical value: C 17 H 20 N3O2[MI] +,298.1550, Measured value: 298.1551.

[0678] Compound 98:

[0679]

[0680] (E)-1-(tert-butyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0681] 1 H NMR (400MHz, DMSO-d6) δ14.50 (s, 1H), 9.67 (s, 1H), 9.19 (dd, J = 8.0, 1.2Hz, 1H), 8.38 ( dd,J=8.0,1.4Hz,1H),7.98-7.91(m,1H),7.89-7.79(m,1H),4.11(s,3H),1.81(s,9H).

[0682] 13 C NMR (101MHz, DMSO-d6) δ173.08,142.92,138.84,138.42,134.98,131.90,131.45,130.93,1210.06,126.24,126.02,63.89,36.40,28.72.

[0683] HRMS (ESI-TOF) m / z theoretical value: C 16 H 18 N3O2[MI] + ,284.1394, Measured value: 284.1395.

[0684] Compound 99:

[0685]

[0686] (E)-1-Cyclopropyl-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0687] 1H NMR(500MHz,DMSO-d6)δ14.48(s,1H),9.73(s,1H),9.31-9.16(m,1H),8.35(dd,J=10.0,1.5Hz,1H),7.96 (td,J=10.0,1.0Hz,1H),7.86(td,J=10.0,1.0Hz,1H),4.16-4.05(m,1H),4.06(s,3H),1.31-1.18(m,4H).

[0688] 13 C NMR (126MHz, DMSO-d6) δ173.42,143.46,138.43,135.56,135.19,131.93,131.43,131.00,127.40,126.93,126.42,39.02,31.83,7.48.

[0689] HRMS (ESI-TOF) m / z theoretical value: C 15 H 14 N3O2[MI] + ,268.1081, Measured value: 268.1081.

[0690] Compound 100:

[0691]

[0692] (E)-4-(hydroxyimino)-1-(2-methoxyethyl)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0693] 1 H NMR (500MHz, DMSO-d6) δ14.51(s,1H),9.65(s,1H),9.25(d,J=10.0,1H),8.33(dd,J=10.0,1.5Hz,1H),7.97(td,J=10 .0,1.5Hz,1H),7.85(td,J=10.0,1.0Hz,1H),4.81(t,J=5.0Hz,2H),4.14(s,3H),3.81(t,J=5.0Hz,2H),3.30(s,3H).

[0694] 13C NMR (126MHz, DMSO-d6) δ174.24,143.67,138.44,135.78,135.33,131.86,131.44,130.88,127.41,127.09,124.77,69.37,58.66,48.91,39.15.

[0695] HRMS (ESI-TOF) m / z theoretical value: C 15 H 16 N3O3[MI] + ,286.1186, Measured value: 286.1187.:

[0696] Compound 101:

[0697]

[0698] (E)-4-(hydroxyimino)-3-methyl-1-(3-methyl-2-en-1-yl)-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0699] 1 H NMR (500MHz, DMSO-d6) δ14.50(s,1H),9.62(s,1H),9.25(dd,J=10.0,1.0Hz,1H),8.34(dd,J=10.0,1.5Hz,1H),7.96(td,J=10 .0,1.5Hz,1H),7.85(td,J=10.0,1.0Hz,1H),5.55-5.45(m,1H),5.22(d,J=5.0Hz,2H),4.11(s,3H),1.84(s,3H),1.80(s,3H).

[0700] 13 C NMR(126MHz,DMSO-d6)δ174.14,142.89,141.39,138.44,135.86,135.31,131.8 9,131.45,130.86,127.42,127.07,124.81,116.94,47.08,39.11,26.02,18.66.

[0701] HRMS (ESI-TOF) m / z theoretical value: C 17 H 18 N3O2[MI] + ,296.1394, Measured value: 296.1390.

[0702] Compound 102:

[0703]

[0704] (E)-1-Benzyl-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0705] 1 H NMR (500MHz, DMSO-d6) δ14.53(s,1H),9.76(s,1H),9.24(d,J=10.0Hz,1H),8.30(dd,J=10.0,1.5Hz,1H),7.95(td, J=10.0,1.5Hz,1H),7.83(td,J=10.0,1.0Hz,1H),7.51-7.45(m,2H),7.45-7.36(m,3H),5.88(s,2H),4.13(s,3H).

[0706] 13 C NMR(126MHz,DMSO-d6)δ174.00,143.75,138.46,136.14,135.37,134.74,131.87 ,131.44,130.76,129.34,129.11,128.56,127.39,127.12,124.57,51.80,39.35.

[0707] HRMS (ESI-TOF) m / z theoretical value: C 19 H 16 N3O2[MI] + ,318.1237, Measured value: 318.1233.

[0708] Compound 103:

[0709]

[0710] (E)-1-(2-ethoxy-2-oxoethyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0711] 1H NMR (500MHz, DMSO-d6) δ14.62(s,1H),9.61(s,1H),9.27(d,J=10.0Hz,1H),8.30(dd,J=10.0,1.5Hz,1H),7.99(t d,J=10.0,1.5Hz,1H),7.88-7.82(m,1H),5.58(s,2H),4.26(q,J=7.0Hz,2H),4.19(s,3H),1.27(t,J=7.0Hz,3H).

[0712] 13 C NMR(126MHz,DMSO-d6)δ174.04,166.57,144.24,138.22,135.63,135.54,13 1.97,131.59,130.42,127.36,127.23,124.83,62.54,49.97,39.38,14.51.

[0713] HRMS (ESI-TOF) m / z theoretical value: C 16 H 16 N3O4[MI] + ,314.1135, Measured value: 314.1138.:

[0714] Compound 104:

[0715]

[0716] (E)-4-(hydroxyimino)-3-methyl-9-oxo-1-phenyl-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0717] 1 H NMR(500MHz,DMSO-d6)δ14.60(s,1H),10.00(s,1H),9.28(d,J=5.0,Hz,1H),8.23(dd,J=10.0,1.5Hz,1 H),8.01-7.95(m,1H),7.84(td,J=10.0,1.0Hz,1H),7.77-7.74(m,2H),7.71-7.67(m,3H),4.19(s,3H).

[0718] 13C NMR(126MHz,DMSO-d6)δ172.91,144.41,138.47,135.61,135.26,133.99,131 .95,131.41,131.18,131.04,129.83,127.44,126.91,126.62,125.20,39.40.

[0719] HRMS (ESI-TOF) m / z theoretical value: C 18 H 14 N3O2[MI] + ,304.1081, Measured value: 304.1085.

[0720] Compound 105:

[0721]

[0722] (E)-4-(hydroxyimino)-1-trimethyl-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0723] 1 H NMR (500MHz, DMSO-d6) δ14.58(s,1H),9.81(s,1H),9.29(dd,J=10.0,0.5Hz,1H),8.18(dd,J=10.0,1.0Hz, 1H),8.03-7.93(m,1H),7.82(td,J=10.0,1.0Hz,1H),7.16(s,2H),4.20(s,3H),2.38(s,3H),2.04(s,6H).

[0724] 13 C NMR(126MHz,DMSO-d6)δ173.08,144.26,140.75,138.74,136.36,135.27,135.12,13 1.82,131.44,130.87,130.41,129.56,127.35,127.27,124.97,39.78,21.15,17.54.

[0725] HRMS (ESI-TOF) m / z theoretical value: C 21 H 20 N3O2[MI] + ,346.1550, Measured value: 346.1555.

[0726] Compound 106:

[0727]

[0728] (E)-4-(hydroxyimino)-3-methyl-9-oxo-1-(thiophen-2-ylmethyl)-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0729] 1 H NMR (400MHz, DMSO-d6) δ13.01(s,1H),8.49(s,1H),8.27(d,J=7.8Hz,1H),8.12(dd,J=8.0,1.6Hz,1H),7.69(t,J=7.6Hz,1H) ,7.60(t,J=7.1Hz,1H),7.43(d,J=5.9Hz,1H),7.19(d,J=3.0Hz,1H),6.95(dd,J=5.1,3.5Hz,1H),5.88(s,2H),4.28(s,3H).

[0730] Theoretical value of HRMS (ESI-TOF) m / z: C17H14N3O2S[MI]+, 324.0801, measured value: 324.0802.

[0731] Compound 107:

[0732]

[0733] (E)-1-((1,3-dioxane-2-yl)methyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0734] 1 H NMR (500MHz, DMSO-d6) δ14.53(s,1H),9.64(s,1H),9.25(dd,J=10.0,0.5Hz,1H),8.33(dd,J=10.0,1.5Hz,1H),8.01 -7.93(m,1H),7.85(td,J=10.0,1.0Hz,1H),5.34(t,J=3.5Hz,1H),4.91(d,J=5.0Hz,2H),4.16(s,3H),3.86(s,4H).

