Imidazoquinoline or benzoindazolone compounds and their production intermediates

Abstract

The present invention relates to imidazoquinoline or benzindazolone compounds, their pharmaceutically acceptable salts, hydrates, solvates, enantiomers, partial stereoisomers, tautomers, or precursor drugs, their uses in the prevention and treatment of inflammatory diseases, and intermediates for their preparation. The compounds of the present invention can be used as substrates for NQO1 to activate the redox reaction of NQO1, thereby enabling the suppression of the expression and activity of inflammatory cytokines, and can therefore be used for the prevention or treatment of diseases associated with NQO1 activity.

Description

[Technical field]

[0001] The present invention relates to imidazoquinoline or benzoindazolone compounds, their use in the prevention or treatment of inflammatory diseases, and intermediates for the preparation thereof. [Background technology]

[0002] The human immune system has developed a variety of defense mechanisms to protect the body from both internal and external threats. The functions of the immune system can be divided into immune response, which promotes immunity, and immune tolerance, which suppresses excessive immune response. Maintaining an appropriate balance between these two immune functions is called immune homeostasis, which is extremely important for maintaining health.

[0003] However, immune function can become unbalanced due to various internal and external factors. When the immune response is stronger than immune tolerance, i.e., when immune cells are excessively activated, inflammatory diseases and autoimmune diseases can occur. Conversely, when immune tolerance is stronger than the immune response, i.e., when the immune system does not function normally, it can lead to diseases such as infectious diseases and cancer. Therefore, there are attempts to treat various immune-related diseases through maintaining homeostasis of the immune system, which maintains a balance between immune response activation and suppression.

[0004] Among inflammatory diseases, ulcerative colitis is an inflammatory bowel disease in which inflammation or ulcers occur in the large intestine due to genetic factors or an excessive immune response. Common symptoms include severe abdominal pain, weight loss, bleeding, and diarrhea or stools containing blood and mucus. In many cases, the condition worsens and improves repeatedly, or progresses to other complications or colon cancer. Although research into ulcerative colitis is actively being conducted, a completely curative treatment has not yet been developed, and anti-inflammatory drugs and corticosteroids are commonly used, with immunosuppressants, steroids, and antibiotics being used depending on the patient's condition. It can be cured by surgery, but drug therapy is recommended over surgery due to the complexity of the surgery and the significant side effects from aftereffects.

[0005] Autoimmune diseases are diseases caused by an imbalance in which the immune system becomes overactive and attacks healthy cells. Typical examples include rheumatoid arthritis, type 1 diabetes, inflammatory bowel disease, and atopic dermatitis.

[0006] The human body possesses various types of immune suppressor cells to suppress autoimmune diseases or reduce excessive immune responses and maintain immune homeostasis. Among these, macrophages are extremely important immune cells responsible for innate immunity and are distributed in various forms throughout all tissues of the human body.

[0007] Under normal conditions, macrophages protect the body by destroying external antigens through phagocytosis and secreting toxins. Macrophages also play a very diverse role in immune responses, such as wound healing and inflammatory responses in the human body. Macrophages are traditionally divided into M1 and M2 phenotypes depending on pathological conditions. However, recent research trends have revealed that macrophages have a variety of phenotypes depending on their origin, location, microenvironment, and pathological conditions, rather than this traditional dichotomous classification (Nature Immunology 2016(17),34,Am J Physiol Gastrointest Liver Physiol 2016(311),G59). Proinflammatory macrophages, which are M1 phenotype, are activated by lipopolysaccharides (LPS) or tumor necrosis factor alpha (TNF-α) and secrete IL-1β, IL-6, TNF-α, etc., and their main metabolic pathway is glycolysis in the cytoplasm rather than mitochondria. On the other hand, the main metabolic pathway of M2 phenotype macrophages is oxidative phosphorylation of mitochondria, and they are activated by IL-4 or IL-10, etc., and mainly play an important role in alleviating inflammation and wound healing (Frontiers in immunology 2017, 61).

[0008] When NAD(P)H quinone oxidoreductase 1 (NQO1) is activated in vivo, NAD + and NAD + The / NADH ratio increases, causing changes in cellular metabolism through mitochondrial activation, inducing macrophage cellular metabolism toward mitochondrial oxidative phosphorylation rather than glycolysis. This has been reported to polarize macrophages to an anti-inflammatory macrophage phenotype (M2 phenotype), thereby suppressing the expression and activity of inflammatory cytokines (Frontiers in Immunology 2017, 289). Summary of the Invention [Problem to be solved by the invention]

[0009] An object of the present invention is to provide a novel imidazoquinoline or benzoindazolone compound, or a pharma- ceutically acceptable salt, hydrate, solvate, enantiomer, partial stereoisomer, tautomer or precursor drug thereof, which exhibits a preventive or therapeutic effect on inflammatory diseases; and a preparation intermediate thereof. [Means for solving the problem]

[0010] The inventors of the present invention experimentally confirmed that novel imidazoquinoline or benzoindazolone compounds can be used as substrates for NQO1 to facilitate the redox reaction of NQO1, thereby enhancing the NAD + and NAD + The present invention has been completed by revealing that the increase in the NADH / NADH ratio can be used to prevent or treat inflammatory diseases by causing changes in cellular metabolism through mitochondrial activation.

[0011] Accordingly, a first aspect of the present invention relates to a compound represented by the following formula 1, or a pharma- ceutically acceptable salt, hydrate, solvate, enantiomer, partial stereoisomer, tautomer, or prodrug thereof:

[0012] [ka]

[0013] During the ceremony, R1 is H, halo, substituted or unsubstituted C 1-6 Alkyl, substituted or unsubstituted C 1-6 Alkyloxy, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 selected from the group consisting of aryl, substituted or unsubstituted heteroaryl, nitro, cyano, -C(O)R5, -C(O)OR5, -C(O)NR6R7 and -NR6R7; R2, R3 and R4 are each independently absent, H, halo, substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 2-10 Alkenyl, substituted or unsubstituted C 2-10 Alkynyl, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 selected from the group consisting of aryl, substituted or unsubstituted heteroaryl, -C(O)R5, -C(O)OR5, -C(O)NR6R7, -S(O)(O)R5 and -S(O)(O)NR6R7; Two of X1, X2, X3, and X4 are carbon atoms (C) and the remaining two are nitrogen atoms (N), and X1 and X3 are not both N or X2 and X4 are not both N; [ka] is a single bond or a double bond depending on R1, R2, R3, X1, X2, X3 and X4, [ka] is absent or a single bond by X1, X2, X3 and X4; The alkyl may be linear, branched or cyclic and may contain one or more double or triple bonds within the chain, and when substituted, the substituents may include halo, C 1-6 Alkyloxy, cyano, nitro, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 selected from the group consisting of aryl, heteroaryl, -C(O)R5, -C(O)OR5, -C(O)NR6R7 and -NR6R7; When the heterocyclyl, aryl or heteroaryl is substituted, the substituent is each selected from the group consisting of: 1-6 Alkyl, C 1-6 Alkyloxy, halo, cyano, nitro, -C(O)R5, -C(O)OR5, -C(O)NR6R7, -NR6R7, and C substituted with 1, 2 or 3 halo. 1-6selected from the group consisting of alkyl, R5 is H, C 1-6 Alkyl, substituted or unsubstituted C 2-5 selected from the group consisting of heterocyclyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; R6 and R7 are each independently H, C 1-6 selected from the group consisting of alkyl, heterocyclyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; or R6 and R7 may be bonded together to form a heterocyclyl containing at least one nitrogen (N) atom in the ring, with or without one or more further heteroatoms selected from N, O, and S; The aryl is C 6-10 The heterocyclyl is a 3- to 7-membered ring group having one or more heteroatoms selected from N, O, and S in the ring, and the heteroaryl is a 5- to 10-membered heteroaromatic ring group having one or more heteroatoms selected from N, O, and S in the ring.

[0014] A second aspect of the present invention relates to a compound represented by Chemical Formula 2, which is a preparation intermediate of the compound of Chemical Formula 1, or a salt, enantiomer, partial stereoisomer or tautomer thereof:

[0015] [ka]

[0016] In the formula, R1, R2, R3, R4, X2, X3, X4, [ka] and [ka] is as defined in formula 1, and R8 is a protecting group for a conventional hydroxy group known in the art. Effect of the Invention

[0017] The present invention provides novel imidazoquinoline or benzoindazolone compounds and their preparation intermediates.

[0018] The degree of reduction of cytochrome C was measured, and it was confirmed that the compound of the present invention was used as an efficient substrate for NQO1. The improved redox activity of NQO1 by the compound of the present invention was + and NAD + By increasing the β-aminobutyric acid / NADH ratio and causing changes in cellular metabolism through mitochondrial activation, it is possible to suppress the expression and activity of inflammatory cytokines. Therefore, it is expected that the compound of the present invention can be developed as a drug for the prevention or treatment of inflammatory diseases. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0019] Definition of Terms The terms used in this specification will be briefly explained.

[0020] The term "pharmaceutical acceptable salt" refers to a salt form of a compound that does not induce significant irritation to an organism to which the compound is administered and does not impair the biological activity and physical properties of the compound.

[0021] The terms "hydrates," "solvates," "prodrugs," "tautomers," "enantiomers," and "partial stereoisomers" also refer to forms of a compound that do not induce significant irritation to the organism to which the compound is administered and that do not impair the biological activity and physical properties of the compound.

[0022] The "pharmaceutically acceptable salt" includes acid addition salts formed by addition of inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, hydrobromic acid, hydroiodic acid, etc., or organic acids such as tartaric acid, formic acid, citric acid, acetic acid, trichloroacetic acid, fluoroacetic acid, gluconic acid, benzoic acid, lactic acid, fumaric acid, maleic acid, salicylic acid, methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, etc. When a carboxylic acid group is present in the compound of Chemical Formula 1, examples of pharmaceutically acceptable carboxylic acid salts include metal salts or alkaline earth metal salts formed with lithium, sodium, potassium, calcium, magnesium, etc., amino acid salts such as lysine, arginine, guanidine, etc., organic salts formed with dicyclohexylamine, N-methyl-D-glucamine, tris(hydroxymethyl)methylamine, diethanolamine, choline, triethylamine, etc. The compound of Chemical Formula 1 according to the present invention can be converted into its salt by a conventional method.

[0023] The term "hydrate" means a compound of the present invention or a salt thereof that contains a stoichiometric or non-stoichiometric amount of water bound by non-covalent intermolecular forces.

[0024] The term "solvate" refers to a compound of the present invention or a salt thereof that contains a stoichiometric or non-stoichiometric amount of a solvent bound by non-covalent intermolecular forces. The solvent for the solvate may be any solvent that is volatile, non-toxic, and / or suitable for administration to humans.

[0025] The term "prodrug" refers to a substance that can be converted in vivo to a compound of formula 1 according to the present invention. Prodrugs are often used because in some cases they are easier to administer than the parent drug. For example, they may be able to obtain bioactivity by oral administration, whereas the parent drug may not. Prodrugs may also have improved solubility in pharmaceutical dosage forms compared to the parent drug. For example, the prodrug may be in the form of an ester ("prodrug") that facilitates passage through cell membranes, where aqueous solubility is detrimental to mobility, but is metabolically hydrolyzed to the active carboxylic acid within the cell, where aqueous solubility is advantageous. Yet another example of a prodrug may be a short peptide (polyamino acid) bound to an acid group that is metabolically converted so that the peptide represents the active site.

[0026] The term "tautomer" refers to a type of structural isomer that has the same chemical or molecular formula but differs in the way the constituent atoms are connected, and the structure changes while alternating between both isomers, for example, a keto-enol structure.

[0027] The term "enantiomer" or "partial stereoisomer" refers to an isomer that has the same chemical or molecular formula but results from a change in the spatial arrangement of atoms in a molecule, with the term "enantiomer" meaning an isomer that is not superimposable as its mirror image, like the relationship between a right hand and a left hand, and "partial stereoisomer" meaning a stereoisomer that is not a mirror image. All of these isomers and mixtures thereof are within the scope of the present invention.

[0028] The term "alkyl" refers to straight-chain, branched and cyclic aliphatic hydrocarbon groups, and includes both "saturated alkyls" and "unsaturated alkyls" that have at least one double or triple bond site within the chain.

[0029] The term "aryl" refers to 6-10An aromatic ring group, "heterocyclyl" refers to a 3- to 7-membered ring group having one or more heteroatoms selected from nitrogen (N), oxygen (O), and sulfur (S) atoms in the ring, and "heteroaryl" refers to a 5- to 10-membered heteroaromatic ring group having one or more heteroatoms selected from nitrogen (N), oxygen (O), and sulfur (S) atoms in the ring.

[0030] The present invention will be described in detail below.

[0031] A first aspect of the present invention relates to a compound represented by the following formula 1, or a pharma- ceutically acceptable salt, hydrate, solvate, enantiomer, partial stereoisomer, tautomer, or prodrug thereof:

[0032] [ka]

[0033] During the ceremony, R1 is H, halo, substituted or unsubstituted C 1-6 Alkyl, substituted or unsubstituted C 1-6 Alkyloxy, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 selected from the group consisting of aryl, substituted or unsubstituted heteroaryl, nitro, cyano, -C(O)R5, -C(O)OR5, -C(O)NR6R7 and -NR6R7; R2, R3 and R4 are each independently absent, H, halo, substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 2-10 Alkenyl, substituted or unsubstituted C 2-10 Alkynyl, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 selected from the group consisting of aryl, substituted or unsubstituted heteroaryl, -C(O)R5, -C(O)OR5, -C(O)NR6R7, -S(O)(O)R5 and -S(O)(O)NR6R7; Two of X1, X2, X3, and X4 are carbon atoms (C) and the remaining two are nitrogen atoms (N), and X1 and X3 are not both N, or X2 and X4 are not both N; [ka] is a single bond or a double bond depending on R1, R2, R3, X1, X2, X3 and X4, [ka] is absent or a single bond by X1, X2, X3 and X4; The alkyl may be linear, branched or cyclic and may contain one or more double or triple bonds within the chain, and when substituted, the substituents may include halo, C 1-6 Alkyloxy, cyano, nitro, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 selected from the group consisting of aryl, substituted or unsubstituted heteroaryl, -C(O)R5, -C(O)OR5, -C(O)NR6R7 and -NR6R7; When the heterocyclyl, aryl or heteroaryl is substituted, the substituent is each selected from the group consisting of: 1-6 Alkyl, C 1-6 Alkyloxy, halo, cyano, nitro, -C(O)R5, -C(O)OR5, -C(O)NR6R7, -NR6R7, and C substituted with 1, 2 or 3 halo. 1-6 selected from the group consisting of alkyl, R5 is H, C 1-6 Alkyl, substituted or unsubstituted C 2-5 selected from the group consisting of heterocyclyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; R6 and R7 are each independently H, C 1-6selected from the group consisting of alkyl, heterocyclyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; or R6 and R7 may be bonded together to form a heterocyclyl containing at least one nitrogen (N) atom in the ring, with or without one or more further heteroatoms selected from N, O, and S; The aryl is C 6-10 The heterocyclyl is a 3- to 7-membered ring group having one or more heteroatoms selected from N, O, and S in the ring, and the heteroaryl is a 5- to 10-membered heteroaromatic ring group having one or more heteroatoms selected from N, O, and S in the ring.

[0034] The compounds of Formula 1 according to the present invention include compounds in which X2 and X3 are carbon atoms (C) and X1 and X4 are nitrogen atoms (N). In these compounds, R1 is as defined in Formula 1 and R2 is H, unsubstituted C, 1-10 Alkyl, and substituted or unsubstituted C 6-10 aryl, R3 is selected from the group consisting of H, -C(O)OR5 and -C(O)NR6R7, R4 is absent, and R5 is C 1-6 alkyl, and R and R are each independently H or C 1-6 It can be alkyl.

[0035] The compound of Formula 1 according to the present invention includes compounds in which X1 and X4 are carbon atoms (C), and X2 and X3 are nitrogen atoms (N).