[0735] 13 C NMR (126MHz, DMSO-d6) δ174.18,144.11,138.36,135.52,135.39,131.89,131.45,130.83,127.43,127.06,125.01,99.99,65.37,49.50,39.28.

[0736] HRMS (ESI-TOF) m / z theoretical value: C 16 H 15 N3O4[MI] + ,314.1135, Measured value: 314.1136.

[0737] Compound 108:

[0738]

[0739] (E)-1-(4-fluorobenzyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0740] 1 H NMR (500MHz, DMSO-d6) δ14.54(s,1H),9.71(s,1H),9.24(dd,J=10.0,0.5Hz,1H),8.31(dd,J=10.0,1.5Hz,1H),7.96(td,J=10 .0,1.5Hz,1H),7.83(td,J=10.0,1.0Hz,1H),7.57(dd,J=10.0,5.0Hz,2H),7.28(t,J=10.0Hz,2H),5.85(s,2H),4.12(s,3H).

[0741] 13 C NMR(126MHz,DMSO-d6)δ174.02,163.66(161.71,J=243.8Hz),143.70,138.45,136.13,135.39,131.89,131.45,131.20(1 31.14, J=7.5Hz), 130.89 (130.87, J=2.5Hz), 130.76, 127.40, 127.12, 124.57, 116.29 (116.12, J=21.3Hz), 51.15, 39.33.

[0742] HRMS (ESI-TOF) m / z theoretical value: C 19 H 15 FN3O2[MI] + ,336.1143, Measured value: 336.1138.

[0743] Compound 109:

[0744]

[0745] (E)-1-(2-fluorophenyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0746] 1 H NMR (500MHz, DMSO-d6) δ14.68(s,1H),10.08(s,1H),9.29(dd,J=10.0,1.0Hz,1H),8.24(dd,J=10.0,1.5Hz ,1H),8.03-7.95(m,1H),7.89-7.77(m,3H),7.68-7.61(m,1H),7.54(td,J=10.0,1.0Hz,1H),4.21(s,3H).

[0747] 13 C NMR (126MHz, DMSO) δ172.95, 157.58 (155.57, J = 251.3Hz), 145.03, 138.34, 135.74, 135.52, 133.83 (133.77, J = 7.5Hz), 132.01, 131.52 ,130.65,128.91,127.34,127.06,125.88(125.85,J=3.8Hz),125.17,121.97(121.87,J=12.5Hz),117.28(117.13,J=18.8Hz),39.62.

[0748] HRMS (ESI-TOF) m / z theoretical value: C 18 H 13 FN3O2[MI] + ,322.0986, Measured value: 322.0986.

[0749] Compound 110:

[0750]

[0751] (E)-1-(3-fluorophenyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0752] 1H NMR (400MHz, DMSO-d6) δ14.64(s,1H),10.04(d,J=0.4Hz,1H),9.28(dd,J=8.0,0.8Hz,1H),8.25(dd,J=8.0,1 .2Hz,1H),8.03-7.95(m,1H),7.85(td,J=8.0,1.2Hz,1H),7.80-7.71(m,2H),7.66-7.54(m,2H),4.20(s,3H).

[0753] 13 C NMR (101MHz, DMSO) δ172.90, 163.16 (160.72, J = 244.0Hz), 144.62, 138.38, 135.43, 135.33, 135.07 (134.96, J = 11.0Hz), 131.98, 131.76 (131.67 ,J=9.0Hz),131.41,130.99,127.49,126.87,125.21,123.05(123.02,J= 3.0Hz), 118.47 (118.26, J=21.0Hz), 114.78 (114.53, J=25.0Hz), 39.45.

[0754] HRMS (ESI-TOF) m / z theoretical value: C 18 H 13 FN3O2[MI] + ,322.0986, Measured value: 322.0982.

[0755] Compound 111:

[0756]

[0757] (E)-1-(4-fluorophenyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0758] 1 H NMR (400MHz, DMSO-d6) δ14.60(s,1H),9.96(s,1H),9.26(d,J=8.0Hz,1H),8.22(d,J=8. 0Hz,1H),7.95(t,J=8.0Hz,1H),7.86-7.72(m,3H),7.54(t,J=8.0Hz,2H),4.17(s,3H).

[0759] 13C NMR (126MHz, DMSO) δ172.97, 164.38 (162.40, J = 1910.0Hz), 144.56, 138.40, 135.41 (135.31, J = 10.0Hz), 131.97, 131. 44,130.99,130.26,130.24,129.22(129.14,J=10.0Hz),127.44,126.91,125.32,116.93(116.74,J=19.0Hz),39.39.

[0760] HRMS (ESI-TOF) m / z theoretical value: C 18 H 13 FN3O2[MI] + ,322.0986, Measured value: 322.0991.

[0761] Compound 112:

[0762]

[0763] (E)-1-(2-fluorobenzyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0764] 1 H NMR (500MHz, DMSO-d6) δ14.55(s,1H),9.71(s,1H),9.25(dd,J=10.0,1.0Hz,1H),8.29(dd,J=10.0,1.5Hz,1H),7.96(td,J=10.0,1.5 Hz,1H),7.83(td,J=10.0,1.0Hz,1H),7.52-7.43(m,2H),7.37-7.30(m,1H),7.24(td,J=10.0,1.0Hz,1H),5.94(s,2H),4.14(s,3H).

[0765] 13C NMR(126MHz,DMSO-d6)δ173.93,161.62(159.66,J=245.0Hz),144.04,138 .44,136.14,135.42,131.90,131.61(131.55,J=7.5Hz),131.46,130.70,1 30.67,127.40,127.13,125.35(125.32,J=3.8Hz),124.67,121.80(121.6 9, J=13.8Hz), 116.23 (116.07, J=20.0Hz), 46.44 (46.41, J=3.8Hz), 39.32.

[0766] HRMS (ESI-TOF) m / z theoretical value: C 19 H 15 FN3O2[MI] + ,336.1143, Measured value: 336.1145.

[0767] Compound 113:

[0768]

[0769] (E)-1-(3-fluorobenzyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0770] 1 H NMR (500MHz, DMSO-d6) δ14.55(s,1H),9.74(s,1H),9.25(dd,J=10.0,1.0Hz,1H),8.30(dd,J=10.0,2.0Hz,1H),7.96(td,J=10. 0,1.5Hz,1H),7.83(td,J=10.0,1.0Hz,1H),7.50-7.45(m,1H),7.36-7.29(m,2H),7.26-7.18(m,1H),5.89(s,2H),4.13(s,3H).

[0771] 13C NMR (126MHz, DMSO-d6) δ173.96, 163.70 (161.76, J = 242.5Hz), 143.95, 138.48, 137.47 (137.41, J = 7.5Hz), 136.15, 135.39, 131.88, 131.45, 131.39 (131.32, J = 8.8Hz), 130.75, 127.40, 127.15, 124.61, 124.59, 115.98 (115.82, J = 20.0Hz), 115.41 (115.23, J = 22.5Hz), 51.21, 39.38.

[0772] HRMS (ESI-TOF) m / z theoretical value: C 19 H 15 FN3O2[MI] + ,336.1143, Measured value: 336.1146.

[0773] Compound 114:

[0774]

[0775] (E)-4-(hydroxyimino)-1-(4-methoxyphenyl)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0776] 1 H NMR (500MHz, DMSO-d6) δ14.58(s,1H),9.92(s,1H),9.27(dd,J=10.0,1.0Hz,1H),8.24(dd,J=10.0,1.5Hz,1H),8.01- 7.93(m,1H),7.84(td,J=10.0,1.5Hz,1H),7.66(d,J=10.0Hz,2H),7.21(d,J=10.0Hz,2H),4.17(s,3H),3.89(s,3H).

[0777] 13 C NMR (126MHz, DMSO-d6) δ172.93,161.12,144.32,138.47,135.44,135.22,131.94 ,131.40,131.08,127.96,127.42,126.91,126.64,125.31,114.85,56.23,39.30.

[0778] HRMS (ESI-TOF) m / z theoretical value: C 19 H16 N3O3[MI] + ,334.1186, Measured value: 334.1184.

[0779] Compound 115:

[0780]

[0781] (E)-4-(hydroxyimino)-1-(4-methoxybenzyl)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0782] 1 H NMR (500MHz, DMSO-d6) δ14.51(s,1H),9.68(s,1H),9.23(dd,J=10.0,1.0Hz,1H),8.32(dd,J=10.0,1.0Hz,1H),7.99-7 .91(m,1H),7.83(td,J=10.0,1.0Hz,1H),7.52-7.45(m,2H),7.04-6.96(m,2H),5.79(s,2H),4.10(s,3H),3.76(s,3H).

[0783] 13 C NMR(126MHz,DMSO-d6)δ174.06,160.08,143.40,138.44,136.09,135.36,131.88,13 1.43,130.78,130.66,127.41,127.09,126.36,124.56,114.74,55.72,51.49,39.29.

[0784] HRMS (ESI-TOF) m / z theoretical value: C 20 H 18 N3O3[MI] + ,348.1343, Measured value: 348.1347.

[0785] Compound 116:

[0786]

[0787] (E)-1-(3-chloro-4-fluorophenyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0788] 1H NMR (500MHz, DMSO-d6) δ14.66(s,1H),10.02(s,1H),9.28(dd,J=10.0,1.0Hz,1H),8.26(dd,J=10.0,1 .5Hz,1H),8.17(dd,J=10.0,2.5Hz,1H),7.99(td,J=5.0,1.5Hz,1H),7.88-7.77(m,3H),4.20(s,3H).

[0789] 13 C NMR(126MHz,DMSO-d6)δ173.01,159.77(157.78,J=250.0Hz),144.77,138.33,135.39,135.23,132.01,131.44,130.92,130.75(130.72, J=3.8Hz), 129.46, 128.10 (1210.03, J=8.8Hz), 127.49, 126.88, 125.30, 120.56 (120.40, J=20.0Hz), 118.20 (118.02, J=22.5Hz), 39.46.

[0790] HRMS (ESI-TOF) m / z theoretical value: C 18 H 12 ClFN3O2[MI] + ,356.0597, Measured value: 356.0593.

[0791] Compound 117:

[0792]

[0793] (E)-1-(3-bromo-4-fluorophenyl)-4-(hydroxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0794] 1 H NMR (400MHz, DMSO-d6) δ14.65 (s, 1H), 10.02 (s, 1H), 9.28 (dd, J = 8.0, 1.2Hz, 1H), 8.33- 8.20(m,2H),8.02-7.95(m,1H),7.90-7.80(m,2H),7.75(t,J=8.0Hz,1H),4.19(s,3H).

[0795] 13C NMR (101MHz, DMSO) δ173.01, 161.09 (158.62, J = 247.0Hz), 144.79, 138.33, 135.38, 135.20, 132.12 (131.99, J = 13.0Hz), 131.44, 130.9 7,130.93,130.92,128.70(128.61,J=9.0Hz),127.48,126.88,125.32,117.93(117.69,J=24.0Hz),108.84(108.62,J=22.0Hz),39.44.

[0796] HRMS (ESI-TOF) m / z theoretical value: C 18 H 12 BrFN3O2[MI] + ,400.0091, Measured value: 400.0088.

[0797] Compound 118:

[0798]

[0799] (E)-4-(hydroxyimino)-1,3-dimethyl-5-nitro-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0800] 1H NMR (400MHz, DMSO-d6) δ14.67(s,1H),9.67(s,1H),8.41(d,J=7.8Hz,1H),8.30(d,J=7.9Hz,1H),8.19(t,J=7.8Hz,1H),4.14(d,J=21.7Hz,6H).

[0801] HRMS (ESI-TOF) m / z theoretical value: C 18 H 12 BrFN3O2[MI] + ,287.0775, Measured value: 287.0778.

[0802] Example 12

[0803] Compound 1 (0.05 mmol) was reacted in 3 mL of acetonitrile with 310 μL of iodomethane at 70 °C for 48 hours. After the reaction was complete, the solvent was removed to obtain a yellow solid, which was then slurried for half an hour and filtered to obtain the final product.

[0804] Using the different synthetic intermediates described above, compounds 119-126 can be prepared according to the method of Example 12. The raw materials and reaction conditions for the other compounds remain unchanged, and the raw materials are all commercially available.

[0805] Compound 119:

[0806]

[0807] (E) and (Z)-1-Butyl-4-(methoxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0808] 1 H NMR(500MHz, DMSO-d6)δ9.65(s,1H),9.02(dd,J=5.0,0.5Hz,1H),8.35(dd,J=10.0,1.0Hz,1H),7.99-7.92(m,1H),7.88(td,J= 5.0,1.0Hz,1H),4.60(t,J=7.0Hz,2H),4.41(s,3H),4.13(s,3H),1.93-1.81(m,2H),1.43-1.35(m,2H),0.95(t,J=5.0Hz,3H).

[0809] 13 C NMR (126MHz, DMSO-d6) δ173.98,143.58,138.41,135.35,134.86,132.54,131. 66,131.22,127.73,126.70,125.33,66.37,49.06,39.25,31.67,19.28,13.86.

[0810] HRMS (ESI-TOF) m / z theoretical value: C 17 H 20 N3O2[MI] + ,298.1550, Measured value: 298.1555.

[0811] Compound 120:

[0812]

[0813] (E) and (Z)-1-Butyl-4-(ethoxyimino)-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0814] Yellow solid, melting point: 134-136℃.

[0815] 1 H NMR (500MHz, DMSO-d6) δ9.67 (s, 1H), 9.05 (d, J = 10.0Hz, 1H), 8.34 (dd, J = 10.0, 1.5Hz, 1H), 7.98 (td, J = 10.0 1.5Hz,1H),7.88(td,J=10.0,1.0Hz,1H),4.67(q,J=7.0Hz,2H),4.60(t,J=7.0Hz,2H),4.13 (s,3H),1.94-1.82(m,2H),1.50(t,J=7.0Hz,3H),1.42-1.33(m,2H),0.95(t,J=7.5Hz,3H).

[0816] 13 C NMR(126MHz,DMSO-d6)δ173.97,143.54,138.27,135.36,135.06,132.45,131.55, 131.19,127.70,126.73,125.24,74.48,49.06,39.33,31.67,19.28,15.04,13.87.

[0817] HRMS (ESI-TOF) m / z theoretical value: C 18 H 22 N3O2[MI] + ,312.1707, Measured value: 312.1707.

[0818] Compound 121:

[0819]

[0820] (E) and (Z)-4-((benzyloxy)imino)-1-butyl-3-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0821] Yellow solid, melting point: 122-124℃.

[0822] 1H NMR(500MHz,DMSO-d6)δ9.62(s,1H),9.09(d,J=10.0Hz,1H),8.34(dd,J=10.0,1.0Hz,1H),8.01-7.94(m,1H),7.88(td,J=10.0,1.0Hz,1H),7. 61-7.54(m,2H),7.48-7.37(m,3H),5.68(s,2H),4.57(t,J=7.0Hz,2H) ,4.03(s,3H),1.90-1.77(m,2H),1.41-1.32(m,2H),0.97-0.90(m,3H).

[0823] 13 C NMR (126MHz, DMSO) δ173.94,143.58,138.73,136.71,135.39,134.89,132.57,131.60,131.25 ,129.47,129.21,129.18,127.76,126.70,125.35,80.08,49.03,39.33,31.66,19.24,13.85.

[0824] HRMS (ESI-TOF) m / z theoretical value: C 23 H 23 N3O2[MI] + ,374.1863, Measured value: 374.1863.

[0825] Compound 122:

[0826]

[0827] (E) and (Z)-1-Butyl-3-ethyl-4-(methoxyimino)-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0828] Yellow solid, melting point: 135-137℃.

[0829] 1H NMR (500MHz, DMSO-d6) δ9.71(s,1H),9.02(d,J=10.0Hz,1H),8.34(d,J=10.0,1H),7.97(td,J=10.0,1.5Hz,1H),7.88(t,J=1 0.0,1H),4.65-4.55(m,5H),4.41(s,3H),1.92-1.83(m,3H),1.54(t,J=7.0Hz,3H),1.47-1.35(m,3H),0.95(t,J=7.0Hz,4H).

[0830] 13 C NMR(126MHz,DMSO-d6)δ174.09,142.86,138.14,135.34,134.19,132.51,131.70, 131.11,127.70,126.81,125.71,66.27,49.20,47.07,31.65,19.35,14.86,13.89.

[0831] HRMS (ESI-TOF) m / z theoretical value: C 18 H 22 N3O2[MI] + ,312.1707, Measured value: 312.1708.

[0832] Compound 123:

[0833]

[0834] (E) and (Z)-4-(methoxyimino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0835] Yellow solid, melting point: 167-169℃.

[0836] 1 H NMR (400MHz, DMSO-d6) δ9.58 (s, 1H), 9.01 (d, J = 8.0, 1H), 8.33 (dd, J = 4.0, 1.2Hz, 1H), 7.97 (td,J=8.0,1.6Hz,1H),7.88(td,J=8.0,1.2Hz,1H),4.41(s,3H),4.18(s,3H),4.13(s,3H).

[0837] 13C NMR (101MHz, DMSO) δ174.16,144.05,138.25,135.38,134.26,132.56,131.72,131.10,127.63,126.76,125.85,66.37,39.08,36.44.

[0838] HRMS (ESI-TOF) m / z theoretical value: C 14 H 14 N3O2[MI] + ,256.1081, Measured value: 256.1085.