[0036] In the present invention, a first specific example of the compound in which X1 and X4 in Chemical Formula 1 are carbon atoms (C) and X2 and X3 are nitrogen atoms (N) is: R2 is absent, H, halo, substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 2-10 Alkenyl, substituted or unsubstituted C 2-10 Alkynyl, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10and selected from the group consisting of aryl, substituted or unsubstituted heteroaryl, -C(O)R5, -C(O)OR5, -C(O)NR6R7, -S(O)(O)R5 and -S(O)(O)NR6R7, where when alkyl is substituted, the substituent is selected from the group consisting of halo, C 1-6 and when the heterocyclyl, aryl or heteroaryl is substituted, the substituent is selected from the group consisting of alkyloxy, cyano, nitro, -C(O)R5, -C(O)OR5, -C(O)NR6R7 and -NR6R7, 1-6 Alkyl, C 1-6 Alkyloxy, halo, cyano, nitro, -C(O)R5, -C(O)OR5, -C(O)NR6R7, -NR6R7, and C substituted with 1, 2 or 3 halo. 1-6 Selected from the group consisting of alkyl; R3 is absent, H, halo, substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 2-10 Alkenyl, substituted or unsubstituted C 2-10 Alkynyl, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 and selected from the group consisting of aryl, substituted or unsubstituted heteroaryl, -C(O)R5, -C(O)OR5, -C(O)NR6R7, -S(O)(O)R5 and -S(O)(O)NR6R7, where when alkyl is substituted, the substituent is selected from the group consisting of halo, C 1-6 Alkyloxy, cyano, nitro, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 selected from the group consisting of aryl, heteroaryl, -C(O)R5, -C(O)OR5, -C(O)NR6R7 and -NR6R7, where if heterocyclyl, aryl or heteroaryl is substituted, the substituent is each selected from the group consisting of: 1-6 Alkyl, C 1-6 Alkyloxy, halo, cyano, nitro, -C(O)R5, -C(O)OR5, -C(O)NR6R7, -NR6R7, and C substituted with 1, 2 or 3 halo. 1-6 Selected from the group consisting of alkyl; R4 is H, halo, substituted or unsubstituted C1-10 Alkyl, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 and selected from the group consisting of aryl, substituted or unsubstituted heteroaryl, -C(O)R5, -C(O)OR5, -C(O)NR6R7, -S(O)(O)R5 and -S(O)(O)NR6R7, where when alkyl is substituted, the substituent is selected from the group consisting of halo, C 1-6 Alkyloxy, cyano, nitro, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 selected from the group consisting of aryl, heteroaryl, -C(O)R5, -C(O)OR5, -C(O)NR6R7 and -NR6R7, where if heterocyclyl, aryl or heteroaryl is substituted, the substituent is each selected from the group consisting of: 1-6 Alkyl, C 1-6 Alkyloxy, halo, cyano, nitro, -C(O)R5, -C(O)OR5, -C(O)NR6R7, -NR6R7, and C substituted with 1, 2 or 3 halo. 1-6 Selected from the group consisting of alkyl; R5 is H or C 1-6 alkyl, and R and R are each independently H or C 1-6 alkyl, or R6 and R7 taken together are a heterocyclyl containing at least one nitrogen atom in the ring.

[0037] In the compound of the first specific example, R2 is absent, H, unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 selected from the group consisting of aryl and substituted or unsubstituted heteroaryl, where if the heterocyclyl, aryl or heteroaryl is substituted, the substituent is each selected from the group consisting of: 1-6 may be selected from the group consisting of alkyl, halo and -C(O)OR5, where R5 is H or C 1-6 may be alkyl; R3 is not present or C 1-10 Alkyl, C2-5 Heterocyclyl, C 6-10 may be selected from the group consisting of aryl and heteroaryl; R4 is H, substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 aryl, substituted or unsubstituted heteroaryl, where when alkyl is substituted, the substituents are selected from the group consisting of halo, C 1-6 Alkyloxy, cyano, nitro, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 aryl, heteroaryl, and -NR6R7, where if the heterocyclyl, aryl, or heteroaryl is substituted, the substituent is selected from the group consisting of: 1-6 Alkyl, C 1-6 Alkyloxy, halo, cyano, nitro, and C substituted with 1, 2 or 3 halo 1-6 It may be selected from the group consisting of alkyl.

[0038] In the present invention, a second specific example of the compound in which X1 and X4 in Chemical Formula 1 are carbon atoms (C) and X2 and X3 are nitrogen atoms (N) is: R2 is a substituted alkyl, each of which is a substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 aryl, or substituted or unsubstituted heteroaryl, where if the heterocyclyl, aryl, or heteroaryl is substituted, the substituent is, respectively, C 1-6 Alkyl, C 1-6 Selected from the group consisting of alkyloxy and halo; R3 is absent, H, halo, substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 2-10 Alkenyl, substituted or unsubstituted C 2-10 Alkynyl, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10and selected from the group consisting of aryl, substituted or unsubstituted heteroaryl, -C(O)R5, -C(O)OR5, -C(O)NR6R7, -S(O)(O)R5 and -S(O)(O)NR6R7, where when alkyl is substituted, the substituent is selected from the group consisting of halo, C 1-6 Alkyloxy, cyano, nitro, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 selected from the group consisting of aryl, heteroaryl, -C(O)R5, -C(O)OR5, -C(O)NR6R7 and -NR6R7, where if heterocyclyl, aryl or heteroaryl is substituted, the substituent is each selected from the group consisting of: 1-6 Alkyl, C 1-6 Alkyloxy, halo, cyano, nitro, -C(O)R5, -C(O)OR5, -C(O)NR6R7, -NR6R7, and C substituted with 1, 2 or 3 halo. 1-6 Selected from the group consisting of alkyl; R4 is H, halo, substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 and selected from the group consisting of aryl, substituted or unsubstituted heteroaryl, -C(O)R5, -C(O)OR5, -C(O)NR6R7, -S(O)(O)R5 and -S(O)(O)NR6R7, where when alkyl is substituted, the substituent is selected from the group consisting of halo, C 1-6 Alkyloxy, cyano, nitro, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 selected from the group consisting of aryl, heteroaryl, -C(O)R5, -C(O)OR5, -C(O)NR6R7 and -NR6R7, where if heterocyclyl, aryl or heteroaryl is substituted, the substituent is each selected from the group consisting of: 1-6 Alkyl, C 1-6 Alkyloxy, halo, cyano, nitro, -C(O)R5, -C(O)OR5, -C(O)NR6R7, -NR6R7, and C substituted with 1, 2 or 3 halo. 1-6 Selected from the group consisting of alkyl; R5 is H or C1-6 alkyl, and R and R are each independently H or C 1-6 alkyl, or R and R 7 are bonded to each other to form a heterocyclyl containing at least one nitrogen atom in the ring.

[0039] In the compound of the second embodiment, R and R may each be a substituted alkyl, and the substituents may each be a substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 aryl, or substituted or unsubstituted heteroaryl, where if the heterocyclyl, aryl, or heteroaryl is substituted, the substituent is, respectively, C 1-6 Alkyl, C 1-6 R4 may be selected from the group consisting of H or C 1-10 It can be alkyl.

[0040] In the present invention, a third specific example of the compound in which X1 and X4 in Chemical Formula 1 are carbon atoms (C) and X2 and X3 are nitrogen atoms (N) is: R2 is absent, H, halo, substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 2-10 Alkenyl, substituted or unsubstituted C 2-10 Alkynyl, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 and selected from the group consisting of aryl, substituted or unsubstituted heteroaryl, -C(O)R5, -C(O)OR5, -C(O)NR6R7, -S(O)(O)R5 and -S(O)(O)NR6R7, where when alkyl is substituted, the substituent is selected from the group consisting of halo, C 1-6 Alkyloxy, cyano, nitro, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 selected from the group consisting of aryl, heteroaryl, -C(O)R5, -C(O)OR5, -C(O)NR6R7 and -NR6R7, where if heterocyclyl, aryl or heteroaryl is substituted, the substituent is each selected from the group consisting of:1-6 Alkyl, C 1-6 Alkyloxy, halo, cyano, nitro, -C(O)R5, -C(O)OR5, -C(O)NR6R7, -NR6R7, and C substituted with 1, 2 or 3 halo. 1-6 Selected from the group consisting of alkyl; R3 is -S(O)(O)R5 or -S(O)(O)NR6R7; R4 is H, halo, substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 and selected from the group consisting of aryl, substituted or unsubstituted heteroaryl, -C(O)R5, -C(O)OR5, -C(O)NR6R7, -S(O)(O)R5 and -S(O)(O)NR6R7, where when alkyl is substituted, the substituent is selected from the group consisting of halo, C 1-6 Alkyloxy, cyano, nitro, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 selected from the group consisting of aryl, heteroaryl, -C(O)R5, -C(O)OR5, -C(O)NR6R7 and -NR6R7, where if heterocyclyl, aryl or heteroaryl is substituted, the substituent is each selected from the group consisting of: 1-6 Alkyl, C 1-6 Alkyloxy, halo, cyano, nitro, -C(O)R5, -C(O)OR5, -C(O)NR6R7, -NR6R7, and C substituted with 1, 2 or 3 halo. 1-6 Selected from the group consisting of alkyl; R5 is H, C 1-6 Alkyl, substituted or unsubstituted C 2-5 R6 and R7 are each independently selected from the group consisting of H, C 1-6or R6 and R7 may be bonded together to form a heterocyclyl having at least one nitrogen (N) atom in the ring and further containing or not containing one or more heteroatoms selected from N, O and S, wherein when the heterocyclyl, aryl or heteroaryl is substituted, the substituents are each selected from the group consisting of C 1-6 Alkyl, C 1-6 Alkyloxy, halo, nitro, cyano, -C(O)OR9, and C substituted with 1, 2 or 3 halo 1-6 alkyl, R9 is H or C 1-6 It is an alkyl.

[0041] In the compound of the third specific example, R2 is absent; R3 is -S(O)(O)R5; R4 is H, halo, substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 aryl, and substituted or unsubstituted heteroaryl; R5 is selected from the group consisting of H, C 1-6 Alkyl, substituted or unsubstituted C 2-5 may be selected from the group consisting of heterocyclyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; Wherein, when alkyl is substituted, the substituents are halo, C 1-6 Alkyloxy, cyano, nitro, substituted or unsubstituted C 2-5 Heterocyclyl, substituted or unsubstituted C 6-10 When the heterocyclyl, aryl or heteroaryl is substituted, the substituent is selected from the group consisting of: 1-6 Alkyl, C 1-6 Alkyloxy, halo, nitro, cyano, -C(O)OR9, and C substituted with 1, 2 or 3 halo 1-6 alkyl, R9 is H or C 1-6 It can be alkyl.

[0042] In the present invention, the halo may be one or more selected from fluoro, chloro, bromo and iodo. The aryl is preferably phenyl or naphthyl, and the heteroaryl is preferably a 5- to 10-membered heteroaromatic ring group having one or more heteroatoms selected from N, O and S in the ring, examples of which include, but are not limited to, pyridinyl, pyridazinyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, furanyl, etc. The heterocyclyl is a 3- to 7-membered heteroaliphatic ring group having one or more heteroatoms selected from N, O and S in the ring, examples of which include, but are not limited to, aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, etc.

[0043] The compounds of Formula 1 of the present invention may include the following compounds 1 to 70: Compound 1: 1-phenylimidazo[1,2-a]quinoline-4,5-dione; Compound 2: 1-(4-fluorophenyl)imidazo[1,2-a]quinoline-4,5-dione; Compound 3: 1-isopropylimidazo[1,2-a]quinoline-4,5-dione; Compound 4: 1-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]quinoline-4,5-dione; Compound 5: Ethyl 4,5-dioxo-4,5-dihydroimidazo[1,2-a]quinoline-2-carboxylate; Compound 6: Ethyl 4,5-dioxo-1-phenyl-4,5-dihydroimidazo[1,2-a]quinoline-2-carboxylate; Compound 7: N,N-dimethyl-4,5-dioxo-1-phenyl-4,5-dihydroimidazo[1,2-a]quinoline-2-carboxamide; Compound 8: N-methyl-4,5-dioxo-1-phenyl-4,5-dihydroimidazo[1,2-a]quinoline-2-carboxamide; Compound 9: 3-methyl-1-phenyl-1H-benzo[g]indazole-4,5-dione; Compound 10: 3-isopropyl-1-phenyl-1H-benzo[g]indazole-4,5-dione; Compound 11: 3-heptyl-1-phenyl-1H-benzo[g]indazole-4,5-dione; Compound 12: 3-phenethyl-1-phenyl-1H-benzo[g]indazole-4,5-dione; Compound 13: 1,3-diphenyl-1H-benzo[g]indazole-4,5-dione; Compound 14: 3-(4-fluorophenyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione; Compound 15: 3-(3,4-difluorophenyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione; Compound 16: 3-(bromomethyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione; Compound 17: 3-((dimethylamino)methyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione; Compound 18: 3-(methoxymethyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione; Compound 19: 3-(isopropoxymethyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione; Compound 20: 1-isopropyl-3-methyl-1H-benzo[g]indazole-4,5-dione; Compound 21: 2-isopropyl-3-methyl-2H-benzo[g]indazole-4,5-dione; Compound 22: 1,3-dimethyl-1H-benzo[g]indazole-4,5-dione; Compound 23: 2,3-dimethyl-2H-benzo[g]indazole-4,5-dione; Compound 24: 3-((1H-imidazol-1-yl)methyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione; Compound 25: 1-(4-fluorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione; Compound 26: 1-(4-chlorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione; Compound 27: 1-(3,5-difluorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione; Compound 28: 1-(2,4-dichlorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione; Compound 29: 3-Methyl-1-p-tolyl-1H-benzo[g]indazole-4,5-dione; Compound 30: 3-methyl-1-(pyridin-2-yl)-1H-benzo[g]indazole-4,5-dione; Compound 31: 3-methyl-1-(pyridin-3-yl)-1H-benzo[g]indazole-4,5-dione; Compound 32: 1-(2,4-difluorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione; Compound 33: 1-phenyl-1H-benzo[g]indazole-4,5-dione; Compound 34: 1-phenyl-3-(trifluoromethyl)-1H-benzo[g]indazole-4,5-dione; Compound 35: 7-fluoro-3-methyl-1-phenyl-1H-benzo[g]indazole-4,5-dione; Compound 36: 1-(3,5-dichlorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione; Compound 37: 4-(3-methyl-4,5-dioxo-4,5-dihydro-1H-benzo[g]indazol-1-yl)benzoic acid; Compound 38: 3-methyl-1-(naphthalen-1-yl)-1H-benzo[g]indazole-4,5-dione; Compound 39: 1-(5-chloropyridin-3-yl)-3-methyl-1H-benzo[g]indazole-4,5-dione; Compound 40: 3-methyl-1-(thiazol-2-yl)-1H-benzo[g]indazole-4,5-dione; Compound 41: 3-methyl-1-(pyridin-4-yl)-1H-benzo[g]indazole-4,5-dione; Compound 42: 3-methyl-2-(pyridin-4-yl)-2H-benzo[g]indazole-4,5-dione; Compound 43: 3-Methyl-1H-benzo[g]indazole-4,5-dione; Compound 44: 3-Methyl-2-(phenylsulfonyl)-2H-benzo[g]indazole-4,5-dione; Compound 45: 3-methyl-2-(4-fluorophenylsulfonyl)-2H-benzo[g]indazole-4,5-dione; Compound 46: 2-(2-chlorophenylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione; Compound 47: 2-(3-chlorophenylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione; Compound 48: 3-Methyl-2-(pyridin-3-ylsulfonyl)-2H-benzo[g]indazole-4,5-dione; Compound 49: 2-(4-chlorophenylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione; Compound 50: 3-Methyl-2-tosyl-2H-benzo[g]indazole-4,5-dione; Compound 51: 2-(4-methoxyphenylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione; Compound 52: methyl 4-(3-methyl-4,5-dioxo-4,5-dihydro-2H-benzo[g]indazol-2-ylsulfonyl)benzoate; Compound 53: 2-(cyclopropylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione; Compound 54: 2-(cyclopentylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione; Compound 55: 4-(3-methyl-4,5-dioxo-4,5-dihydro-2H-benzo[g]indazol-2-ylsulfonyl)benzonitrile; Compound 56: 3-Methyl-2-(4-nitrophenylsulfonyl)-2H-benzo[g]indazole-4,5-dione; Compound 57: 3-Methyl-2-(4-(trifluoromethyl)phenylsulfonyl)-2H-benzo[g]indazole-4,5-dione; Compound 58: 2-(3,4-difluorophenylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione; Compound 59: 2-(2,4-difluorophenylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione; Compound 60: 3-Methyl-2-(quinolin-8-ylsulfonyl)-2H-benzo[g]indazole-4,5-dione; Compound 61: 3-methyl-2-(1-methyl-1H-imidazol-2-ylsulfonyl)-2H-benzo[g]indazole-4,5-dione; Compound 62: 3-Methyl-2-(morpholinosulfonyl)-2H-benzo[g]indazole-4,5-dione; Compound 63: 1-benzyl-3-methyl-1H-benzo[g]indazole-4,5-dione; Compound 64: 3-Methyl-1-phenethyl-1H-benzo[g]indazole-4,5-dione; Compound 65: 1-(4-fluorophenethyl)-3-methyl-1H-benzo[g]indazole-4,5-dione; Compound 66: 2-(4-fluorophenethyl)-3-methyl-2H-benzo[g]indazole-4,5-dione; Compound 67: 3-Methyl-1-(3-phenylpropyl)-1H-benzo[g]indazole-4,5-dione; Compound 68: 3-Methyl-1-(4-methylphenethyl)-1H-benzo[g]indazole-4,5-dione; Compound 69: 3-methyl-2-(4-methylphenethyl)-2H-benzo[g]indazole-4,5-dione; and Compound 70: 2-(2-fluorophenethyl)-3-methyl-2H-benzo[g]indazole-4,5-dione.