[0839] Compound 124:

[0840]

[0841] (E) and (Z)-4-(ethoxyimino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0842] Yellow solid, melting point: 165-167℃.

[0843] 1 H NMR (500MHz, DMSO-d6) δ9.57(s,1H),9.06(dd,J=10.0,1.0Hz,1H),8.34(dd,J=10.0,1.0Hz,1H),7.98(td,J=10.0 ,1.5Hz,1H),7.88(td,J=5.0,1.0Hz,1H),4.67(q,J=7.0Hz,2H),4.18(s,3H),4.13(s,3H),1.50(t,J=7.0Hz,3H).

[0844] 13 C NMR (126MHz, DMSO-d6) δ174.18,144.02,138.15,135.39,134.49,132.49,131.62,131.11,127.63,126.81,125.80,74.48,39.12,36.43,15.02.

[0845] HRMS (ESI-TOF) m / z theoretical value: C 15 H 15 N3O2[MI] + ,270.1243, Measured value: 270.1244.

[0846] Compound 125:

[0847]

[0848] (E)-4-((benzyloxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0849] Yellow solid, melting point: 177-179℃.

[0850] 1 H NMR(500MHz,DMSO-d6)δ9.53(s,1H),9.08(dd,J=10.0,1.0Hz,1H),8.33(dd,J=10.0,1.0Hz,1H),8.01-7.93(m, 1H),7.88(td,J=10.0,1.0Hz,1H),7.60-7.55(m,2H),7.49-7.38(m,3H),5.68(s,2H),4.16(s,3H),4.03(s,3H).

[0851] 13 C NMR(126MHz,DMSO-d6)δ174.15,144.04,138.61,136.66,135.42,134.32,132.61,13 1.66,131.16,129.49,129.23,129.19,127.67,126.77,125.90,80.09,39.13,36.39.

[0852] (Z)-4-((benzyloxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0853] 1 H NMR (400MHz, DMSO-d6) δ9.57(s,1H),8.22(d,J=8.1Hz,1H),8.15(d,J=7.8Hz,1H),7.86(t,J=7.7Hz,1H),7 .75(t,J=7.6Hz,1H),7.54(d,J=7.1Hz,2H),7.41(d,J=8.2Hz,3H),5.57(s,2H),4.13(s,3H),4.00(s,3H).

[0854] (E) and (Z)-4-((benzyloxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0855] 1H NMR (400MHz, DMSO-d6) δ9.55(s,3H),9.50(s,1H),9.04(d,J=8.0Hz,1H),8.29(dd,J=8.0 ,1.6Hz,1H),8.20(dd,J=8.0,1.2Hz,3H),8.13(dd,J=7.8,1.4Hz,3H),7.97–7.90(m,1H) ,7.84(td,J=7.6,1.6Hz,4H),7.73(td,J=7.6,1.2Hz,3H),7.59–7.48(m,8H),7.47–7.33 (m,12H),5.64(s,2H),5.55(s,6H),4.11(s,3H),4.11(s,6H),3.99(s,3H),3.98(s,6H).

[0856] HRMS (ESI-TOF) m / z theoretical value: C 20 H 18 N3O2[MI] + ,332.1394, Measured value: 332.1402.

[0857] Compound 126:

[0858]

[0859] (E) and (Z)-3-ethyl-4-(methoxyimino)-1-methyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0860] Yellow solid, melting point: 162-164℃.

[0861] 1 H NMR (500MHz, DMSO-d6) δ9.57(s,1H),9.06(d,J=10.0Hz,1H),8.34(dd,J=10.0,2.0Hz,1H),7.98(td,J=10.0,2. 0Hz,1H),7.88(td,J=10.0,1.5Hz,1H),4.67(q,J=7.0Hz,2H),4.18(s,3H),4.13(s,3H),1.50(t,J=7.0Hz,3H).

[0862] 13C NMR (126MHz, DMSO-d6) δ174.18,144.02,138.15,135.39,134.49,132.49,131.62,131.11,127.63,126.81,125.80,74.48,39.12,36.43,15.02.

[0863] HRMS (ESI-TOF) m / z theoretical value: C 15 H 16 N3O2[MI] + ,270.1237, Measured value: 270.1241.

[0864] Example 13

[0865] Compound 1 (0.05 mmol) was added to 3 mL of acetonitrile with 150 μL of iodomethane and reacted at 100 °C for 8 hours. After the reaction was complete, the solvent was removed to obtain a yellow solid, which was then slurried for half an hour and filtered to obtain the final product.

[0866] Using the different synthetic intermediates described above, compounds 127-151 can be prepared according to the method of Example 13. The raw materials and reaction conditions for the other compounds remain unchanged, and the raw materials are all commercially available.

[0867] Compound 127:

[0868]

[0869] (E) and (Z)-4-(isopropoxyimino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0870] Yellow solid, melting point: 187-189℃.

[0871] 1 H NMR(400MHz, DMSO-d6)δ9.58(s,1H),9.07(dd,J=8.0,0.4Hz,1H),8.34(dd,J=8.0,1.2Hz,1H),8.03-7.95 (m,1H),7.88(td,J=8.0,1.2Hz,1H),4.92-4.82(m,1H),4.18(s,3H),4.14(s,3H),1.51(d,J=8.0Hz,6H).

[0872] 13C NMR (101MHz, DMSO-d6) δ174.16,143.98,137.79,135.40,134.67,132.39,131.52,131.09,127.60,126.84,125.73,81.42,39.23,36.45,21.77.

[0873] HRMS (ESI-TOF) m / z theoretical value: C 16 H 18 N3O2[MI] + ,284.1394, Measured value: 284.1399.

[0874] Compound 128:

[0875]

[0876] (E) and (Z)-4-(butoxyimino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0877] Yellow solid, melting point: 201-203℃.

[0878] 1 H NMR(500MHz,DMSO-d6)δ9.59(s,1H),9.03(dd,J=8.0,1.0Hz,1H),8.34(dd,J=8.0,1.5Hz,1H),8.02–7.93(m,1H),7.90–7 .85(m,1H),4.64(t,J=6.5Hz,2H),4.18(s,3H),4.12(s,3H),1.95–1.77(m,2H),1.53–1.42(m,2H),0.98(t,J=7.5Hz,3H).

[0879] 13 C NMR (126MHz, DMSO-d6) δ174.16,144.02,138.15,135.43,134.46,132.49,131. 48,131.10,127.64,126.80,125.78,78.53,39.11,36.43,31.07,19.09,14.20.

[0880] HRMS (ESI-TOF) m / z theoretical value: C 17 H 20 N3O2[MI] + ,298.1550, Measured value: 298.1551.

[0881] Compound 129:

[0882]

[0883] (E) and (Z)-4-(isobutoxyimino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0884] Yellow solid, melting point: 139-141℃.

[0885] 1 H NMR (500MHz, DMSO-d6) δ9.57 (s, 1H), 9.03 (J = 10.0Hz, 1H), 8.35 (dd, J = 10.0, 1.5Hz, 1H), 8.05-7.98 (m, 1H), 7. 89(t,J=7.5Hz,1H),4.44(d,J=6.5Hz,2H),4.18(s,3H),4.12(s,3H),2.30-2.15(m,1H),1.05(d,J=5.0Hz,6H).

[0886] 13 C NMR(126MHz,DMSO-d6)δ174.16,144.03,138.16,135.45,134.47,132.51,1 31.41,131.13,127.69,126.82,125.81,84.91,39.11,36.43,28.32,19.37.

[0887] HRMS (ESI-TOF) m / z theoretical value: C 17 H 20 N3O2[MI] + ,298.1550, Measured value: 298.1551.

[0888] Compound 130:

[0889]

[0890] (E) and (Z)-4-(tert-butoxyimino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0891] Yellow solid, melting point: 221-223℃.

[0892] 1H NMR(500MHz,DMSO-d6)δ9.59(s,1H),9.10(dd,J=10.0Hz,1H),8.35(dd,J=5.0,1.5H z,1H),8.02-7.95(m,1H),7.91-7.85(m,1H),4.19(s,3H),4.15(s,3H),1.56(s,9H).

[0893] 13 C NMR(126MHz,DMSO-d6)δ174.19,143.95,137.64,135.39,134.97,132.32,1 31.49,131.12,127.59,126.94,125.70,85.60,39.44,36.44,27.70,27.65.

[0894] HRMS (ESI-TOF) m / z theoretical value: C 17 H 20 N3O2[MI] + ,298.1550, Measured value: 298.1551.

[0895] Compound 131:

[0896]

[0897] (E) and (Z)-4-((cyclopropylmethoxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0898] Yellow solid, melting point: 170-172℃.

[0899] 1 H NMR (400MHz, DMSO-d6) δ9.58(s,1H),9.09(dd,J=8.0,0.4Hz,1H),8.34(dd,J=8.0,1.6Hz,1H),8.03-7.95(m,1H),7.88(td,J =8.0,1.2Hz,1H),4.47(d,J=8.0Hz,2H),4.18(s,4H),4.13(s,3H),1.47-1.35(m,1H),0.70-0.62(m,2H),0.51-0.42(m,2H).

[0900] 13C NMR(101MHz,DMSO-d6)δ174.17,144.01,1310.08,135.38,134.48,132.46, 131.56,131.11,127.62,126.88,125.79,83.19,39.14,36.44,10.70,3.76.

[0901] HRMS (ESI-TOF) m / z theoretical value: C 17 H 18 N3O2[MI] + ,296.1394, Measured value: 296.1397.

[0902] Compound 132:

[0903]

[0904] (E) and (Z)-4-((allyloxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0905] Yellow solid, melting point: 139-141℃.

[0906] 1 H NMR (400MHz, DMSO-d6) δ9.57(s,1H),9.04(dd,J=8.0,1.2Hz,1H),8.34(dd,J=8.0,1.2Hz,1H),7.99(td,J=8.0,1.2Hz,1H),7.89( td,J=8.0,1.2Hz,1H),6.28-6.15(m,1H),5.58-5.50(m,1H),5.46-5.39(m,1H),5.12(d,J=8.0Hz,2H),4.18(s,3H),4.10(s,3H).

[0907] 13 C NMR(101MHz,DMSO-d6)δ174.16,144.07,138.48,135.41,134.38,133.51,13 2.59,131.66,131.13,127.67,126.74,125.88,120.67,79.10,39.17,36.44.

[0908] HRMS (ESI-TOF) m / z theoretical value: C 16 H 16 N3O2[MI] + ,282.1237, Measured value: 282.1239.

[0909] Compound 133:

[0910]

[0911] (E) and (Z)-4-(((4-methoxybenzyl)oxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0912] 1 H NMR (400MHz, DMSO-d6) δ9.54(s,1H),9.05(dd,J=10.0,0.8Hz,1H),8.32(dd,J=8.0,1.2Hz,1H),8.02-7.92(m,1H),7. 86(td,J=8.0,1.2Hz,1H),7.56-7.49(m,2H),7.03-6.95(m,2H),5.60(s,2H),4..16(s,3H),4.06(s,3H),3.77(s,3H).

[0913] 13 C NMR(101MHz,DMSO-d6)δ174.13,160.14,144.02,138.38,135.38,134.37,132.53,131.5 8,131.44,131.11,128.50,127.63,126.79,125.83,114.51,79.91,55.65,39.22,36.41.

[0914] HRMS (ESI-TOF) m / z theoretical value: C 21 H 20 N3O3[MI] + Measured value: 363.11499.

[0915] Compound 134:

[0916]

[0917] (E) and (Z)-4-(((4-chlorobenzyl)oxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0918] 1H NMR (400MHz, DMSO-d6) δ9.54(s,1H),9.07(dd,J=8.0,0.8Hz,1H),8.33(dd,J=8.0,1.6Hz,1H),8.01-.95(m,1 H),7.88(td,J=8.0,1.2Hz,1H),7.65-7.58(m,2H),7.55-7.48(m,2H),5.67(s,2H),4.16(s,3H),4.02(s,3H).

[0919] 13 C NMR(101MHz,DMSO-d6)δ174.14,144.05,138.81,135.74,135.43,134.25,133.88,13 2.66,131.75,131.41,131.16,129.19,127.68,126.73,125.93,78.99,39.17,36.41.

[0920] HRMS (ESI-TOF) m / z theoretical value: C 20 H 17 ClN3O2[MI] + ,366.1004, Measured value: 366.1006.

[0921] Compound 135:

[0922]

[0923] (E) and (Z)-1,3-dimethyl-9-oxo-4-(((4-(trifluoromethyl)benzyl)oxy)imino)-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0924] Yellow solid, melting point: 158-160℃.

[0925] 1 H NMR (400MHz, DMSO-d6) δ9.53(s,1H),9.11(dd,J=8.0,0.8Hz,1H),8.34(dd,J=8.0,0.8Hz,1H),7.99(td,J =8.0,1.6Hz,1H),7.89(td,J=8.0,1.2Hz,1H),7.86-7.76(m,4H),5.78(s,2H),4.16(s,3H),4.00(s,3H).

[0926] 13C NMR(101MHz,DMSO-d6)δ174.14,144.07,141.53,139.03,135.46,134.20,132.73,131.84,131.19,129 .63,129.32,127.71,126.72,126.11(126.08,126.04,126.00,J=4.0Hz),123.26,78.84,39.12,36.41.

[0927] HRMS (ESI-TOF) m / z theoretical value: C 21 H 17 F3N3O2[MI] + ,400.1267, Measured value: 400.1268.

[0928] Compound 136:

[0929]

[0930] (E) and (Z)-4-(((4-fluorobenzyl)oxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0931] Yellow solid, melting point: 175-177℃.

[0932] 1 H NMR (400MHz, DMSO-d6) δ9.54(s,1H),9.07(d,J=8.0Hz,1H),8.32(dd,J=8.0,1.2Hz,1H),7.97(td,J=8.0,1.6Hz ,1H),7.88(td,J=8.0,1.2Hz,1H),7.69-7.56(m,2H),7.35-7.24(m,2H),5.66(s,2H),4.16(s,3H),4.03(s,3H).

[0933] 13 C NMR(101MHz,DMSO-d6)δ174.14,163.99(161.55,J=244.0Hz),144.04,138.68,135.40,134.29,133.02(132.99,J=3.0Hz),13 2.62,131.98(131.89,J=9.0Hz),131.70,131.15,127.66,126.75,125.91,116.14(115.93,J=21.0Hz),79.14,39.18,36.41.

[0934] HRMS (ESI-TOF) m / z theoretical value: C 20 H 17 FN3O2[MI] + ,350.1299, Measured value: 350.1302.

[0935] Compound 137:

[0936]

[0937] (E) and (Z)-1,3-dimethyl-9-oxo-4-(((perfluorophenyl)methoxy)imino)-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0938] 1 H NMR (400MHz, DMSO-d6) δ9.54(s,1H),8.94(d,J=8.0Hz,1H),8.30(d,J=8.0Hz,1H) ,8.02-7.92(m,1H),7.87(t,J=8.0Hz,1H),5.78(s,2H),4.14(s,3H),4.03(s,3H).

[0939] 13 C NMR(126MHz,DMSO-d6)δ175.44,174.10,144.09,139.74,135.84,135.44,133.92,13 2.92,132.27,131.84,131.26,127.79,127.39,126.66,126.23,66.49,38.71,36.47.

[0940] HRMS (ESI-TOF) m / z theoretical value: C 20 H 13 F5N3O2[MI] + ,422.0922, Measured value: 422.0920.

[0941] Compound 138:

[0942]

[0943] (E) and (Z)-4-((benzyloxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-bromide

[0944] 1H NMR(500MHz,DMSO-d6)δ9.53(s,1H),9.08(dd,J=10.0,1.0Hz,1H),8.33(dd,J=10.0,1.0Hz,1H),8.01-7.93(m, 1H),7.88(td,J=10.0,1.0Hz,1H),7.60-7.55(m,2H),7.49-7.38(m,3H),5.68(s,2H),4.16(s,3H),4.03(s,3H).

[0945] 13 C NMR(126MHz,DMSO-d6)δ174.15,144.04,138.61,136.66,135.42,134.32,132.61,13 1.66,131.16,129.49,129.23,129.19,127.67,126.77,125.90,80.09,39.13,36.39.

[0946] HRMS (ESI-TOF) m / z theoretical value: C 20 H 18 N3O2[MI] + ,322.1394, Measured value: 322.1393.

[0947] Compound 139:

[0948]

[0949] (E) and (Z)-4-((benzyloxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-p-toluenesulfonate

[0950] 1 H NMR(500MHz,DMSO-d6)δ9.53(s,1H),9.08(dd,J=10.0,1.0Hz,1H),8.33(dd,J=10.0,1.0Hz,1H),8.01-7.93(m, 1H),7.88(td,J=10.0,1.0Hz,1H),7.60-7.55(m,2H),7.49-7.38(m,3H),5.68(s,2H),4.16(s,3H),4.03(s,3H).

[0951] 13C NMR(126MHz,DMSO-d6)δ174.15,144.04,138.61,136.66,135.42,134.32,132.61,13 1.66,131.16,129.49,129.23,129.19,127.67,126.77,125.90,80.09,39.13,36.39.

[0952] HRMS (ESI-TOF) m / z theoretical value: C 20 H 18 N3O2[MI] + ,322.1394, Measured value: 322.1393.