[0044] A second aspect of the present invention relates to a compound represented by Chemical Formula 2, which is a preparation intermediate of the compound of Chemical Formula 1, or a salt, enantiomer, partial stereoisomer or tautomer thereof:

[0045] [ka]

[0046] In the formula, R1, R2, R3, R4, X2, X3, X4, [ka] and [ka] is as defined for formula 1, and R8 is a protecting group for a conventional hydroxy group known in the art. Examples of such protecting groups include 1-6 Alkyl;C 6-10 Aryl-substituted C 1-6 Alkyl, for example, benzyl, trityl, methoxybenzyl, etc.; C 1-6 Alkoxy-substituted C 1-6 Alkyl, for example, methoxymethyl, methoxyethoxymethyl, etc.; carbonyl, for example, acetyl, pivaloyl, etc.; heterocyclyl, for example, tetrahydropyranyl, tetrahydrofuranyl, etc.; C 1-6 Alkyl-substituted silyl, for example, trimethylsilyl, triisopropylsilyl, t-butyldimethylsilyl, etc.; C 1-6 Alkylcarbonyl, for example, acetyl, pivaloyl, and the like, are included, but are not limited to these.

[0047] The compound of Formula 2 is 5-(benzyloxy)-1-phenylimidazo[1,2-a]quinoline; Ethyl 5-(benzyloxy)imidazo[1,2-a]quinoline-2-carboxylate; 5-(benzyloxy)-1-(4-fluorophenyl)imidazo[1,2-a]quinoline; 5-(benzyloxy)-1-isopropylimidazo[1,2-a]quinoline; 5-(benzyloxy)-1-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]quinoline; 5-Methoxy-3-methyl-1-phenyl-1H-benzo[g]indazole; (5-Methoxy-1-phenyl-1H-benzo[g]indazol-3-yl)methanol; 3-(Bromomethyl)-5-(methoxymethoxy)-1-phenyl-1H-benzo[g]indazole; 5-Methoxy-3-methyl-1H-benzo[g]indazole; 1-(4-fluorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole; 1-(4-chlorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole; 1-(3,5-difluorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole; 1-(2,4-dichlorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole; 5-Methoxy-3-methyl-1-p-tolyl-1H-benzo[g]indazole; 5-Methoxy-3-methyl-1-(pyridin-2-yl)-1H-benzo[g]indazole; 5-Methoxy-3-methyl-1-(pyridin-3-yl)-1H-benzo[g]indazole; 1-(2,4-difluorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole; 5-Methoxy-1-phenyl-1H-benzo[g]indazole; 5-Methoxy-1-phenyl-3-(trifluoromethyl)-1H-benzo[g]indazole; 7-Fluoro-5-methoxy-3-methyl-1-phenyl-1H-benzo[g]indazole; 1-(3,5-dichlorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole; Methyl 4-(5-methoxy-3-methyl-1H-benzo[g]indazol-1-yl)benzoate; 5-Methoxy-3-methyl-1-(naphthalen-1-yl)-1H-benzo[g]indazole; and It may be selected from the group consisting of 1-(5-chloropyridin-3-yl)-5-methoxy-3-methyl-1H-benzo[g]indazole.

[0048] A third aspect of the present invention relates to a pharmaceutical composition comprising a compound represented by the above chemical formula 1 as an active ingredient, or a chemically acceptable salt, hydrate, solvate, enantiomer, partial stereoisomer, tautomer or prodrug thereof.

[0049] The pharmaceutical composition may further comprise one or more selected from the group consisting of carriers, excipients and diluents commonly known in the field of pharmaceutical compositions.

[0050] Since the compound of formula 1 according to the present invention can be used as a substrate for NQO1 and inhibit the expression and activity of inflammatory cytokines, the pharmaceutical composition can be used for the prevention or treatment of diseases associated with NQO1 activity.

[0051] Working Example The present invention will be described in more detail below with reference to examples. These examples are only intended to describe the present invention in more detail, and the scope of the present invention is not limited by these examples.

[0052] Production Example 1: Synthesis of Intermediate 1 (4-(benzyloxy)quinolin-2-amine) 2-Amino-4-hydroxyquinoline hydrate (5mmol) and sodium hydride (10mmol) were dissolved in dimethylformamide (20mL) at 0℃. After stirring for 5 minutes, the temperature was raised to room temperature, and benzyl bromide (5.5mmol) was added and reacted for 17 hours. A 1:1 mixture of ethyl acetate and n-hexane was gradually added to the reaction solution and stirred. The solid formed was filtered, and the filtrate was washed with a saturated aqueous solution of sodium bicarbonate and dried to obtain the title compound without further purification. Yield: 44%, white solid. 1 H NMR (300MHz, DMSO-d6) δ:7.85-7.82(d, J=8.0Hz, 1H), 7.53-7.51(m, 2H), 7.46-7.33(m, 5H), 7.11-7.06(m, 1H), 6.30(br s, 2H), 6.28(s, 1H), 5.23(s, 2H).

[0053] Preparation Example 2: Synthesis of Intermediate 2 (Ethyl 5-(benzyloxy)imidazo[1,2-a]quinoline-2-carboxylate) (1) Synthesis of 1-(4-(benzyloxy)-2-iminoquinolin-1(2H)-yl)pentane-2,3-dione bromate 4-(benzyloxy)quinolin-2-amine (1 mmol, intermediate 1) was dissolved in THF (10 mL) at room temperature, and 3-bromo-2-oxopropanoate (2 mmol) was added and reacted for 12 hours. After the reaction was completed, the solid formed was filtered while washing with THF. The title compound was obtained in a solid state without further purification. (2) Synthesis of intermediate 2 (ethyl 5-(benzyloxy)imidazo[1,2-a]quinoline-2-carboxylate) Dissolve the 1-(4-(benzyloxy)-2-iminoquinolin-1(2H)-yl)pentane-2,3-dione bromate (1 mmol) prepared above in ethanol (10 mL) and react under heating and reflux for 10 hours. After the reaction is completed, concentrate the solvent under reduced pressure and purify by column chromatography. Yield: 57%, pale yellow solid. 1H NMR (300MHz, DMSO-d6)δ:8.54(s, 1H), 8.29-8.26(m, 1H), 7.89(d, J=8.3Hz, 1H), 7.73-7.67(m, 1H), 7.55-7.39(m, 6H), 6.88(s, 1H), 5.27(s, 2H), 4.46(q, J=7.2Hz, 2H), 1.45(t, J=7.2Hz, 3H).

[0054] Production Example 3: Synthesis of Intermediate 3 (1-bromo-4-methoxy-2-naphthoic acid) (1) Synthesis of methyl 1-hydroxy-3-naphthoate Benzaldehyde (282mmol) and dimethylsuccinate (310.2mmol) are dissolved in methanol (100mL), 25% sodium methoxide methanol solution (366.6mmol) is slowly added, and the temperature is raised to react under reflux for 12 hours. When the reaction is complete, 3M HCl is added to acidify the reaction solution to pH 1, and the solution is extracted with methylene chloride, the organic layer is dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting mixture is concentrated under reduced pressure without any additional purification, redissolved in THF (80mL), and trifluoroacetic anhydride (282mmol) is added while stirring at room temperature, and the temperature is raised to react under reflux. When the reaction is complete, the reaction solution is cooled to room temperature and neutralized with saturated aqueous sodium carbonate at 0°C. The reaction mixture is extracted with ethyl acetate, the organic layer is dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained compound is purified by column chromatography. Yield: 30%, pale yellow solid. 1 H NMR (300MHz, CDCl3) δ: 8.26-8.21 (m, 2H), 7.93-7.90 (m, 1H), 7.63-7.51 (m, 3H), 5.95 (s, 1H), 3.98 (s, 3H). (2) Synthesis of methyl 4-methoxy-2-naphthoate Methyl 1-hydroxy-3-naphthoate (4.54mmol) and potassium carbonate (9.08mmol) were dissolved in dimethylformamide (15mL), iodomethane (9.54mmol) was added, and the mixture was stirred at room temperature for 2 hours. When the reaction was completed, water was added to terminate the reaction, and the mixture was extracted with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained compound was used in the next reaction without further purification. (3) Synthesis of methyl 1-bromo-4-methoxy-2-naphthoate Dissolve methyl 1-hydroxy-3-naphthoate (24.7 mmol) in acetonitrile (60 mL). Add N-bromosuccinimide (26 mmol) to the reaction solution, raise the temperature and react under reflux. When the reaction is complete, concentrate the reaction solution under reduced pressure, and purify the resulting solid by column chromatography. Yield: 90%, pale yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.42(d, J=8.3Hz, 1H), 8.30(d, J=7.7Hz, 1H), 7.70-7.59(m, 2H), 7.05(s, 1H), 4.05(s, 3H), 4.03(s, 3H). (4) Synthesis of intermediate 3 (1-bromo-4-methoxy-2-naphthoic acid) Dissolve methyl 1-bromo-4-methoxy-2-naphthoate (17.8 mmol) in a mixture of THF, methanol and water (1:1:1 v / v), add potassium hydroxide (53.4 mmol), and stir under reflux for 3 hours. After cooling the reaction mixture to room temperature, add 1M aqueous hydrochloric acid to acidify it, extract with ethyl acetate, dry the organic layer over anhydrous magnesium sulfate and concentrate under reduced pressure. Recrystallize from methylene chloride to obtain the title compound. Yield: 99%, white solid. 1 H NMR (300MHz, CDCl3) δ: 8.48 (d, J=7.9Hz, 1H), 8.31 (d, J=8.0Hz, 1H), 7.72-7.60 (m, 2H), 7.25 (s, 1H), 4.06 (s, 3H).

[0055] Production Example 4: Synthesis of Intermediate 4 (1-(1-bromo-4-methoxynaphthalen-2-yl)ethan-1-one) (1) Synthesis of 1-bromo-N,4-dimethoxy-N-methyl-2-naphthamide 1-Bromo-4-methoxy-2-naphthoic acid (10 mmol, intermediate 3) was suspended in 100 mL of methylene chloride, and N,O-dimethylhydroxyamine hydrochloride (11 mmol) was added. Triethylamine (40 mmol) was added to the reaction solution, and the mixture was stirred at room temperature for 5 minutes. Bis(2-oxo-3-oxazolidinyl)phosphinic chloride (11 mmol) was added and the mixture was stirred at room temperature for 12 hours. When the reaction was completed, 100 mL of 1M aqueous hydrochloric acid was added, and the mixture was stirred for 10 minutes and extracted with methylene chloride. The extract was washed with saturated aqueous sodium bicarbonate and distilled water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The product was used in the next reaction without further purification. (2) Synthesis of intermediate 4 (1-(1-bromo-4-methoxynaphthalen-2-yl)ethan-1-one) Dissolve 1-bromo-N,4-dimethoxy-N-methyl-2-naphthamide (10 mmol) in 100 mL of THF, cool the reaction solution to 0°C, slowly add methylmagnesium bromide (30 mmol) to the reaction solution, and stir for 10 minutes. Allow the reaction solution to warm to room temperature and stir for 5 hours. When the reaction is complete, cool the reaction solution to 0°C, slowly add 100 mL of 1M NH4Cl aqueous solution, stir for 10 minutes, and then separate the organic layer. Extract the aqueous layer with ethyl acetate, wash the organic layer with salt water, dry with anhydrous magnesium sulfate, concentrate under reduced pressure, and purify by column chromatography. Yield: 80%, white solid. 1 H NMR (300MHz, CDCl3) δ: 8.33-8.27 (m, 2H), 7.70-7.59 (m, 2H), 6.73 (s, 1H), 4.02 (s, 3H), 2.74 (s, 3H).

[0056] Preparation Example 5: Synthesis of Intermediate 5 (5-methoxy-3-methyl-1-phenyl-1H-benzo[g]indazole) (1) Synthesis of 1-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)-2-phenylhydrazine 1-(1-Bromo-4-methoxynaphthalen-2-yl)ethan-1-one (7.2 mmol, intermediate 4), phenylhydrazine (10.8 mmol) and p-toluenesulfonic acid monohydrate (1.4 mmol) were dissolved in ethanol (45 mL). The temperature was raised and the reaction was allowed to proceed under reflux for 3 hours. When the reaction was complete, the reaction solution was cooled to 0°C and stirred for 3 hours. The resulting solid was filtered, washed with cold ethanol and then dried under vacuum to obtain a white solid, which was used in the next reaction without further purification. (2) Synthesis of intermediate 5 (5-methoxy-3-methyl-1-phenyl-1H-benzo[g]indazole) 1-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)-2-phenylhydrazine (5 mmol) is dissolved in 1,4-dioxane (12.5 mL). Copper iodide (5 mol%), trans-4-hydroxy-L-proline (5 mol%) and potassium hydroxide (10 mmol) are added to the reaction solution, and the mixture is allowed to react under reflux for 10 hours. After the reaction solution is cooled to room temperature, water is added and the mixture is extracted with ethyl acetate. The organic layer is dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and then purified by column chromatography. Yield: 35%, light brown solid. 1 H NMR (300MHz, DMSO-d6) δ: 8.30 (m, 1H), 7.67-7.39 (m, 8H), 7.18 (s, 1H), 4.05 (s, 3H), 2.58 (s, 3H).

[0057] Production Example 6: Synthesis of Intermediate 6 ((5-methoxy-1-phenyl-1H-benzo[g]indazol-3-yl)methanol) (1) Synthesis of 1-(1-bromo-4-methoxynaphthalen-2-yl)-2-hydroxyethan-1-one 1-(1-Bromo-4-methoxynaphthalen-2-yl)ethan-1-one (62.44 mmol, intermediate 4), KOH (343.42 mmol) and PhI(OAc)2 (78.05 mmol) are dissolved in methanol (400 mL). After reacting for 5 hours, the methanol is removed under reduced pressure, water is added to the reaction solution, and then it is extracted with ethyl acetate. The organic layer is dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue is dissolved in methanol, and 2N HCl is added and stirred overnight. When the reaction is complete, the methanol is removed, the aqueous layer is extracted with ethyl acetate, and the organic layer is washed with saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and then purified by column chromatography. Yield: 60%, white solid. 1 H NMR (300MHz, CDCl3)δ:8.35-8.29(m, 2H), 7.72-7.60(m, 2H), 6.79(s, 1H), 4.89(d, J=4.7Hz, 2H), 4.03(s, 3H), 3.36(br s, 1H). (2) Synthesis of 2-(1-bromo-4-methoxynaphthalen-2-yl)-2-(2-phenylhydrazono)ethan-1-ol The title compound was synthesized by the procedure described in Preparation 5(1) using the above prepared 1-(1-bromo-4-methoxynaphthalen-2-yl)-2-hydroxyethan-1-one (37.46 mmol) as the starting material. (3) Synthesis of intermediate 6 (5-methoxy-1-phenyl-1H-benzo[g]indazol-3-yl)methanol The title compound was synthesized by the procedure described in Preparation 5(2) using the above-prepared 2-(1-bromo-4-methoxynaphthalen-2-yl)-2-(2-phenylhydrazono)ethan-1-ol (25.98 mmol) as the starting material. Yield: 56%, light brown solid. 1H NMR (300MHz, CDCl3)δ:8.27(d, J=8.2Hz, 1H), 7.44-7.39(m, 7H), 7.22(t, J=7.5Hz, 1H), 6.96(s, 1H), 5.00(s, 2H), 3.96(s, 3H).

[0058] Preparation Example 7: Synthesis of Intermediate 7 (3-(bromomethyl)-5-(methoxymethoxy)-1-phenyl-1H-benzo[g]indazole) (1) Synthesis of 3-(bromomethyl)-5-methoxy-1-phenyl-1H-benzo[g]indazole Dissolve 5-methoxy-1-phenyl-1H-benzo[g]indazol-3-yl)methanol (14.5 mmol, intermediate 6) in methylene chloride (100 mL). Add PBr3 with stirring at room temperature and react for 5 hours. When the reaction is complete, add water to terminate the reaction, and extract the reaction solution with methylene chloride. The extract is washed with salt water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography. Yield: 67%, brown solid. 1 H NMR (300MHz, CDCl3)δ:8.40(d, J=8.8Hz, 1H), 7.64-7.56(m, 5H), 7.55-7.51(m, 2H), 7.35(t, J=8.2Hz, 1H), 7.05(s, 1H), 4.95(s, 2H), 4.12(s, 3H). (2) Synthesis of 3-(bromomethyl)-1-phenyl-1H-benzo[g]indazol-5-ol Dissolve 3-(bromomethyl)-5-methoxy-1-phenyl-1H-benzo[g]indazole (5 mmol) in methylene chloride (30 mL). Then, lower the temperature to 0°C, slowly add BBr3 (15 mmol), and warm the temperature to room temperature and react for 1 hour. Add H2O to the reaction solution, then extract with ethyl acetate. Recrystallize from methylene chloride and n-hexane to obtain a brown solid, which was used in the next reaction without further purification. (3) Synthesis of Intermediate 7 3-(bromomethyl)-5-(methoxymethoxy)-1-phenyl-1H-benzo[g]indazole Dissolve 3-(bromomethyl)-1-phenyl-1H-benzo[g]indazol-5-ol (7.60 mmol) in DMF (30 mL). Lower the temperature to 0°C, add chloromethyl methyl ether (19.0 mmol) and N,N-diisomethylpropylethylamine (19.0 mmol), and gradually warm to room temperature to react. After the reaction is complete, add water to terminate the reaction, and extract the mixture with ethyl acetate. Wash the extract with salt water, dry over anhydrous magnesium sulfate, concentrate under reduced pressure, and purify by column chromatography. Yield: 32%, white solid. 1 H NMR (300MHz, CDCl3)δ:8.40(d, J=7.6Hz, 1H), 7.62-7.54(m, 7H), 7.38-7.35(m, 2H), 5.48(s, 2H), 5.05(s, 2H), 3.61(s, 3H).

[0059] Preparation Example 8: Synthesis of Intermediate 8 (5-methoxy-3-methyl-1H-benzo[g]indazole) (1) Synthesis of (1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)hydrazine The title compound was synthesized by the procedure described in Preparation 5(1) using 1-(1-bromo-4-methoxynaphthalen-2-yl)ethan-1-one (11.0 mmol, Intermediate 4) and hydrazine monohydrate (12.1 mmol) as starting materials and reactants, and then used in the next reaction without further purification. (2) Synthesis of intermediate 8 (5-methoxy-3-methyl-1H-benzo[g]indazole) The title compound was synthesized by the procedure described in Preparation 5(2) using (1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)hydrazine as the starting material. Yield: 31%, light brown solid. 1H NMR (300MHz, CDCl3)δ: 13.2(s, 1H), 8.34(d, J=7.7Hz, 1H), 8.20(d, J=7.7Hz, 1H), 7.66-7.53(m, 2H), 7.03(s, 1H), 3.97(s, 3H), 2.57(s, 3H).

[0060] Preparation Example 9: Synthesis of Intermediate 9 (1-(4-fluorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole) (1) Synthesis of 1-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)-2-(4-fluorophenyl)hydrazine The title compound was synthesized by the procedure described in Preparation 5(1) using 1-(1-bromo-4-methoxynaphthalen-2-yl)ethan-1-one (7.2 mmol, Intermediate 4) and 4-fluorophenylhydrazine (10.8 mmol) as starting materials and reactants, and then used in the next reaction without further purification. (2) Synthesis of intermediate 9 (1-(4-fluorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole) The title compound was synthesized by the procedure described in Preparation 5(2) using 1-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)-2-(4-fluorophenyl)hydrazine (5 mmol) as the starting material. Yield: 32%, light brown solid. 1 H NMR (300MHz, DMSO-d6) δ: 8.41-8.38(m, 1H), 7.57-7.52(m, 4H), 7.36-7.33(m, 1H), 7.28-7.25(m, 2H), 6.92-6.90(m, 1H), 4.10(s, 3H), 2.66(s, 3H).

[0061] Preparation Example 10: Synthesis of Intermediate 10 (1-(4-chlorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole) (1) Synthesis of 1-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)-2-(4-chlorophenyl)hydrazine The title compound was synthesized by the procedure described in Preparation 5(1) using 1-(1-bromo-4-methoxynaphthalen-2-yl)ethan-1-one (7.2 mmol, Intermediate 4) and 4-chlorophenylhydrazine as starting materials and reactants, and then used in the next reaction without further purification. (2) Synthesis of intermediate 10 (1-(4-chlorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole) The title compound was synthesized by the procedure described in Preparation 5(2) using 1-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)-2-(4-chlorophenyl)hydrazine (5 mmol) as the starting material. Yield: 36%, light brown solid. 1 H NMR (300MHz, DMSO-d6) δ: 8.37-8.31(m, 1H), 7.61-7.58(m, 1H), 7.55-7.50(m, 5H), 7.37-7.30(m, 1H), 6.89(s, 1H), 4.08(s, 3H), 2.64(s, 3H).

[0062] Preparation Example 11: Synthesis of Intermediate 11 (1-(3,5-difluorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole) (1) Synthesis of 1-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)-2-(3,5-difluorophenyl)hydrazine The title compound was synthesized by the procedure described in Preparation 5(1) using 1-(1-bromo-4-methoxynaphthalen-2-yl)ethan-1-one (7.2 mmol, Intermediate 4) and 3,5-difluorophenylhydrazine (10.8 mmol) as starting materials and reactants, and then used in the next reaction without further purification. (2) Synthesis of intermediate 11 (1-(3,5-difluorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole) The title compound was synthesized according to the procedure described in Preparation 5(2) using 1-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)-2-(3,5-difluorophenyl)hydrazine (5 mmol) as the starting material. Yield: 41%, light brown solid. 1 H NMR (300MHz, DMSO-d6)δ:8.40-8.37(m, 1H), 7.75-7.71(m, 1H), 7.57-7.51(m, 1H), 7.44-7 .39(m, 1H), 7.17-7.12(m, 2H), 6.96-6.91(m, 1H), 6.89(s, 1H), 4.09(s, 3H), 2.64(s, 3H).

[0063] Preparation Example 12: Synthesis of Intermediate 12 (1-(2,4-dichlorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole) (1) Synthesis of 1-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)-2-(2,4-dichlorophenyl)hydrazine The title compound was synthesized by the procedure described in Preparation 5(1) using 1-(1-bromo-4-methoxynaphthalen-2-yl)ethan-1-one (7.2 mmol, Intermediate 4) and 2,4-dichlorophenylhydrazine (10.8 mmol) as starting materials and reactants, and then used in the next reaction without further purification. (2) Synthesis of intermediate 12 (1-(2,4-dichlorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole) The title compound was synthesized by the procedure described in Preparation 5(2) using 1-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)-2-(2,4-dichlorophenyl)hydrazine (5 mmol) as the starting material. Yield: 53%, light brown solid. 1H NMR (300MHz, DMSO-d6) δ:8.37-8.34(m, 1H), 7.65(s, 1H), 7.55-7.46(m, 3H), 7.35-7.30(m, 1H), 7.24-7.19(m, 1H), 6.91(s, 1H), 4.08(s, 3H), 2.66(s, 3H).

[0064] Preparation Example 13: Synthesis of Intermediate 13 (5-methoxy-3-methyl-1-p-tolyl-1H-benzo[g]indazole) (1) Synthesis of 1-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)-2-p-tolylhydrazine The title compound was synthesized by the procedure described in Preparation 5(1) using 1-(1-bromo-4-methoxynaphthalen-2-yl)ethan-1-one (7.2 mmol, Intermediate 4) and p-tolylhydrazine (10.8 mmol) as starting materials and reactants, and then used in the next reaction without further purification. (2) Synthesis of intermediate 13 (5-methoxy-3-methyl-1-p-tolyl-1H-benzo[g]indazole) The title compound was synthesized by the procedure described in Preparation 5(2) using 1-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)-2-p-tolylhydrazine (5 mmol) as the starting material. Yield: 26%, light brown solid. 1 H NMR (300MHz, DMSO-d6)δ:8.36-8.30(m, 1H), 7.61-7.56(m, 1H), 7.53-7.43(m , 3H), 7.36-7.33(m, 3H), 6.90(s, 1H), 4.08(s, 3H), 2.64(s, 3H), 2.49(s, 3H).

[0065] Preparation Example 14: Synthesis of Intermediate 14 (5-methoxy-3-methyl-1-(pyridin-2-yl)-1H-benzo[g]indazole) (1) Synthesis of 2-(2-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)hydrazyl)pyridine The title compound was synthesized by the procedure described in Preparation 5(1) using 1-(1-bromo-4-methoxynaphthalen-2-yl)ethan-1-one (7.2 mmol, Intermediate 4) and 2-hydrazinopyridine (10.8 mmol) as starting materials and reactants, and then used in the next reaction without further purification. (2) Synthesis of intermediate 14 (5-methoxy-3-methyl-1-(pyridin-2-yl)-1H-benzo[g]indazole) The title compound was synthesized by the procedure described in Preparation 5(2) using 2-(2-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)hydrazyl)pyridine (5 mmol) as the starting material. Yield: 30%, light brown solid. 1 H NMR (300MHz, DMSO-d6) δ:8.65-8.62(m, 1H), 8.39-8.36(m, 1H), 8.05-7.89(m, 2H), 7.83-7.7 1(m, 1H), 7.61-7.49(m, 1H), 7.47-7.33(m, 2H), 6.90-6.87(m, 1H), 4.08(s, 3H), 2.65(s, 3H).

[0066] Preparation Example 15: Synthesis of Intermediate 15 (5-methoxy-3-methyl-1-(pyridin-3-yl)-1H-benzo[g]indazole) (1) Synthesis of 3-(2-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)hydrazyl)pyridine The title compound was synthesized by the procedure described in Preparation 5(1) using 1-(1-bromo-4-methoxynaphthalen-2-yl)ethan-1-one (7.2 mmol, Intermediate 4) and 3-hydrazinopyridine (10.8 mmol) as starting materials and reactants, and then used in the next reaction without further purification. (2) Synthesis of intermediate 15 (5-methoxy-3-methyl-1-(pyridin-3-yl)-1H-benzo[g]indazole) The title compound was synthesized by the procedure described in Preparation 5(2) using 3-(2-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)hydrazyl)pyridine (5 mmol) as the starting material. Yield: 22%, light brown solid. 1 H NMR (300MHz, DMSO-d6) δ:8.93-8.85(m, 1H), 8.80-8.71(m, 1H), 8.44-8.36(m, 1H), 7.97-7.8 9(m, 1H), 7.61-7.48(m, 3H), 7.41-7.32(m, 1H), 6.92-6.87(m, 1H), 4.09(s, 3H), 2.67(s, 3H).

[0067] Preparation Example 16: Synthesis of Intermediate 16 (1-(2,4-difluorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole) (1) Synthesis of 1-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)-2-(2,4-difluorophenyl)hydrazine The title compound was synthesized by the procedure described in Preparation 5(1) using 1-(1-bromo-4-methoxynaphthalen-2-yl)ethan-1-one (7.2 mmol, Intermediate 4) and 2,4-difluorophenylhydrazine (10.8 mmol) as starting materials and reactants, and then used in the next reaction without further purification. (2) Synthesis of intermediate 16 (1-(2,4-difluorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole) The title compound was synthesized by the procedure described in Preparation 5(2) using 1-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)-2-(2,4-difluorophenyl)hydrazine (5 mmol) as the starting material. Yield: 37%, light brown solid. 1H NMR (300MHz, DMSO-d6) δ:8.42-8.39(m, 1H), 7.69(s, 1H), 7.56-7.47(m, 3H), 7.39-7.33(m, 1H), 7.30-7.26(m, 1H), 6.96(s, 1H), 4.09(s, 3H), 2.68(s, 3H).

[0068] Preparation Example 17: Synthesis of Intermediate 17 (5-methoxy-1-phenyl-1H-benzo[g]indazole) (1) Synthesis of 1-bromo-4-methoxy-2-naphthaldehyde 1-Bromo-N,4-dimethoxy-N-methyl-2-naphthamide (35.6 mmol, product of step (1) of Preparation 4) is dissolved in 200 mL of THF, and the temperature of the reaction solution is cooled to 0°C. Then, diisobutylaluminum hydride solution (71.3 mmol) is slowly added to the reaction solution, and the mixture is stirred for 10 minutes. The temperature of the reaction solution is raised to room temperature, and the mixture is stirred for 10 hours. When the reaction is completed, the reaction solution is cooled to 0°C, and 100 mL of 1M NH4Cl aqueous solution is slowly added, and the mixture is stirred for 10 minutes, and the organic layer is separated. The aqueous layer is extracted with ethyl acetate, and the organic layer is collected and washed with brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography. Yield: 42%, white solid. 1 H NMR (300MHz, CDCl3)δ: 10.66(s, 1H), 8.50-8.47(m, 1H), 8.33-8.31(m, 1H), 7.71-7.68(m, 2H), 7.30(s, 1H), 4.07(s, 3H). (2) Synthesis of 1-((1-bromo-4-methoxynaphthalen-2-yl)methylene)-2-phenylhydrazine The title compound was synthesized by the procedure described in Preparation 5(1) using 1-bromo-4-methoxy-2-naphthaldehyde (7.5 mmol) as the starting material and then used in the next reaction without further purification. (3) Synthesis of intermediate 17 (5-methoxy-1-phenyl-1H-benzo[g]indazole) The title compound was synthesized by the procedure described in Preparation 5(2) using 1-((1-bromo-4-methoxynaphthalen-2-yl)methylene)-2-phenylhydrazine (5 mmol) as the starting material. Yield: 27%, brown solid. 1 H NMR (300MHz, CDCl3)δ: 8.34-8.36(m, 1H), 8.14(s, 1H), 7.58-7.49(m, 7H), 7.35-7.30(m, 1H), 7.00(s, 1H), 4.06(s, 3H).