[0953] Compound 140:

[0954]

[0955] (E) and (Z)-4-((benzyloxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-sulfate dimethyl ester

[0956] 1 H NMR(500MHz,DMSO-d6)δ9.53(s,1H),9.08(dd,J=10.0,1.0Hz,1H),8.33(dd,J=10.0,1.0Hz,1H),8.01-7.93(m, 1H),7.88(td,J=10.0,1.0Hz,1H),7.60-7.55(m,2H),7.49-7.38(m,3H),5.68(s,2H),4.16(s,3H),4.03(s,3H).

[0957] 13 C NMR(126MHz,DMSO-d6)δ174.15,144.04,138.61,136.66,135.42,134.32,132.61,13 1.66,131.16,129.49,129.23,129.19,127.67,126.77,125.90,80.09,39.13,36.39.

[0958] HRMS (ESI-TOF) m / z theoretical value: C 20 H 18 N3O2[MI] + ,322.1394, Measured value: 322.1395.

[0959] Compound 141:

[0960]

[0961] (E) and (Z)-1,3-dimethyl-4-(((4-nitrobenzyl)oxy)imino)-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0962] 1 H NMR(500MHz,DMSO-d6)δ9.54(s,1H),9.11(d,J=10.0Hz,1H),8.35-8.28(m,3H),8.00(td,J=10.0,1.5 Hz,1H),7.90(td,J=10.0,1.0Hz,1H),7.84(d,J=10.0Hz,2H),5.83(s,2H),4.16(s,3H),3.98(s,3H).

[0963] 13 C NMR(126MHz,DMSO-d6)δ174.14,147.97,144.44,144.09,139.22,135.47,134.14,13 2.79,131.92,131.21,130.21,127.74,126.70,126.04,124.28,78.38,39.14,36.44.

[0964] HRMS (ESI-TOF) m / z theoretical value: C 20 H 17 N4O4[MI] + ,377.1244, Measured value: 377.1247.

[0965] Compound 142:

[0966]

[0967] (E) and (Z)-4-((phenoxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0968] 1H NMR (400MHz, DMSO-d6) δ9.62 (s, 3H), 9.56 (s, 1H), 9.07 (d, J = 8.0Hz, 1H), 8.35 (dd ,J=8.0,1.6Hz,1H),8.29(dd,J=8.0,1.2Hz,3H),8.18(dd,J=7.8,1.4Hz,3H),8.03 –7.95(m,1H),7.89(td,J=7.6,1.6Hz,4H),7.79(td,J=7.6,1.2Hz,3H),7.69–7.5 8(m,8H),7.49–7.36(m,12H),4.14(s,3H),4.13(s,6H),4.02(s,3H),4.00(s,6H).

[0969] HRMS (ESI-TOF) m / z theoretical value: C 20 H 18 N3O2[MI] + ,318.1237, Measured value: 318.1238.

[0970] Compound 143:

[0971]

[0972] (E)-4-(((1,3-dioxane-2-yl)methoxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0973] 1 H NMR (400MHz, DMSO-d6) δ9.56(s,1H),9.03(d,J=8.0Hz,1H),8.35(d,J=8.0Hz,1H),7.98(t,J=8.0Hz,1H),7.87( t,J=8.0Hz,1H),5.46(t,J=4.0Hz,2H),4.18(s,3H),4.06(s,3H),4.01(t,J=4.0Hz,2H),3.98(s,J=4.0Hz,2H).

[0974] HRMS (ESI-TOF) m / z theoretical value: C 20 H 18 N3O2[MI] + ,328.1292, Measured value: 328.1297.

[0975] Compound 144:

[0976]

[0977] (E)-4-((2-methoxyethoxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0978] 1 H NMR (400MHz, DMSO-d6) δ9.55(s,1H),9.02(d,J=8.0Hz,1H),8.32(d,J=8.0Hz,1H),7.96(t,J=8.0Hz,1H),7 .86(t,J=8.0Hz,1H),4.73(t,J=4.0Hz,2H),4.16(s,3H),4.11(s,3H),3.81(t,J=4.0Hz,2H),3.32(s,3H).

[0979] 13 C NMR(126MHz,DMSO-d6)δ174.17,144.02,138.40,135.39,134.38,132.57,1 31.62,131.14,127.65,126.78,125.88,77.73,70.56,58.77,39.12,36.45.

[0980] HRMS (ESI-TOF) m / z theoretical value: C 16 H 18 N3O3[MI] + ,300.1343, Measured value: 300.1347.

[0981] Compound 145:

[0982]

[0983] (E)-4-((2-(benzyloxy)ethoxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0984] 1 H NMR (400MHz, DMSO-d6) δ9.53(s,1H),9.04(d,J=8.0Hz,1H),8.32(d,J=8.0Hz,1H),7.94(t,J=8.0Hz,1H),7.87(t,J= 8.0Hz,1H),7.34-7.19(m,4H),4.76(t,J=4.0Hz,2H),4.56(s,2H),4.16(s,3H),4.03(s,3H),3.90(t,J=4.0Hz,2H).

[0985] 13 C NMR(126MHz,DMSO-d6)δ174.17,144.00,138.69,138.43,135.32,134.33,132.59,131.65,13 1.15,128.71,1210.04,127.98,127.65,126.79,125.87,77.75,72.48,68.19,39.03,36.46.

[0986] HRMS (ESI-TOF) m / z theoretical value: C 22 H 22 N3O3[MI] + ,376.1656, Measured value: 376.1656.

[0987] Compound 146:

[0988]

[0989] (E)-4-((2-(2-methoxyethoxy)ethoxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0990] 1 H NMR(400MHz, DMSO-d6)δ9.58(s,1H),9.07(dd,J=8.0,0.8Hz,1H),8.34(dd,J=8.0,1.2Hz,1H),8.00-7.93(m,1H),7.89(td,J=8.0 ,1.2Hz,1H),4.82-4.69(m,2H),4.18(s,3H),4.13(s,3H),3.95-3.86(m,2H),3.68-3.59(m,2H),3.53-3.44(m,2H),3.23(s,3H).

[0991] 13 C NMR(101MHz,DMSO-d6)δ174.17,144.01,138.40,135.34,134.37,132.57,131.68, 131.13,127.62,126.77,125.86,77.83,71.77,70.18,69.12,58.57,39.08,36.43.

[0992] HRMS (ESI-TOF) m / z theoretical value: C 18 H 22 N3O4[MI] +,344.1605, Measured value: 344.1609.

[0993] Compound 147:

[0994]

[0995] (E) and (Z)-4-((2-(2-(2-methoxyethoxy)ethoxy)ethoxy)imino)-1,3-dimethyl-9-oxo-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[0996] 1 H NMR (400MHz, DMSO-d6) δ9.63 (s, 1H), 9.56 (s, 1H), 9.02 (d, J = 8.0Hz, 1H), 8.34-8.09 (m, 3H), 8.01-7.70 (m, 4H), 4.78 -4.58(m,4H),4.21-4.01(m,11H),3.90-3.80(m,4H),3.63-3.42(m,10H),3.40-3.30(m,5H),3.16(d,J=12.0Hz,5H).

[0997] 13 C NMR (101MHz, DMSO) δ175.23,174.18,144.73,144.01,138.39,137.03,135.84,135 .36,134.81,133.19,132.56,131.67,131.13,131.03,130.53,129.74,128.12,127 .62,127.38,126.61,125.85,125.38,77.84,76.78,71.73,70.42,70.26,70.22,70.10,70.05,70.01,69.12,68.72,58.54,58.50,41.50,39.09,36.70,36.62,36.42.

[0998] HRMS (ESI-TOF) m / z theoretical value: C 20 H 26 N3O5[MI] + ,388.1867, Measured value: 388.1866.

[0999] Compound 148:

[1000]

[1001] (E) and (Z)-4-((benzyloxy)imino)-1-butyl-3-methyl-9-oxo-2-(3,4,5-trimethoxyphenyl)-4,9-dihydro-1H-naphthol[2,3-d]imidazol-3-iodide

[1002] 1 H NMR(400MHz, DMSO-d6)δ9.01(d,J=8.1Hz,1H),8.27(dd,J=7.8,1.6Hz,1H),8.17–8. 08(m,5H),7.93–7.89(m,1H),7.85–7.79(m,3H),7.72(t,J=7.4Hz,3H),7.54–7.47( m,7H),7.45-7.30(m,9H),5.64(s,2H),5.54(s,2H),5.53(s,3H),4.10(d,J=3.4Hz, 8H),4.02(s,2H),3.95(s,3H),3.84(s,6H),2.76(s,3H),2.75(s,5H),2.67(s,3H).

[1003] HRMS (ESI-TOF) m / z theoretical value: C 20 H 26 N3O5[MI] + ,540.2493, Measured value: 540.2495.