[0069] Preparation Example 18: Synthesis of Intermediate 18 (5-methoxy-1-phenyl-3-(trifluoromethyl)-1H-benzo[g]indazole) (1) Synthesis of 1-(1-bromo-4-methoxynaphthalen-2-yl)-2,2,2-trifluoroethanol Dissolve 1-bromo-4-methoxy-2-naphthaldehyde (6.04 mmol) in THF (7.5 mL). Lower the temperature to 0°C, add TMS-CF3 (15.08 mmol) and TBAF solution (1M THF solution, 0.6 mmol), and react for 8 hours. Add 1 mL of H2O, stir for 10 hours, add more water, and extract with ethyl acetate. Dry the organic layer over anhydrous magnesium sulfate and concentrate under reduced pressure, then purify the residue by column chromatography. Yield: 90%, opaque yellow liquid. 1 H NMR (300MHz, CDCl3)δ: 8.32-8.27(m, 2H), 7.64-7.55(m, 2H), 7.10(s, 1H), 6.00-5.98(m, 1H), 4.04(s, 3H). (2) Synthesis of 1-(1-bromo-4-methoxynaphthalen-2-yl)-2,2,2-trifluoroethanone 1-(1-Bromo-4-methoxynaphthalen-2-yl)-2,2,2-trifluoroethanol (6 mmol) and IBX (18 mmol) are suspended in ethyl acetate (100 mL). The temperature is raised and the reaction is carried out under reflux for 3 hours. When the reaction is complete, the reaction solution is filtered, and the filtrate is concentrated under reduced pressure and then purified by column chromatography. Yield: 89%, yellow solid. 1 H NMR (300MHz, CDCl3) δ: 8.37-8.31 (m, 2H), 7.74-7.63 (m, 2H), 6.80 (s, 1H), 4.04 (s, 3H). (3) Synthesis of 1-(1-(1-bromo-4-methoxynaphthalen-2-yl)-2,2,2-trifluoroethylidene)-2-phenylhydrazine The title compound was synthesized by the procedure described in Preparation 5(1) using 1-(1-bromo-4-methoxynaphthalen-2-yl)-2,2,2-trifluoroethanone (5.88 mmol) as the starting material and then used in the next reaction without further purification. (4) Synthesis of intermediate 18 (5-methoxy-1-phenyl-3-(trifluoromethyl)-1H-benzo[g]indazole) The title compound was synthesized by the procedure described in Preparation 5(2) using 1-(1-(1-bromo-4-methoxynaphthalen-2-yl)-2,2,2-trifluoroethylidene)-2-phenylhydrazine (4.13 mmol) as the starting material. Yield: 44%, pale yellow solid. 1 H NMR (300MHz, CDCl3)δ: 8.47-8.39(m, 1H), 8.31-8.28(m, 1H), 7.72-7.48(m, 5H), 7.39-7.34(m, 1H), 7.21-7.03(m, 1H), 4.02(s, 3H).

[0070] Preparation Example 19: Synthesis of Intermediate 19 (7-fluoro-5-methoxy-3-methyl-1-phenyl-1H-benzo[g]indazole) (1) Synthesis of methyl 6-fluoro-4-hydroxy-2-naphthoate The title compound was synthesized by the procedure described in Preparation 3(1) using 4-fluorobenzaldehyde (16.3 mmol) as the starting material. Yield: overall 26%, white solid. 1 H NMR (300MHz, CDCl3) δ: 8.18 (s, 1H), 7.91-7.79 (m, 1H), 7.42 (s, 1H), 7.33-7.27 (m, 1H), 5.68 (br s, 1H), 3.94 (s, 3H). (2) Synthesis of methyl 6-fluoro-4-methoxy-2-naphthoate The title compound was obtained as a light brown solid by the procedure described in Preparation 3(2) using methyl 6-fluoro-1-hydroxy-3-naphthoate as the starting material, which was used in the next reaction without further purification. (3) Synthesis of methyl 1-bromo-6-fluoro-4-methoxy-2-naphthoate The title compound was synthesized by the procedure described in Preparation 3(3) using methyl 6-fluoro-4-methoxy-2-naphthoate as the starting material. Yield: 92%, pale orange solid. 1 H NMR (300MHz, CDCl3)δ: 8.46-8.41(m, 1H), 7.92-7.87(m, 1H), 7.44-7.39(m, 1H), 7.06(s, 1H), 4.03(s, 3H), 4.01(s, 3H). (4) Synthesis of 1-bromo-6-fluoro-4-methoxy-2-naphthoic acid The title compound was synthesized by the procedure described in Preparation 3(4) using methyl 1-bromo-6-fluoro-4-methoxy-2-naphthoate as the starting material. Yield: 96%, white solid. 1 H NMR (300MHz, CDCl3) δ: 8.54-8.49(m, 1H), 7.94-7.91(m, 1H), 7.47-7.41(m, 1H), 7.25(s, 1H), 4.06(s, 3H). (5) Synthesis of 1-bromo-6-fluoro-N,4-dimethoxy-N-methyl-2-naphthamide The title compound was synthesized by the procedure described in Preparation 4(1) using 1-bromo-6-fluoro-4-methoxy-2-naphthoic acid (3.34 mmol) as the starting material and used in the next reaction without further purification. Yield: 90%, yellow liquid. (6) Synthesis of 1-(1-bromo-6-fluoro-4-methoxynaphthalen-2-yl)ethanone The title compound was synthesized by the procedure described in Preparation 2(2) using 1-bromo-6-fluoro-N,4-dimethoxy-N-methyl-2-naphthamide (13.3 mmol) as the starting material. Yield: 46%, white solid. 1 H NMR (300MHz, CDCl3)δ: 8.35-8.30(m, 1H), 7.90-7.87(m, 1H), 7.44-7.39(m, 1H), 6.75(s, 1H), 4.01(s, 3H), 2.73(s, 3H). (7) Synthesis of 1-(1-(1-bromo-6-fluoro-4-methoxynaphthalen-2-yl)ethylidene)-2-phenylhydrazine The title compound was synthesized by the procedure described in Preparation 5(1) using 1-(1-bromo-6-fluoro-4-methoxynaphthalen-2-yl)ethanone (6.15 mmol) as the starting material and then used in the next reaction without further purification. (8) Synthesis of intermediate 19 (7-fluoro-5-methoxy-3-methyl-1-phenyl-1H-benzo[g]indazole) The title compound was synthesized by the procedure described in Preparation 5(2) using 1-(1-(1-bromo-6-fluoro-4-methoxynaphthalen-2-yl)ethylidene)-2-phenylhydrazine (1.81 mmol) as the starting material. Yield: 25%, brown solid. 1H NMR (300MHz, CDCl3)δ: 8.08-7.90(m, 1H), 7.62-7.48(m, 6H), 7.17-7.03(m, 1H), 6.85(s, 1H), 4.07(s, 3H), 2.64(s, 3H).

[0071] Preparation Example 20: Synthesis of Intermediate 20 (1-(3,5-dichlorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole) (1) Synthesis of 1-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)-2-(3,5-dichlorophenyl)hydrazine The title compound was synthesized by the procedure described in Preparation 5(1) using 1-(1-bromo-4-methoxynaphthalen-2-yl)ethan-1-one (3.6 mmol, Intermediate 4) and 3,5-dichlorophenyl hydrochloride (3.96 mmol) as starting materials and reactants, and then used in the next reaction without further purification. (2) Synthesis of intermediate 20 (1-(3,5-dichlorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole) The title compound was synthesized by the procedure described in Preparation 5(2) using 1-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)-2-(3,5-dichlorophenyl)hydrazine (3.2 mmol) as the starting material. Yield: 24%, brown solid. 1 H NMR (300MHz, DMSO-d6) δ: 8.34 (d, 1H), 7.63 (d, 1H), 7.50 (t, 1H), 7.45 (d, 2H), 7.41 (t, 1H), 7.37 (t, 1H), 6.81 (s, 1H), 3.97 (s, 3H), 2.56 (s, 3H).

[0072] Preparation Example 21: Synthesis of Intermediate 21 (Methyl 4-(5-methoxy-3-methyl-1H-benzo[g]indazol-1-yl)benzoate) (1) Synthesis of methyl 4-(2-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)hydrazinyl)benzoate The title compound was synthesized by the procedure described in Preparation 5(1) using 1-(1-bromo-4-methoxynaphthalen-2-yl)ethan-1-one (7.2 mmol, Intermediate 4) and methyl 4-hydrazinylbenzoate hydrochloride (7.92 mmol) as starting materials and reactants, and then used in the next reaction without further purification. (2) Synthesis of intermediate 21 (methyl 4-(5-methoxy-3-methyl-1H-benzo[g]indazol-1-yl)benzoate) The title compound was synthesized by the procedure described in Preparation 5(2) using methyl 4-(2-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)hydrazinyl)benzoate (3.99 mmol) as the starting material and then used in the next reaction without further purification. Yield: 22%, light brown solid.

[0073] Preparation Example 22: Synthesis of Intermediate 22 (5-methoxy-3-methyl-1-(naphthalen-1-yl)-1H-benzo[g]indazole) (1) Synthesis of 1-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)-2-(naphthalen-1-yl)hydrazine The title compound was synthesized by the procedure described in Preparation 5(1) using 1-(1-bromo-4-methoxynaphthalen-2-yl)ethan-1-one (2.1 mmol, Intermediate 4) and 1-naphthylhydrazine hydrochloride (2.31 mmol) as starting materials and reactants, and then used in the next reaction without further purification. (2) Synthesis of intermediate 22 (5-methoxy-3-methyl-1-(naphthalen-1-yl)-1H-benzo[g]indazole) The title compound was synthesized by the procedure described in Preparation 5(2) using 1-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)-2-(naphthalen-1-yl)hydrazine (1.82 mmol) as the starting material and then used in the next reaction without further purification. Yield: 51%, light brown solid.

[0074] Preparation Example 23: Synthesis of Intermediate 23 (1-(5-chloropyridin-3-yl)-5-methoxy-3-methyl-1H-benzo[g]indazole) (1) Synthesis of 3-(2-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)hydrazinyl)-5-chloropyridine The title compound was synthesized by the procedure described in Preparation 5(1) using 1-(1-bromo-4-methoxynaphthalen-2-yl)ethan-1-one (10.75 mmol, Intermediate 4) and 5-chloro-3-hydrazinopyridine hydrochloride (11.83 mmol) as starting materials and reactants, and then used in the next reaction without further purification. (2) Synthesis of intermediate 23 (1-(5-chloropyridin-3-yl)-5-methoxy-3-methyl-1H-benzo[g]indazole) The title compound was synthesized by the procedure described in Preparation 5(2) using 3-(2-(1-(1-bromo-4-methoxynaphthalen-2-yl)ethylidene)hydrazinyl)-5-chloropyridine (8.12 mmol) as the starting material. Yield: 40%, brown solid. 1 H NMR (300MHz, DMSO-d6)δ:8.60-8.58(m, 1H), 8.39-8.36(m, 1H), 8.05-7.90(m, 1H), 7.80-7 .71(m, 1H), 7.60-7.53(m, 1H), 7.40-7.31(m, 2H), 6.88(s, 1H), 4.08(s, 3H), 2.65(s, 3H).

[0075] Example 1: Synthesis of Compound 1 (1-phenylimidazo[1,2-a]quinoline-4,5-dione) (1) Synthesis of 5-(benzyloxy)-1-phenylimidazo[1,2-a]quinoline Dissolve 4-(benzyloxy)quinolin-2-amine (2 mmol) and sulfur (S8, 4 mmol) in cyclohexane (2 mL) and DMSO (4 mL). Then, add 2-phenylacetaldehyde (4 mmol) and raise the temperature to 120°C for 30 minutes. After the reaction is complete, add H2O to the reaction solution, extract with ethyl acetate, collect the organic layer, dry it with anhydrous magnesium sulfate, concentrate under reduced pressure, and purify it by column chromatography. Yield: 31%, yellow solid. 1 H NMR (300MHz, DMSO-d6) δ: 8.27-8.24 (m, 1H), 7.55-7.27 (m, 12H), 6.95 (s, 1H), 5.28 (s, 2H). (2) Synthesis of 1-phenylimidazo[1,2-a]quinolin-5-ol Dissolve 5-(benzyloxy)-1-phenylimidazo[1,2-a]quinoline (0.8 mmol) in methylene chloride (2 mL). Lower the temperature to 0°C, slowly add BBr3 (1.68 mmol), and gradually warm to room temperature and react for 1 hour. Add H2O to the reaction solution, then extract with ethyl acetate. Purify by recrystallization from methylene chloride and n-hexane. Yield: 66%, brown solid. 1 H NMR (300MHz, DMSO-d6) δ: 8.14-8.12 (d, J=7.0Hz, 1H), 7.51-7.34 (m, 8H), 7.26 (s, 1H), 6.75 (br s, 1H). (3) Synthesis of compound 1 (1-phenylimidazo[1,2-a]quinoline-4,5-dione) Add 1-phenylimidazo[1,2-a]quinolin-5-ol (0.38 mmol) and dissolve in DMF (10 mL). Then, add IBX (0.38 mmol) all at once and react for 2 hours. When the reaction is complete, add saturated sodium bicarbonate solution to terminate the reaction. Extract the reaction solution with ethyl acetate, collect the organic layer, dry it over anhydrous magnesium sulfate, concentrate under reduced pressure, and purify it by column chromatography. Yield: 65%, yellow solid. 1H NMR (300MHz, DMSO-d6) δ: 8.20-8.17 (m, 1H), 7.60-7.50 (m, 5H), 7.46 (s, 1H), 7.44-7.33 (m, 2H), 7.11-7.08 (m, 1H).

[0076] Example 2: Synthesis of Compound 2 (1-(4-fluorophenyl)imidazo[1,2-a]quinoline-4,5-dione) (1) Synthesis of 5-(benzyloxy)-1-(4-fluorophenyl)imidazo[1,2-a]quinoline 4-(benzyloxy)quinolin-2-amine (0.3 mmol, intermediate 1) and sulfur (S8, 0.6 mmol) are added and dissolved in cyclohexane (0.3 mL) and DMSO (0.6 mL). Then, 2-(4-fluorophenyl)acetaldehyde (0.6 mmol) is added, and the temperature is raised to 120°C and reacted for 30 minutes. When the reaction is complete, H2O is added, followed by extraction with ethyl acetate. The organic layer is collected, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography. Yield: 35%, pale yellow solid. 1 H NMR (300MHz, CDCl3) δ: 8.28-8.26 (m, 1H), 7.64-7.20 (m, 13H), 6.94 (s, 1H), 5.28 (s, 2H). (2) Synthesis of 1-(4-fluorophenyl)imidazo[1,2-a]quinolin-5-ol Dissolve 5-(benzyloxy)-1-(4-fluorophenyl)imidazo[1,2-a]quinoline (0.14 mmol) in methylene chloride (3 mL) and lower the temperature to 0°C. Slowly add BBr3 (1.68 mmol) dropwise, gradually raise the temperature to room temperature and react for 1 hour. After adding H2O to terminate the reaction, the reaction solution was extracted with ethyl acetate. Recrystallization with methylene chloride and n-hexane gave a brown solid, which was used in the next reaction without further purification. (3) Synthesis of compound 2 (1-(4-fluorophenyl)imidazo[1,2-a]quinoline-4,5-dione) Dissolve 1-(4-fluorophenyl)imidazo[1,2-a]quinolin-5-ol (0.38 mmol) in DMF (10 mL), add IBX (0.38 mmol) in one portion, and react for 2 hours. When the reaction is complete, add saturated sodium bicarbonate solution to terminate the reaction. Extract the reaction solution with ethyl acetate, collect the organic layer, dry it over anhydrous magnesium sulfate, concentrate under reduced pressure, and purify it by column chromatography. Yield: 49%, orange solid. 1 H NMR (300MHz, DMSO-d6) δ: 8.02-7.99 (m, 1H), 7.60-7.55 (m, 2H), 7.50-7.37 (m, 5H), 6.94-6.92 (m, 1H).

[0077] Example 3: Synthesis of Compound 3 (1-isopropylimidazo[1,2-a]quinoline-4,5-dione) (1) Synthesis of 5-(benzyloxy)-1-isopropylimidazo[1,2-a]quinoline The title compound was synthesized by the procedure described in Example 1(1) using 4-(benzyloxy)quinolin-2-amine (0.3 mmol, Intermediate 1) and 3-methylbutanal (0.6 mmol) as starting materials and reactants. Yield: 41%, yellow solid. 1 H NMR (300MHz, CDCl3)δ: 8.31-8.22(m, 2H), 7.65-7.60(m, 1H), 7.52-7.28(m, 7H) 6.90(s, 1H), 5.28(s, 2H), 3.78-3.69(m, 1H), 1.48(d, J=6.6Hz, 6H). (2) Synthesis of 1-isopropylimidazo[1,2-a]quinolin-5-ol The title compound was synthesized by the procedure described in Example 1(2) using 5-(benzyloxy)-1-isopropylimidazo[1,2-a]quinoline (0.8 mmol) as the starting material and then used in the next reaction without further purification. (3) Synthesis of compound 3 (1-isopropylimidazo[1,2-a]quinoline-4,5-dione) The title compound was synthesized by the procedure described in Example 1(3) using 1-isopropylimidazo[1,2-a]quinolin-5-ol as the starting material. Yield: 17%, orange solid. 1 H NMR (300MHz, CDCl3)δ:8.23-8.21(m, 1H), 7.84-7.76(m, 2H), 7.48-7.39(m, 2H), 3.63-3.56(m, 1H), 1.51(d, J=6.6Hz, 1H).

[0078] Example 4: Synthesis of Compound 4 (1-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]quinoline-4,5-dione) (1) Synthesis of 5-(benzyloxy)-1-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]quinoline The title compound was synthesized by the procedure described in Example 1(1) using 4-(benzyloxy)quinolin-2-amine (0.3 mmol, Intermediate 1) and 2-(4-(trifluoromethyl)phenyl)acetaldehyde (0.6 mmol). Yield: 20%, pale yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.30(dd, J=7.9, 1.3Hz, 1H), 7.75(d, J=8.4Hz, 2H), 7.64(d, J=8.4Hz, 2H), 7.55-7.36(m, 9H), 6.95(s, 1H), 5.30(s, 2H). (2) Synthesis of 1-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]quinolin-5-ol The title compound was synthesized by the procedure described in Example 1(2) using 5-(benzyloxy)-1-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]quinoline (0.8 mmol) as a starting material, and the resulting light brown solid was used in the next reaction without further purification. (3) Synthesis of compound 4 (1-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]quinoline-4,5-dione) The title compound was synthesized by the procedure described in Example 1(3) using 1-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]quinolin-5-ol as the starting material. Yield: 43%, orange solid. 1 H NMR (300MHz, CDCl3)δ: 8.23-8.20(m, 1H), 7.84(d, J=8.2Hz, 2H), 7.68(d, J=8.2Hz, 2H), 7.50-7.37(m, 3H), 7.05-7.02(m, 1H).

[0079] Example 5: Synthesis of Compound 5 (Ethyl 4,5-dioxo-4,5-dihydroimidazo[1,2-a]quinoline-2-carboxylate) (1) Synthesis of Ethyl 5-hydroxyimidazo[1,2-a]quinoline-2-carboxylate The title compound was synthesized by the procedure described in Example 1(2) using ethyl 5-(benzyloxy)imidazo[1,2-a]quinoline-2-carboxylate (0.5 mmol, Intermediate 2) as the starting material, and the resulting solid was used in the next reaction without further purification. (2) Synthesis of compound 5 (ethyl 4,5-dioxo-4,5-dihydroimidazo[1,2-a]quinoline-2-carboxylate) The title compound was synthesized by the procedure described in Example 1(3) using ethyl 5-hydroxyimidazo[1,2-a]quinoline-2-carboxylate (0.5 mmol) as the starting material. Yield: 57%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.37(s, 1H), 8.29-8.26(m, 1H), 7.88-7.86(m, 1H), 7.66-7.55(m, 2H), 4.46(q, J=7.1Hz, 2H), 1.44(t, J=7.1Hz, 3H).

[0080] Example 6: Synthesis of Compound 6 (Ethyl 4,5-dioxo-1-phenyl-4,5-dihydroimidazo[1,2-a]quinoline-2-carboxylate) (1) Synthesis of Ethyl 5-(benzyloxy)-1-bromoimidazo[1,2-a]quinoline-2-carboxylate Dissolve ethyl 5-(benzyloxy)imidazo[1,2-a]quinoline-2-carboxylate (1 mmol, intermediate 2) in acetonitrile (10 mL). After stirring for 5 minutes, add N-bromosuccinimide (1.1 mmol) and react at room temperature for 12 hours. After the reaction is complete, concentrate under reduced pressure to remove the solvent and purify by column chromatography. Yield: 59%, dark brown solid. 1 H NMR (300MHz, DMSO-d6) δ:9.50(d, J=8.6Hz, 1H), 8.32(d, J=8.2Hz, 1H), 7.71-7.68(m, 1H), 7.58-7.34(m, 6H), 6.60(s, 1H), 5.26(s, 2H), 4.48(q, J=7.2Hz, 2H), 1.47(t, J=7.2Hz, 3H). (2) Synthesis of Ethyl 5-(benzyloxy)-1-phenylimidazo[1,2-a]quinoline-2-carboxylate Ethyl 5-(benzyloxy)-1-bromoimidazo[1,2-a]quinoline-2-carboxylate (1 mmol), Pd(PPh3)4 (5 mol%), K2CO3 (2.5 mmol) and phenylboronic acid (2 mmol) are dissolved in 1,4-dioxane (9.5 mL) and H2O (0.5 mL) and reacted at 100° C. When the reaction is complete, 50 mL of water is added to the reaction solution, followed by extraction with ethyl acetate, drying the organic layer over anhydrous magnesium sulfate, concentrating under reduced pressure, and purifying by column chromatography. Yield: 92%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.27-8.25(m, 1H), 7.58-7.39(m, 10H), 7.25-7.16(m, 2H), 6.95(s, 1H), 5.29(s, 2H), 4.27(q, J=7.1Hz, 2H), 1.23(t, J=7.1Hz, 3H). (3) Synthesis of Ethyl 5-hydroxy-1-phenylimidazo[1,2-a]quinoline-2-carboxylate The title compound was synthesized by the procedure described in Example 1(2) using ethyl 5-(benzyloxy)-1-phenylimidazo[1,2-a]quinoline-2-carboxylate as the starting material, and the resulting light brown solid was used in the next reaction without further purification. (4) Synthesis of compound 6 (ethyl 4,5-dioxo-1-phenyl-4,5-dihydroimidazo[1,2-a]quinoline-2-carboxylate) The title compound was synthesized by the procedure described in Example 1(3) using ethyl 5-hydroxy-1-phenylimidazo[1,2-a]quinoline-2-carboxylate (0.5 mmol) as the starting material. Yield: 54%, deep yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.23-8.21(m, 1H), 7.65-7.57(m, 3H), 7.51-7.48(m, 2H), 7 .40-7.33(m, 2H), 6.81-6.78(m, 1H), 4.28(q, J=7.1Hz, 2H) 1.25(t, J=7.1Hz, 3H).

[0081] Example 7: Synthesis of Compound 7 (N,N-dimethyl-4,5-dioxo-1-phenyl-4,5-dihydroimidazo[1,2-a]quinoline-2-carboxamide) (1) Synthesis of 4,5-dioxo-1-phenyl-4,5-dihydroimidazo[1,2-a]quinoline-2-carboxylic acid Ethyl 4,5-dioxo-1-phenyl-4,5-dihydroimidazo[1,2-a]quinoline-2-carboxylate (2 mmol, compound 5) and lithium hydroxide (4 mmol) were dissolved in 1,4-dioxane (10 mL) and HO (10 mL), and then reacted for 12 hours at 0° C. After completion of the reaction, the reaction solution was adjusted to pH 1 with 3M aqueous hydrochloric acid, and 100 mL of water was added and filtered to obtain a white solid, which was dried and used in the next reaction without further purification. (2) Synthesis of compound 7 (N,N-dimethyl-4,5-dioxo-1-phenyl-4,5-dihydroimidazo[1,2-a]quinoline-2-carboxamide) Dissolve 4,5-dioxo-1-phenyl-4,5-dihydroimidazo[1,2-a]quinoline-2-carboxylic acid (1 mmol), HATU (1.1 mmol), diisomethylpropylethylamine (1.2 mmol) and dimethylamine (1.3 mmol) in dimethylformamide (10 mL). After reacting at room temperature for 12 hours, add water to the reaction solution to terminate the reaction, and extract with ethyl acetate. The organic layer is dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The product is purified by column chromatography. Yield: 90%, deep yellow solid. 1 H NMR (300MHz, CDCl3)δ: 7.69-7.52(m, 7H), 7.39-7.34(m, 1H), 7.24-7.22(m, 1H), 6.81-6.79(m, 1H), 3.21(s, 3H), 3.03(s, 3H).

[0082] Example 8: Synthesis of Compound 8 (N-methyl-4,5-dioxo-1-phenyl-4,5-dihydroimidazo[1,2-a]quinoline-2-carboxamide) The title compound was synthesized by the procedure described in Example 6(2) using 4,5-dioxo-1-phenyl-4,5-dihydroimidazo[1,2-a]quinoline-2-carboxylic acid (1 mmol) prepared in Example 7(1) and methylamine ethanol solution (1.3 mmol). Yield: 50%, deep yellow solid. 1 H NMR (300MHz, CDCl3)δ:7.69-7.65(m, 3H), 7.56-7.50(m, 3H), 7.38-7.33(m, 1H), 7.27-7.22(m, 1H), 6.76-6.73(m, 1H)2.92(s, 3H).

[0083] Example 9: Synthesis of Compound 9 (3-methyl-1-phenyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 3-methyl-1-phenyl-1H-benzo[g]indazol-5-ol The title compound was synthesized by the procedure described in Example 1(2) using Intermediate 5 as the starting material. Yield: 80%, light brown solid. 1H NMR (300MHz, CDCl3) δ: 8.33-8.31 (m, 1H), 7.63-7.51 (m, 7H), 7.37-7.32 (m, 1H), 6.96 (s, 3H), 5.33 (br s, 1H), 2.61 (s, 3H). (2) Synthesis of Compound 9 (3-methyl-1-phenyl-1H-benzo[g]indazole-4,5-dione) The title compound was synthesized by the procedure described in Example 1(3) using 3-methyl-1-phenyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 70%, yellow solid. 1 H NMR (300MHz, CDCl3)δ: 8.19-8.16(m, 1H), 7.64-7.62(m, 3H), 7.56-7.51(m, 2H), 7.46-7.31(m, 2H), 6.89-6.86(m, 1H), 2.63(s, 3H).

[0084] Example 10: Synthesis of Compound 10 (3-isopropyl-1-phenyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 5-methoxy-1-phenyl-1H-benzo[g]indazole-3-carbaldehyde (5-Methoxy-1-phenyl-1H-benzo[g]indazol-3-yl)methanol (26.17 mmol, intermediate 6) is dissolved in methylene chloride (100 mL). PCC (26.17 mmol) and Celite (5.64 g) are added to the reaction solution and reacted for 30 minutes. When the reaction is complete, water is added to the reaction solution and extracted with methylene chloride. The extract is washed with brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography. Yield: 66%, light brown solid. 1H NMR (300MHz, CDCl3)δ: 10.22(s, 1H), 8.28(d, J=8.2Hz, 1H), 7.49-7.46(m, 5H), 7.44-7.36(m, 2H), 7.25(t, J=7.8Hz, 1H), 6.96(s, 1H), 4.02(s, 3H). (2) Synthesis of 1-(5-methoxy-1-phenyl-1H-benzo[g]indazol-3-yl)ethan-1-ol Dissolve 5-methoxy-1-phenyl-1H-benzo[g]indazole-3-carbaldehyde (9.59 mmol) in THF. Lower the temperature below 0°C, slowly add methylmagnesium bromide solution (24 mmol, 3M solution in THF), and react for 5 hours. When the reaction is complete, add saturated aqueous ammonium chloride solution to the reaction solution to terminate the reaction, and extract with ethyl acetate. Wash the extract with salt water, dry over anhydrous magnesium sulfate, concentrate under reduced pressure, and purify by column chromatography. Yield: 92%, pale yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.36(d, J=8.2Hz, 1H), 7.53-7.48(m, 7H), 7.31-7.28 (m, 1H), 7.12 (m, 1H), 5.41-5.39 (m, 1H), 4.05 (s, 3H), 1.78 (d, J=6.4Hz, 3H). (3) Synthesis of 1-(5-methoxy-1-phenyl-1H-benzo[g]indazol-3-yl)ethan-1-one The title compound was synthesized by the procedure described in Example 10(1) using the 1-(5-methoxy-1-phenyl-1H-benzo[g]indazol-3-yl)ethan-1-ol prepared above as the starting material. Yield: 80%, pale yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.40(d, J=2.8Hz, 1H), 7.73(s, 1H), 7.63-7.57(m, 5H), 7. 56-7.51(m, 1H), 7.48-7.44(m, 1H), 7.36-7.34(m, 1H), 4.05(s, 3H), 2.77(s, 3H). (4) Synthesis of 5-methoxy-1-phenyl-3-(prop-1-en-2-yl)-1H-benzo[g]indazole Dissolve methyltriphenylphosphonium bromide (35.3 mmol) in THF (50 mL). After lowering the temperature to -78°C, add n-butyllithium solution (35.3 mmol, 2.5 M solution in hexane) dropwise and react for 2 hours. At the same temperature, add 1-(5-methoxy-1-phenyl-1H-benzo[g]indazol-3-yl)ethan-1-one (7.06 mmol) in THF (20 mL) and react at room temperature while slowly increasing the temperature. When the reaction is complete, add saturated aqueous ammonium chloride solution to the reaction solution to terminate it, and extract with ethyl acetate. The extract is washed with salt water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography. Yield: 95%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.38(d, J=2.9Hz, 1H), 7.57-7.50(m, 6H), 7.35-7.3 0(m, 1H), 7.22(s, 1H), 5.76(s, 1H), 5.47(s, 1H), 4.09(s, 3H), 2.39(s, 3H). (5) Synthesis of 3-isopropyl-5-methoxy-1-phenyl-1H-benzo[g]indazole Dissolve 5-methoxy-1-phenyl-3-(prop-1-en-2-yl)-1H-benzo[g]indazole (6.71 mmol) and Pd / C (5 mol%) in methanol (50 mL). Fill the reaction vessel with hydrogen gas and stir overnight at room temperature. When the reaction is complete, filter through Celite, concentrate the filtrate under reduced pressure, and purify by column chromatography. Yield: 40%, white solid. 1 H NMR (300MHz, CDCl3)δ:8.37(d, J=2.8Hz, 1H), 7.62-7.48(m, 7H), 7.35-7.30(m , 1H), 6.86(s, 1H), 4.09(s, 3H) 3.54-3.43(m, 1H), 1.56-1.53(d, J=6.5Hz, 6H). (6) Synthesis of 3-isopropyl-1-phenyl-1H-benzo[g]indazol-5-ol The title compound was synthesized by the procedure described in Example 1(2) using 3-isopropyl-5-methoxy-1-phenyl-1H-benzo[g]indazole as the starting material. Yield: 95%, light brown solid. 1 H NMR (300MHz, CDCl3)δ:8.21(d, J=8.2Hz, 1H), 7.60-7.49(m, 7H), 7.33-7.29(m, 1H), 6.97(s, 1H), 6.67(s, 1H), 3.39-3.32(m, 1H), 1.46-1.44(d, J=6.5Hz, 6H). (7) Synthesis of compound 10 (3-isopropyl-1-phenyl-1H-benzo[g]indazole-4,5-dione) The title compound was synthesized by the procedure described in Example 1(3) using 3-isopropyl-1-phenyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 96%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.15(d, J=7.7Hz, 1H), 7.62-7.61(m, 3H), 7.55-7.53(m, 2H), 7.40 (t, J=7.6Hz, 1H), 7.32(m, 1H), 6.82(d, J=2.6Hz, 1H), 3.57(m, 1H), 1.39(d, J=2.2Hz, 6H).