[1004] Compound 149:

[1005]

[1006] (E) and (Z)-4-((benzyloxy)imino)-1,3-dimethyl-11-oxo-4,11-dihydro-1H-anthracene[2,3-d]imidazol-3-iodide

[1007] 1 H NMR(400MHz,DMSO-d6)δ9.67(s,1H),9.60(s,1H),9.54(s,1H),8.88(s,1H),8.82(s,1H),8.74(s,1H),8.31–8.13(m,4H), 7.84–7.68(m,4H),7.68-7.55(m,4H),7.51–7.38(m,6H),5.71(s,2H),5.61(s,2H),4.17(m,6H),4.02(s,3H),4.00(s,3H).

[1008] 13C NMR(101MHz,DMSO-d6)δ174.07,144.77,144.17,138.54,137.03,136.19,135.13,135.08,133.61,132.73,130.69,130.54,130.41,130.37 ,130.17,130.10,129.85,129.75,129.40,129.26,129.23,129.17,12 9.13,129.04,128.92,128.47,126.26,125.23,122.71,79.71,78.95.

[1009] HRMS (ESI-TOF) m / z theoretical value: C 20 H 26 N3O5[MI] + ,382.1550, Measured value: 382.1555.

[1010] Compound 150:

[1011]

[1012] (E) and (Z)-4-((allyloxy)imino)-1,3-dimethyl-11-oxo-4,11-dihydro-1H-anthracene[2,3-d]imidazol-3-iodide

[1013] 1 H NMR (400MHz, DMSO-d6) δ9.67(s,2H),9.58(s,2H),8.98(s,2H),8.87(s,1H),8.75(s,1H),8.38–8.34(m,2H),8.23(dd,J=6.4,2.8Hz,3H),7.8 7–7.79(m,5H),6.32–6.17(m,5H),5.18(dt,J=5.8,1.2Hz,3H),5.07(d,J=6.0Hz,2H),4.23–4.20(m,5H),4.20(s,3H),4.11(d,J=1.6Hz,8H).

[1014] HRMS (ESI-TOF) m / z theoretical value: C 20 H 26 N3O5[MI] + ,332.1334, Measured value: 332.1335.

[1015] Compound 151:

[1016]

[1017] (E) and (Z)-1,3-dimethyl-4-(((4-nitrobenzyl)oxy)imino)-11-oxo-4,11-dihydro-1H-anthracene[2,3-d]imidazol-3-iodide

[1018] 1 H NMR (400MHz, DMSO-d6) δ9.74(s,1H),9.53(s,1H),8.94(s,1H),8.34–8.24(m,5H),7.86–7.79(m,3H),5.86(s,2H),4.18(s,3H),3.97(s,3H).

[1019] HRMS (ESI-TOF) m / z theoretical value: C 20 H 26 N3O5[MI] + ,427.1401, Measured value: 427.1405.

[1020] The compounds obtained by the methods described in Examples 1-10 can all be used to obtain the final imidazolium biomolecules in Examples 11-13. Furthermore, other similar quinone oxime imidazolium derivatives and their synthetic intermediates can be readily prepared using the methods described in the above examples or preparation methods, or using some variations that are readily apparent to those skilled in the art.

[1021] The effects of the compounds of the present invention were confirmed in the following experiments.

[1022] Experimental Example 1: In vitro cancer cell proliferation inhibition assay

[1023] Experimental Methods: Pancreatic cancer cells CFPAC-1 were cultured in Dalbeco-modified Eagle medium supplemented with 10% FBS and 5% penicillin antibiotics. CFPAC-1 cancer cells were seeded in 96-well plates and incubated for 24 hours. The following day, various concentrations (100, 20, 10, 1, 0.1, 0.01, 0, 001 μM) of the test compound and positive control drug were added to each well, while the blank control was added with the corresponding volume of fresh medium. Cell proliferation was evaluated by MTT assay after 24 or 48 hours.

[1024] Experimental results: The compound of the present invention effectively inhibited the proliferation of cancer cells, with a half-maximal lethal concentration (IC50) of 1 / 3. 50 The value is below 1 μM, and the best compound can reach below 10 nM.

[1025]

[1026]

[1027]

[1028] In addition, compounds (I), (II), (III) and (IV) of this invention exhibit good inhibitory activity against the proliferation of other cancer cells, including non-small cell lung cancer cells (H460, H1299), liver cancer cells (HepG2), rectal cancer cells (HT29), leukemia cells (CCRF-CEM), prostate cancer cells (PC-3), ovarian cancer cells (SKOV-3), melanoma cells (A375), myeloma cells (RPMI-8226), esophageal cancer cells (TE-1), pancreatic cancer cells (CFPAC-1, PANC-1, SW1990, ASPC-1, BXPC-3), bladder cancer cells (5637), and gastric cancer cells (KATO-III). The results are as follows:

[1029]

[1030]

[1031] Experimental Example 2: In vivo cancer cell proliferation inhibition experiment

[1032] Experimental method: 3×10 7 CFPAC-1 pancreatic cancer cells were transplanted subcutaneously into the axillae of Balb / c nude mice. Drug administration began when the tumor volume reached 50-100 mm³, 100-200 mm³, and greater than 200 mm³, respectively, every three days for a total of seven doses, at a dose of 7 mg / kg. The control group received saline injections. Before each administration, the tumor diameter and weight of the mice were measured using a diaphragm until the day after the final administration. The tumor volume was calculated using the following formula.

[1033] Tumor volume (mm) 3 = 1 / 2 × [minor diameter (mm)] 2 × Major axis (mm)

[1034] Experimental Results: In this experiment, compounds (III) and (IV) of the present invention effectively inhibited the proliferation of cancer cells. For example, Examples 123, 124, 125 and 128 showed 100% inhibitory activity of proliferation compared with the positive control group at a dose of 7 mg / kg. Compounds 121, 132, 137, 138, 139, 140, 143, 144, 145, 146 and 147 showed inhibition rates of over 80% and obvious dose dependence.

[1035] The compounds of this invention also showed a good inhibitory effect on cancer cell proliferation in animal models in which other cancer cells (non-small cell lung cancer A549) were transplanted.

[1036] Test Example 3: Compound Toxicity Test

[1037] Experimental method: Compounds 121, 123, 124, 125, 128, 132, 137, 138, 139, 140, 143, 144, 145, 146, and 147 of the present invention were administered via tail vein injection at a dose of 5 mg / kg daily for 7 consecutive days, and the weight changes of balb / c mice were monitored.

[1038] Experimental results: The mice did not show a significant decrease in body weight and were in good condition, but the gemcitabine-treated mice in the positive control group showed a significant decrease in body weight and were lethargic.

[1039] Experimental Example 4: Antiviral Activity

[1040] Experimental Methods: Weigh 4.59 mg of compound 125 into a 15 ml centrifuge tube, add 10 ml of sterile water, vortex to dissolve, and continue vortexing until no obvious yellow particles are visible. Aliquot and store at -20℃, 200 μl per vial, concentration 1 mM. Weigh 2.79 mg of cidofovir (molecular weight 279) into a 15 ml centrifuge tube, add 10 ml of sterile water to dissolve, aliquot and store at -20℃, 200 μl per vial, concentration 1 mM.

[1041] Pockmark test:

[1042] 1. Seed 293A cells into 24-well plates, 150,000 cells per well, and incubate at 37°C for 12-24 hours. Use the cells for experiments when they reach 90% confluence.

[1043] 2. Melt 2% low-melting-point agarose gel and place it in a 56°C water bath for later use.

[1044] 3. The titer is 10... 9 TCID 50 / mL of adenovirus diluted 10 5 Discard the culture medium in the 24-well plate, add 200 μl of virus dilution to each well, and incubate at 37°C in a 5% CO2 incubator, shaking once every 30 minutes, for a total of 1 hour.

[1045] 4. Perform serial dilutions of the test drug compound 125 and cidofovir using 2x MEM (add 16 μl of compound 125 to 8 ml of 2x MEM, vortex to mix, take 4 ml of the mixture and add it to a new 4 ml of 2x MEM, mix well, and so on, to make 5 dilutions of 2 μM, 1 μM, 500 nM, 250 nM, and 125 nM; the highest concentration of compound 125 is 1 μM; similarly, add 400 μl of cidofovir to 7.6 ml of 2x MEM, vortex to mix, take 4 ml of the mixture and add it to a new 4 ml of 2x MEM, mix well, and so on, to make 5 dilutions of 50 μM, 25 μM, 12.5 μM, 6.25 μM, and 3.125 μM), and store at 37°C for later use.

[1046] 4. Discard the virus solution, add an equal volume of preheated (56°C) agarose gel to 2xMEM, mix well, add 2 ml to each well, and incubate at room temperature for 30 min (gel).

[1047] 5. Incubate at 37℃, and observe virus replication using a fluorescence microscope during the incubation period.

[1048] Experimental results: After 4 days, numerous non-CPE-formed white spots were observed in the cidofovir group, and after 5 days, non-CPE-formed white spots also appeared in the low-concentration compound 127 group. Compound 125 inhibited viral replication with a significant dose-dependent inhibitory effect.