[0085] Example 11: Synthesis of Compound 11 (3-heptyl-1-phenyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 3-(hept-1-en-1-yl)-5-methoxy-1-phenyl-1H-benzo[g]indazole The title compound was synthesized by the procedure described in Example 9(4) using n-hexyltriphenylphosphonium bromide (35.3 mmol) and 1-(5-methoxy-1-phenyl-1H-benzo[g]indazol-3-yl)ethan-1-one (7.06 mmol) prepared in Example 10(1). Yield: 95%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.39(d, J=8.2Hz, 1H), 7.66-7.50(m, 7H), 7.35(t, J=7.6Hz, 1H), 6.97(s, 1H), 6.69(d, J=11.2Hz, 1H), 6.00(m, 1H), 4.09(s, 3H), 2.67(m, 2H), 1.53(m, 2H), 1.48-1.28(m, 4H), 0.88(t, J=5.5Hz, 3H). (2) Synthesis of 3-heptyl-5-methoxy-1-phenyl-1H-benzo[g]indazole The title compound was synthesized by the procedure described in Example 10(5) using 3-(hept-1-en-1-yl)-5-methoxy-1-phenyl-1H-benzo[g]indazole (9.11 mmol) as the starting material. Yield: 96%, white solid. 1 H NMR (300MHz, CDCl3)δ:8.37(d, J=8.2Hz, 1H), 7.62-7.49(m, 7H), 7.33(t, J=7.6Hz, 1H), 6.94(s, 1H), 4.09(s, 3H), 3.03(t, J=7.6Hz, 2H), 1.88(m, 2H), 1.48-1.27(m, 8H), 0.87(t, J=5.5Hz, 3H). (3) Synthesis of 3-heptyl-1-phenyl-1H-benzo[g]indazol-5-ol The title compound was synthesized by the procedure described in Example 1(2) using 3-heptyl-5-methoxy-1-phenyl-1H-benzo[g]indazole as the starting material and used in the next reaction without further purification. (4) Synthesis of compound 11 (3-heptyl-1-phenyl-1H-benzo[g]indazole-4,5-dione) The title compound was synthesized by the procedure described in Example 1(3) using 3-heptyl-1-phenyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 86%, yellow solid. 1 H NMR(300MHz, CDCl3)δ:8.16(d, J=7.6Hz, 1H), 7.64-7.62(m, 3H), 7.55-7.53(m, 2H), 7.43(t, J=7.6Hz, 1H), 7.33(t, J=7.6Hz, 1H), 6.86(d, J=7.6Hz, 1H), 2.99(t, J=7.6Hz, 2H), 1.77(m, 2H), 1.43-1.11(m, 8H), 0.86(t, J=5.9Hz, 3H).

[0086] Example 12: Synthesis of Compound 12 (3-phenethyl-1-phenyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 5-methoxy-1-phenyl-3-styryl-1H-benzo[g]indazole The title compound was synthesized by the procedure described in Example 9(4) using benzyltriphenylphosphonium bromide (47.9 mmol) and 1-(5-methoxy-1-phenyl-1H-benzo[g]indazol-3-yl)ethan-1-one (9.6 mmol) prepared in Example 10(1). Yield: 96%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.39(d, J=7.7Hz, 1H), 7.62-7.51(m, 10H), 7.42-7.34(m, 3H), 7.32-7.24(m, 2H), 7.20(s, 1H), 4.14(s, 3H). (2) Synthesis of 5-methoxy-3-phenethyl-1-phenyl-1H-benzo[g]indazole The title compound was synthesized by the procedure described in Example 10(5) using 5-methoxy-1-phenyl-3-styryl-1H-benzo[g]indazole (9.21 mmol) as the starting material. Yield: 98%, white solid. 1 H NMR (300MHz, CDCl3)δ:8.35(d, J=8.2Hz, 1H), 7.60-7.58(m, 6H), 7.51(t, J=7.6Hz, 1H), 7.35-7.30 (m, 1H), 7.31-7.29(m, 5H), 6.71(s, 1H), 4.00(s, 3H), 3.36(t, J=7.4Hz, 2H), 3.20(t, J=7.4Hz, 2H). (3) Synthesis of 3-phenethyl-1-phenyl-1H-benzo[g]indazol-5-ol The title compound was synthesized by the procedure described in Example 1(2) using 5-methoxy-3-phenethyl-1-phenyl-1H-benzo[g]indazole as the starting material and used in the next reaction without further purification. (4) Synthesis of compound 12 (3-phenethyl-1-phenyl-1H-benzo[g]indazole-4,5-dione) The title compound was synthesized by the procedure described in Example 1(3) using 3-isopropyl-1-phenyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 66%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.17(d, J=7.6Hz, 1H), 7.64-7.62(m, 3H), 7.53-7.52(m, 2H), 7.45(t, J=7.6Hz, 1H), 7 .37-7.29(m, 5H), 7.24(t, J=7.6Hz, 1H), 6.87(d, J=7.6Hz, 1H), 3.30(t, J=7.0Hz, 2H), 3.11(t, J=7.0Hz, 2H).

[0087] Example 13: Synthesis of Compound 13 (1,3-diphenyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of (1-bromo-4-methoxynaphthalen-2-yl)(phenyl)methanone The title compound was synthesized by the procedure described in Preparation 4(2) using 1-bromo-N,4-dimethoxy-N-methyl-2-naphthamide prepared in Preparation 4(1) and phenylmagnesium bromide. Yield: 80%, white solid. 1 H NMR (300MHz, DMSO-d6) δ: 8.35-8.29 (m, 2H), 7.79-7.67 (m, 5H), 7.57-7.54 (m, 2H), 7.05 (s, 1H), 3.97 (s, 3H). (2) Synthesis of 1-((1-bromo-4-methoxynaphthalen-2-yl)(phenyl)methylene)-2-phenylhydrazine The title compound was synthesized by the procedure described in Preparation 5(1) using (1-bromo-4-methoxynaphthalen-2-yl)(phenyl)methanone as the starting material. (3) Synthesis of 5-methoxy-1,3-diphenyl-1H-benzo[g]indazole The title compound was synthesized by the procedure described in Preparation 5(2) using 1-((1-bromo-4-methoxynaphthalen-2-yl)(phenyl)methylene)-2-phenylhydrazine as the starting material. Yield: 50%, light brown solid. 1 H NMR (300MHz, DMSO-d6) δ:8.29(d, J=2.8Hz, 1H), 7.91-7.88(m, 2H), 7.55-7. 36(m, 9H), 7.34-7.28(m, 1H), 7.25-7.19(m, 1H), 6.89(s, 1H), 3.98(s, 3H). (4) Synthesis of 1,3-diphenyl-1H-benzo[g]indazol-5-ol The title compound was synthesized by the procedure described in Example 1(2) using 5-methoxy-1,3-diphenyl-1H-benzo[g]indazole as the starting material. Yield: 90%, light brown solid. 1 H NMR (300MHz, DMSO-d6) δ: 8.20 (d, J=2.9Hz, 1H), 7.89-7.85 (m, 2H), 7.52-7.38 (m, 9H), 7.30-7.28 (m, 1H), 7.23-7.16 (m, 1H), 6.85 (br s, 1H). (5) Synthesis of compound 13 (1,3-diphenyl-1H-benzo[g]indazole-4,5-dione) The title compound was synthesized by the procedure described in Example 1(3) using 1,3-diphenyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 94%, yellow solid. 1 H NMR (300MHz, DMSO-d6) δ: 8.21-8.15 (m, 3H), 7.68-7.61 (m, 5H), 7.48-7.44 (m, 4H), 7.39-7.34 (m, 1H), 6.82 (d, J=1.8Hz, 1H).

[0088] Example 14: Synthesis of Compound 14 (3-(4-fluorophenyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of (1-bromo-4-methoxynaphthalen-2-yl)(4-fluorophenyl)methanone The title compound was synthesized by the procedure described in Preparation 4(2) using 1-bromo-N,4-dimethoxy-N-methyl-2-naphthamide synthesized in Preparation 4(1) and 4-fluorophenylmagnesium bromide. Yield: 80%, white solid. 1 H NMR (300MHz, DMSO-d6) δ: 8.34-8.29 (m, 2H), 7.79-7.65 (m, 5H), 7.56-7.54 (m, 1H), 7.03 (s, 1H), 3.97 (s, 3H). (2) Synthesis of 1-((1-bromo-4-methoxynaphthalen-2-yl)(4-fluorophenyl)methylene)-2-phenylhydrazine The title compound was synthesized by the procedure described in Preparation 5(1) using (1-bromo-4-methoxynaphthalen-2-yl)(4-fluorophenyl)methanone as the starting material. (3) Synthesis of 3-(4-fluorophenyl)-5-methoxy-1-phenyl-1H-benzo[g]indazole The title compound was synthesized by the procedure described in Preparation 5(2) using 1-((1-bromo-4-methoxynaphthalen-2-yl)(4-fluorophenyl)methylene)-2-phenylhydrazine as the starting material. Yield: 45%, light gray solid. 1 H NMR (300MHz, DMSO-d6) δ:8.27(d, J=2.8Hz, 1H), 7.87-7.84(m, 2H), 7.56-7. 39(m, 8H), 7.33-7.28(m, 1H), 7.23-7.21(m, 1H), 6.72(s, 1H), 3.98(s, 3H). (4) Synthesis of 3-(4-fluorophenyl)-1-phenyl-1H-benzo[g]indazol-5-ol The title compound was synthesized by the procedure described in Example 1(2) using 3-(4-fluorophenyl)-5-methoxy-1-phenyl-1H-benzo[g]indazole as the starting material. Yield: 89%, light brown solid. 1 H NMR (300MHz, DMSO-d6) δ:8.23(d, J=2.8Hz, 1H), 7.86-7.82(m, 2H), 7.54-7.34(m, 8H), 7.31-7.28(m, 1H), 7.20-7.18(m, 1H), 6.70(br s, 1H). (5) Synthesis of compound 14 (3-(4-fluorophenyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione) The title compound was synthesized by the procedure described in Example 1(3) using 3-(4-fluorophenyl)-1-phenyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 90%, yellow solid. 1 H NMR (300MHz, DMSO-d6) δ: 8.19-8.17 (m, 3H, ), 7.78-7.60 (m, 5H), 7.48-7.43 (m, 1H), 7.37-7.33 (m, 1H), 7.16-7.11 (m, 2H), 6.87 (d, J=7.7Hz, 1H).

[0089] Example 15: Synthesis of Compound 15 (3-(3,4-difluorophenyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of (1-bromo-4-methoxynaphthalen-2-yl)(3,4-difluorophenyl)methanone The title compound was synthesized by the procedure described in Preparation 4(2) using 1-bromo-N,4-dimethoxy-N-methyl-2-naphthamide synthesized in Preparation 4(1) and 3,4-difluorophenylmagnesium bromide. Yield: 75%, white solid. 1 H NMR (300MHz, DMSO-d6) δ: 8.30-8.26 (m, 2H), 7.76-7.62 (m, 4H), 7.53-7.50 (m, 1H), 7.01 (s, 1H), 3.96 (s, 3H). (2) Synthesis of 1-((1-bromo-4-methoxynaphthalen-2-yl)(3,4-difluorophenyl)methylene)-2-phenylhydrazine The title compound was synthesized by the procedure described in Preparation 5(1) using (1-bromo-4-methoxynaphthalen-2-yl)(3,4-difluorophenyl)methanone as the starting material. (3) Synthesis of 3-(3,4-difluorophenyl)-5-methoxy-1-phenyl-1H-benzo[g]indazole The title compound was synthesized by the procedure described in Preparation 5(2) using 1-((1-bromo-4-methoxynaphthalen-2-yl)(3,4-difluorophenyl)methylene)-2-phenylhydrazine as the starting material. Yield: 40%, light gray solid. 1 H NMR (300MHz, DMSO-d6) δ:8.22(d, J=2.8Hz, 1H), 7.84-7.81(m, 2H), 7.52-7. 34(m, 7H), 7.30-7.28(m, 1H), 7.20-7.17(m, 1H), 6.68(s, 1H), 3.96(s, 3H). (4) Synthesis of 3-(3,4-difluorophenyl)-1-phenyl-1H-benzo[g]indazol-5-ol The title compound was synthesized by the procedure described in Example 1(2) using 3-(3,4-difluorophenyl)-5-methoxy-1-phenyl-1H-benzo[g]indazole as the starting material. Yield: 92%, light brown solid. 1 H NMR (300MHz, DMSO-d6) δ: 8.20 (d, J=2.8Hz, 1H), 7.84-7.80 (m, 2H), 7.50-7.30 (m, 7H), 7.29-7.28 (m, 1H), 7.19-7.16 (m, 1H), 6.63 (br s, 1H). (5) Synthesis of compound 15 (3-(3,4-difluorophenyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione) The title compound was synthesized by the procedure described in Example 1(3) using 3-(3,4-difluorophenyl)-1-phenyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 94%, yellow solid. 1 H NMR (300MHz, DMSO-d6)δ:8.19-8.04(m, 3H), 7.68-7.66(m, 3H), 7.66-7.60(m, 2 H), 7.47-7.44(m, 1H), 7.39-7.33(m, 1H), 7.25-7.22(m, 1H), 6.88-6.86(m, 1H).

[0090] Example 16: Synthesis of Compound 16 (3-(bromomethyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione) The title compound was synthesized by the procedure described in Example 1(3) using 3-(bromomethyl)-1-phenyl-1H-benzo[g]indazol-5-ol prepared in Preparation 7(2) as a starting material. Yield: 46%, yellow solid. 1H NMR (300MHz, CDCl3)δ:8.20(d, J=7.6Hz, 1H), 7.66-7.62(m, 3H), 7.58-7.55(m, 2H) ), 7.48(t, J=7.2Hz, 1H), 7.37(t, J=7.6Hz, 1H), 6.89(d, J=8.2Hz, 1H), 4.80(s, 2H)

[0091] Example 17: Synthesis of Compound 17 (3-((dimethylamino)methyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione) Dissolve 3-(bromomethyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione (3.50 mmol, compound 16) in THF (30 mL). After lowering the temperature to 0°C, add dimethylamine (35.0 mmol), warm to room temperature and stir. When the reaction is complete, add water to the reaction solution to terminate the reaction. Extract the reaction solution with ethyl acetate, wash the extract with brine, dry over anhydrous magnesium sulfate, concentrate under reduced pressure, and purify by column chromatography. Yield: 58%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.16(d, J=7.6Hz, 1H), 7.63-7.61(m, 3H), 7.55-7.52(m, 2H), 7.43 (t, J=7.6Hz, 1H), 7.34(t, J=7.6Hz, 1H), 6.86(d, J=7.6Hz, 1H), 3.91(s, 2H), 2.44(s, 6H).

[0092] Example 18: Synthesis of Compound 18 (3-(methoxymethyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 5-(methoxymethoxy)-3-(methoxymethyl)-1-phenyl-1H-benzo[g]indazole Add NaH (3.65 mmol) to a mixed solvent of methanol (4.86 mmol) and DMF (20 mL), lower the temperature to 0°C, and stir. After stirring for 30 minutes, add 3-(bromomethyl)-5-(methoxymethoxy)-1-phenyl-1H-benzo[g]indazole (2.43 mmol, intermediate 7), and raise the temperature to room temperature to react. After the reaction is complete, add water to the reaction solution to terminate the reaction, and extract with ethyl acetate. The extract is washed with salt water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography. Yield: 95%, pale yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.40(d, J=8.2Hz, 1H), 7.62-7.56(m, 6H), 7.55-7.52(m, 1H), 7.41 -7.37(m, 1H), 7.35(t, J=8.4Hz, 1H), 5.48(s, 2H), 4.91(s, 2H), 3.61(s, 3H), 3.50(s, 3H). (2) Synthesis of 3-(methoxymethyl)-1-phenyl-1H-benzo[g]indazol-5-ol Dissolve 5-(methoxymethoxy)-3-(methoxymethyl)-1-phenyl-1H-benzo[g]indazole (2.31 mmol) in methanol (20 mL). Add 2 drops of concentrated hydrochloric acid while stirring at room temperature, and then increase the temperature to react under reflux. When the reaction is complete, concentrate the reaction solution under reduced pressure, add water, and then extract with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and used in the next reaction without further purification. (3) Synthesis of compound 18 (3-(methoxymethyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione) The title compound was synthesized by the procedure described in Example 1(3) using 3-(methoxymethyl)-1-phenyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 75%, yellow solid. 1H NMR(300MHz, CDCl3)δ:8.16(d, J=7.6Hz, 1H), 7.63-7.61(m, 3H), 7.55-7.52(m, 2H), 7.44 (t, J=7.6Hz, 1H), 7.34(t, J=7.6Hz, 1H), 6.87(d, J=7.6Hz, 1H), 4.86(s, 2H), 3.57(s, 3H).