[1049] The specific embodiments of the present invention have been described above. It should be understood that the present invention is not limited to the specific embodiments described above, and those skilled in the art can make various modifications or variations within the scope of the claims, which do not affect the essence of the present invention.

Claims

1. A fused quinone oxime imidazoline derivative, the structure of which is represented by the following general formula (I) or (II): （Ⅰ） （Ⅱ）； in, Ring A: Selected from benzene rings, naphthalene rings, or NO2-substituted benzene rings; R 1 Selected from -hydrogen atom, -C1 to C6 straight-chain alkyl or branched alkyl, -benzyl, phenyl, halogen-substituted phenyl, -C4 to C6 methylcycloalkyl, -C3 to C6 alkenyl or -CH2CH(OCH2CH2O); or selected from -CH2(C6H 5-m -X m ), where m = 1 to 5, and X is a halogen atom, NO2, hydrogen atom, or -OC. n H 2n+1 n=1~6; or selected from -CH2(C6H4-CH n X 3-n ), where n=1~3, X is a halogen atom; or selected from -(C n H 2n -O) y -C m H 2m+1 Where n = 1–6, m = 1–6, y = 1–3; or selected from -C n H 2n -OC m H 2m -Ph, where n=1~6, m=1~6; or selected from -C n H 2n -NH2, where n=1~6; or selected from -CH2-heteroaryl, wherein the heteroaryl refers to a 5-6 member monocyclic heteroaryl having 1-4 heteroatoms selected from one or more of N, S, and O; R 2 Selected from hydrogen atoms or C1-C6 chain alkyl groups; R 3 Selected from -hydrogen atom, -C1 to C6 straight-chain alkyl or branched-chain alkyl, -C4 to C6 methylcycloalkyl, -phenyl, or C1 to C6 alkyl-substituted phenyl; or selected from, -OR a and / or halogen-substituted phenyl, R a It is an alkyl group with a -C1 to C6 chain; R 4 The following are selected from -hydrogen atom, -C1 to C6 straight-chain alkyl or branched alkyl, -C3 to C6 methylcycloalkyl, -C1 to C6 alkylene-O-C1 to C6 alkyl, -C3 to C6 alkenyl, -benzyl or substituted benzyl, -phenyl or substituted phenyl, or -CH2-thiophene; or selected from -CH2-heteroaryl, wherein the heteroaryl refers to a 5-6 member monocyclic heteroaryl having 1-4 heteroatoms selected from one or more of N, S, and O; Furthermore, R 4 The substituents are selected from -CN, C1-C6 alkyl groups, halogens, or OR. a R a It is an alkyl group with a chain length of -C1 to C6; halogenated substituted phenyl groups are monosubstituted; X - Counter anions are selected from halide ions, sulfonate ions, acetate ions, trifluoroacetate ions, carbonate ions, and sulfate ions; when the anion on the substituent forms an inner salt with the imidazolium cation, X - It does not exist.

2. A fused quinone oxime imidazole derivative and its hydrochloride, the structure of which is represented by the following general formulas (III) and (IV): （Ⅲ） （Ⅳ）； in, Ring A: Selected from benzene rings, naphthalene rings, or NO2-substituted benzene rings; R 1 Selected from -hydrogen atom, -C1 to C6 straight-chain alkyl or branched alkyl, -benzyl, phenyl, halogen-substituted phenyl, -C3 to C6 methylcycloalkyl, -C3 to C6 alkenyl or -CH2CH(-OCH2CH2O-); or selected from -CH2(C6H 5-m -X m ), where m = 1 to 5, and X is a halogen atom, NO2, hydrogen atom, or -OC. n H 2n+1 n=1~6; or selected from -CH2(C6H4-CH n X 3-n ), where n=1~3, X is a halogen atom; or selected from -(C n H 2n -O) y -C m H 2m+1 Where n = 1–6, m = 1–6, y = 1–3; or selected from -C n H 2n -OC m H 2m -Ph, where n=1~6, m=1~6; or selected from -C n H 2n -NH2, where n=1~6; or selected from -CH2-heteroaryl, wherein the heteroaryl refers to a 5-6 member monocyclic heteroaryl having 1-4 heteroatoms selected from one or more of N, S, and O; R 3 Selected from -hydrogen atom, -C1 to C6 straight-chain alkyl or branched-chain alkyl, -C4 to C6 methylcycloalkyl, -phenyl, or C1 to C6 alkyl-substituted phenyl; or selected from, -OR a and / or halogen-substituted phenyl, R a It is an alkyl group with a -C1 to C6 chain; R 4 Selected from -hydrogen atom, -C1 to C6 straight-chain alkyl or branched alkyl, -C3 to C6 methylcycloalkyl, -C1 to C6 alkylene, -C1 to C6 alkyl, -C3 to C6 alkenyl, -benzyl or substituted benzyl, -phenyl or substituted phenyl, -CH2-thiophene or -(C n H 2n -O) y -C m H 2m+1 Where n=1~6, m=1~6, y=1~3; or selected from -CH2-heteroaryl, wherein the heteroaryl refers to a 5-6 member monocyclic heteroaryl having 1-4 heteroatoms selected from one or more of N, S, and O; Furthermore, R 4 The substituents are selected from -CN, C1-C6 alkyl groups, halogens, or OR. a R a It is an alkyl group with a chain length of -C1 to C6; halogenated phenyl groups are monosubstituted.

3. A pharmaceutical composition comprising one or more quinone oxime-imidazole derivatives as described in claim 1 and a pharmaceutically permissible carrier.

4. A pharmaceutical composition comprising one or more fused quinone oxime imidazole derivatives or their hydrochloride salts as described in claim 2, and a pharmaceutically permissible carrier.

5. Use of a pharmaceutical composition according to claim 3 or 4 in the preparation of an anticancer drug; wherein the anticancer drug is a drug for treating non-small cell lung cancer, breast cancer, liver cancer, rectal cancer, leukemia, prostate cancer, ovarian cancer, melanoma, myeloma, esophageal cancer, pancreatic cancer, bladder cancer, or gastric cancer.

6. Use of a pharmaceutical composition according to claim 3 or 4 in the preparation of an anti-cervical cancer drug; wherein, in the quinone oxime-imidazolium derivative, quinone oxime-imidazolium derivative, or its hydrochloride salt, R... 4 Selected from -hydrogen atom, -C1 to C6 straight-chain alkyl or branched alkyl, -C3 to C6 methylcycloalkyl, -C1 to C6 alkylene, -C1 to C6 alkyl, -C3 to C6 alkenyl, -benzyl or substituted benzyl, -phenyl or substituted phenyl, or -CH2-thiophene.

7. Use of a pharmaceutical composition in the preparation of an antiviral drug, said pharmaceutical composition comprising a quinone oxime-imidazole derivative and a pharmaceutically permissible carrier; said quinone oxime-imidazole derivative having the following structural formula: or .

8. A method for preparing the fused quinone oxime imidazole derivative according to claim 2, characterized in that, The method includes the following steps: A. Substituted quinone imidazole derivatives using proton solvents (V), and R 1 ONH2•HCl reacts with a weak base or with the corresponding R under the catalysis of a weak base. 1 ONH2 undergoes an oxime reaction in the presence of a weak base hydrochloride to yield a quinone oxime imidazole derivative. (III) and (Ⅳ).

9. A method for preparing the fused quinone oxime imidazoline derivative according to claim 1, characterized in that, The method includes the following steps: A. Substituted quinone imidazole derivatives using proton solvents (V), and R 1 ONH2•HCl reacts with a weak base or with the corresponding R under the catalysis of a weak base. 1 ONH2 undergoes an oxime reaction in the presence of a weak base hydrochloride to yield a quinone oxime imidazole derivative. (III) and (Ⅳ); B. Quinoxime imidazole derivatives (III) or (IV) in an organic solvent with the corresponding halogenated reagent R 2 X undergoes an N-alkylation reaction to yield quinone oxime imidazoline derivatives (I) or (II).

10. The preparation method according to claim 9, characterized in that, In step A, the quinone imidazole derivative (V), R 1 The molar ratio of ONH2•HCl to the weak base is 1:1.2~5:0.001~0.

01. The protic solvent is selected from methanol, ethanol, and isopropanol. The weak base is selected from pyridine, triethylamine, and potassium carbonate. The reaction temperature is 90~125 ℃ and the reaction time is 12~48 hours.

11. The preparation method according to claim 9, characterized in that, In step B, the quinone oxime imidazole derivative (III) or (IV) and the halogenated reagent R 2 The molar ratio of X is 1:1 to 1:100, the solvent is selected from acetonitrile, ethyl acetate, and tetrahydrofuran, the reaction temperature is 50 to 120 °C, and the reaction time is 8 to 48 hours.

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