[0093] Example 19: Synthesis of Compound 19 (3-(isopropoxymethyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 3-(isopropoxymethyl)-5-(methoxymethoxy)-1-phenyl-1H-benzo[g]indazole The title compound was synthesized by the procedure described in Example 18(1) using isopropanol (0.37 mL) and 3-(bromomethyl)-5-(methoxymethoxy)-1-phenyl-1H-benzo[g]indazole (2.43 mmol, Intermediate 7). Yield: 39%, pale yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.40(d, J=8.2Hz, 1H), 7.62-7.58(m, 6H), 7.54-7.49(m, 2H), 7.32(t, J =7.4Hz, 1H), 5.46(s, 2H), 4.97(s, 2H), 3.87-3.84(m, 1H), 3.60(s, 3H), 1.29(d, J=5.9Hz, 6H). (2) Synthesis of 3-(isopropoxymethyl)-1-phenyl-1H-benzo[g]indazol-5-ol The title compound was synthesized by the procedure described in Example 18(2) using 3-(isopropoxymethyl)-5-(methoxymethoxy)-1-phenyl-1H-benzo[g]indazole as the starting material and used in the next reaction without further purification. (3) Synthesis of compound 19 (3-(isopropoxymethyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione) The title compound was synthesized by the procedure described in Example 1(3) using 3-(isopropoxymethyl)-1-phenyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 53%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.16(d, J=7.6Hz, 1H), 7.62-7.60(m, 3H), 7.54-7.53(m, 2H), 7.43(t, J=7.6Hz , 1H), 7.33(t, J=7.6Hz, 1H), 6.84(d, J=7.6Hz, 1H), 4.84(s, 2H), 3.90(m, 1H), 1.27(d, J=6.4Hz, 6H).

[0094] Example 20: Synthesis of Compound 20 (1-isopropyl-3-methyl-1H-benzo[g]indazole-4,5-dione) and Compound 21 (2-isopropyl-3-methyl-2H-benzo[g]indazole-4,5-dione) (1) Synthesis of a mixture of 1-isopropyl-5-methoxy-3-methyl-1H-benzo[g]indazole and 2-isopropyl-5-methoxy-3-methyl-2H-benzo[g]indazole 5-Methoxy-3-methyl-1H-benzo[g]indazole (2.1 mmol, intermediate 8) was dissolved in DMF. After lowering the temperature to 0°C, NaH (3.18 mmol) was added, and the mixture was stirred at room temperature. Then, 2-bromopropane (4.24 mmol) was added and reacted for 8 hours. The reaction was terminated by adding H2O, and the reaction solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a mixture of 1-isopropyl-5-methoxy-3-methyl-1H-benzo[g]indazole and 2-isopropyl-5-methoxy-3-methyl-2H-benzo[g]indazole, which was used in the next reaction without further purification. (2) Synthesis of a mixture of 1-isopropyl-3-methyl-1H-benzo[g]indazol-5-ol and 2-isopropyl-3-methyl-2H-benzo[g]indazol-5-ol A mixture of the title compounds was obtained by the procedure described in Example 1(2) using a mixture of 1-isopropyl-5-methoxy-3-methyl-1H-benzo[g]indazole and 2-isopropyl-5-methoxy-3-methyl-2H-benzo[g]indazole as the starting material, and this mixture was used in the next reaction without further purification. (3) Synthesis of Compound 20 (1-isopropyl-3-methyl-1H-benzo[g]indazole-4,5-dione) and Compound 21 (2-isopropyl-3-methyl-2H-benzo[g]indazole-4,5-dione) A mixture of 1-isopropyl-3-methyl-1H-benzo[g]indazol-5-ol and 2-isopropyl-3-methyl-2H-benzo[g]indazol-5-ol was used as the starting material by the procedure described in Example 1(3) to obtain a mixture of the title compounds, from which compound 20 and compound 21 were separated. (Compound 20) Yield: 7%, yellow solid. 1 H NMR (300MHz, CDCl3)δ: 8.04-8.01(m, 2H), 7.82-7.77(m, 1H), 7.61-7.56(m, 1H), 5.22-5.14(m, 1H), 2.39(s, 3H), 1.51(d, J=5.9Hz, 6H). (Compound 21) Yield: 6%, yellow solid. 1 H NMR (300MHz, CDCl3)δ: 8.11-8.03(m, 2H), 7.66-7.62(m, 1H), 7.45-7.40(m, 1H), 4.54-4.50(m, 1H), 2.65(s, 3H), 1.56(d, J=6.5Hz, 6H).

[0095] Example 21: Synthesis of Compound 22 (1,3-dimethyl-1H-benzo[g]indazole-4,5-dione) and Compound 23 (2,3-dimethyl-2H-benzo[g]indazole-4,5-dione) (1) Synthesis of a mixture of 5-methoxy-1,3-dimethyl-1H-benzo[g]indazole and 5-methoxy-2,3-dimethyl-2H-benzo[g]indazole The mixture of title compounds was obtained by the procedure described in Example 20(1) using 5-methoxy-3-methyl-1H-benzo[g]indazole (2.1 mmol, Intermediate 8) and iodomethane (4.24 mmol), and this mixture was used in the next reaction without further purification. (2) Synthesis of a mixture of 1,3-dimethyl-1H-benzo[g]indazol-5-ol and 2,3-dimethyl-2H-benzo[g]indazol-5-ol A mixture of 5-methoxy-1,3-dimethyl-1H-benzo[g]indazole and 5-methoxy-2,3-dimethyl-2H-benzo[g]indazole was used as the starting material by the procedure described in Example 1(2) to obtain a mixture of the title compounds, which was used in the next reaction without further purification. (3) Synthesis of Compound 22 (1,3-dimethyl-1H-benzo[g]indazole-4,5-dione) and Compound 23 (2,3-dimethyl-2H-benzo[g]indazole-4,5-dione) A mixture of 1,3-dimethyl-1H-benzo[g]indazol-5-ol and 2,3-dimethyl-2H-benzo[g]indazol-5-ol was used as the starting material by the procedure described in Example 1(3) to obtain a mixture of the title compounds, from which compounds 22 and 23 were separated. (Compound 22) Yield: 2%, yellow solid. 1 H NMR (300MHz, CDCl3)δ: 8.25-8.20(m, 1H), 7.83-7.79(m, 1H), 7.76-7.72(m, 1H), 7.56-7.52(m, 1H), 4.26(s, 3H), 2.55(s, 3H). (Compound 23) Yield: 1.5%, yellow solid. 1 H NMR (300MHz, CDCl3)δ: 8.14-8.10(m, 1H), 7.98-7.93(m, 1H), 7.68-7.64(m, 1H), 7.49-7.46(m, 1H), 3.89(s, 3H), 2.66(s, 3H).

[0096] Example 22: Synthesis of Compound 24 (3-((1H-imidazol-1-yl)methyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 3-((1H-imidazol-1-yl)methyl)-5-methoxy-1-phenyl-1H-benzo[g]indazole 3-(Bromomethyl)-5-methoxy-1-phenyl-1H-benzo[g]indazole (0.33 mmol) and imidazole (0.66 mmol) synthesized in Preparation Example 7 (1) are dissolved in DMF. After lowering the temperature to 0°C, NaH (3.18 mmol) is added to the reaction solution, and the temperature is raised to room temperature and reacted for 12 hours. The reaction is terminated by adding H2O, and the reaction solution is extracted with ethyl acetate. The organic layer is dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography. 1 H NMR (300MHz, CDCl3) δ: 8.34 (m, 1H), 7.75 (s, 1H), 7.60-7.50 (m, 7H), 7.34 (m, 1H), 7.10 (m, 2H), 6.45 (m, 1H), 5.55 (s, 2H), 3.95 (s, 3H). (2) Synthesis of 3-((1H-imidazol-1-yl)methyl)-1-phenyl-1H-benzo[g]indazol-5-ol The title compound was obtained by the procedure described in Example 1(2) using 3-((1H-imidazol-1-yl)methyl)-5-methoxy-1-phenyl-1H-benzo[g]indazole as the starting material, which was used in the next reaction without further purification. (3) Synthesis of compound 24 (3-((1H-imidazol-1-yl)methyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 3-((1H-imidazol-1-yl)methyl)-1-phenyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 60%, yellow solid. 1H NMR (300MHz, CDCl3)δ:8.15(m, 1H), 7.78(s, 1H), 7.66-7.64(m, 3H), 7.52-7.50(m, 2H), 7.44(m, 1H), 7.34(m, 1H), 7.22(m, 1H), 7.02(m, 1H), 6.84(m, 1H), 5.44(s, 2H).

[0097] Example 23: Synthesis of Compound 25 (1-(4-fluorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 1-(4-fluorophenyl)-3-methyl-1H-benzo[g]indazol-5-ol The title compound was obtained by the procedure described in Example 1(2) using 1-(4-fluorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole as the starting material, which was used in the next reaction without further purification. (2) Synthesis of compound 25 (1-(4-fluorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 1-(4-fluorophenyl)-3-methyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 40%, yellow solid. 1 H NMR (300MHz, CDCl3) δ: 8.03-7.98 (m, 1H), 7.72-7.68 (m, 2H), 7.55-7.50 (m, 4H), 6.78-6.75 (m, 1H), 2.45 (s, 3H).

[0098] Example 24: Synthesis of Compound 26 (1-(4-chlorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 1-(4-chlorophenyl)-3-methyl-1H-benzo[g]indazol-5-ol The title compound was obtained by the procedure described in Example 1(2) using 1-(4-chlorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole as the starting material, which was used in the next reaction without further purification. (2) Synthesis of compound 26 (1-(4-chlorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 1-(4-chlorophenyl)-3-methyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 44%, yellow solid. 1 H NMR (300MHz, CDCl3)δ: 8.12-8.10(m, 1H), 7.58-7.53(m, 2H), 7.48-7.45(m, 2H), 7.44-7.36(m, 2H), 6.90(s, 1H), 2.56(s, 3H).

[0099] Example 25: Synthesis of Compound 27 (1-(3,5-difluorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 1-(3,5-difluorophenyl)-3-methyl-1H-benzo[g]indazol-5-ol The title compound was obtained by the procedure described in Example 1(2) using 1-(3,5-difluorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole as the starting material, which was used in the next reaction without further purification. (2) Synthesis of compound 27 (1-(3,5-difluorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 1-(3,5-difluorophenyl)-3-methyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 12%, yellow solid. 1H NMR (300MHz, CDCl3) δ: 8.17-8.15 (m, 1H), 7.51-7.44 (m, 2H), 7.13-7.08 (m, 3H), 6.99-6.97 (m, 1H), 2.59 (s, 3H).

[0100] Example 26: Synthesis of Compound 28 (1-(2,4-dichlorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 1-(2,4-dichlorophenyl)-3-methyl-1H-benzo[g]indazol-5-ol The title compound was obtained by the procedure described in Example 1(2) using 1-(2,4-dichlorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole as the starting material, which was used in the next reaction without further purification. (2) Synthesis of compound 28 (1-(2,4-dichlorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 1-(2,4-dichlorophenyl)-3-methyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 32%, yellow solid. 1 H NMR (300MHz, CDCl3)δ: 8.17-8.15(m, 1H), 7.69(s, 1H), 7.60-7.54(m, 2H), 7.50-7.40(m, 2H), 6.72-6.70(m, 1H), 2.61(s, 3H).

[0101] Example 27: Synthesis of Compound 29 (3-methyl-1-p-tolyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 3-methyl-1-p-tolyl-1H-benzo[g]indazol-5-ol The title compound was obtained by the procedure described in Example 1(2) using 5-methoxy-3-methyl-1-p-tolyl-1H-benzo[g]indazole as the starting material, which was used in the next reaction without further purification. (2) Synthesis of compound 29 (3-methyl-1-p-tolyl-1H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 3-methyl-1-p-tolyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 27%, yellow solid. 1 H NMR (300MHz, CDCl3) δ: 8.12-8.10 (m, 1H), 7.40-7.32 (m, 6H), 6.90-6.88 (m, 1H), 2.58 (s, 3H), 2.51 (s, 3H).

[0102] Example 28: Synthesis of Compound 30 (3-methyl-1-(pyridin-2-yl)-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 3-methyl-1-(pyridin-2-yl)-1H-benzo[g]indazol-5-ol The title compound was obtained by the procedure described in Example 1(2) using 5-methoxy-3-methyl-1-(pyridin-2-yl)-1H-benzo[g]indazole as the starting material, which was used in the next reaction without further purification. (2) Synthesis of Compound 30 (3-methyl-1-(pyridin-2-yl)-1H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 3-methyl-1-(pyridin-2-yl)-1H-benzo[g]indazol-5-ol as the starting material. Yield: 21%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.69-8.66(m, 1H), 8.20-8.14(m, 1H), 8.09-8.06(m, 1H), 7.78-7 .74(m, 1H), 7.59-7.56(m, 1H), 7.46-7.42(m, 2H), 7.08-6.94(m, 1H), 2.66-2.63(s, 3H).

[0103] Example 29: Synthesis of Compound 31 (3-methyl-1-(pyridin-3-yl)-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 3-methyl-1-(pyridin-3-yl)-1H-benzo[g]indazol-5-ol The title compound was obtained by the procedure described in Example 1(2) using 5-methoxy-3-methyl-1-(pyridin-3-yl)-1H-benzo[g]indazole as the starting material, which was used in the next reaction without further purification. (2) Synthesis of Compound 31 (3-methyl-1-(pyridin-3-yl)-1H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 3-methyl-1-(pyridin-3-yl)-1H-benzo[g]indazol-5-ol as the starting material. Yield: 27%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.90-8.86(m, 2H), 8.25-8.21(m, 1H), 7.97-7.94(m, 1H), 7.66 -7.62(m, 1H), 7.52-7.49(m, 1H), 7.43-7.40(m, 1H), 6.90-6.88(m, 1H), 2.65(s, 3H).

[0104] Example 30: Synthesis of Compound 32 (1-(2,4-difluorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 1-(2,4-difluorophenyl)-3-methyl-1H-benzo[g]indazol-5-ol The title compound was obtained by the procedure described in Example 1(2) using 1-(2,4-difluorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole as the starting material, which was used in the next reaction without further purification. (2) Synthesis of Compound 32 (1-(2,4-difluorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 1-(2,4-difluorophenyl)-3-methyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 27%, yellow solid. 1 H NMR (300MHz, CDCl3)δ: 8.14-8.12(m, 1H), 7.67-7.60(m, 1H), 7.48-7.41(m, 2H), 7.19-7.12(m, 2H), 6.85-6.83(m, 1H), 2.58(s, 3H).

[0105] Example 31: Synthesis of Compound 33 (1-phenyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 1-phenyl-1H-benzo[g]indazol-5-ol The title compound was obtained by the procedure described in Example 1(2) using 5-methoxy-1-phenyl-1H-benzo[g]indazole as the starting material, which was used in the next reaction without further purification. (2) Synthesis of compound 33 (1-phenyl-1H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 1-phenyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 30%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.23(s, 1H), 8.20-8.17(m, 1H), 7.64-7.63(m, 3H), 7 .54-7.50(m, 2H), 7.47-7.42(m, 1H), 7.37-7.32(m, 1H), 6.90-6.87(m, 1H).

[0106] Example 32: Synthesis of Compound 34 (1-phenyl-3-(trifluoromethyl)-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 1-phenyl-3-(trifluoromethyl)-1H-benzo[g]indazol-5-ol The title compound was obtained by the procedure described in Example 1(2) using 5-methoxy-1-phenyl-3-(trifluoromethyl)-1H-benzo[g]indazole as the starting material, which was used in the next reaction without further purification. (2) Synthesis of Compound 34 (1-phenyl-3-(trifluoromethyl)-1H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 1-phenyl-3-(trifluoromethyl)-1H-benzo[g]indazol-5-ol as the starting material. Yield: 19%, yellow solid. 1 H NMR (300MHz, CDCl3) δ: 8.23-8.20 (m, 1H), 7.68-7.66 (m, 3H), 7.56-7.48 (m, 3H), 7.41-7.36 (m, 1H), 6.89-6.87 (m, 1H).

[0107] Example 33: Synthesis of Compound 35 (7-fluoro-3-methyl-1-phenyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 7-fluoro-3-methyl-1-phenyl-1H-benzo[g]indazol-5-ol The title compound was obtained by the procedure described in Example 1(2) using 7-fluoro-5-methoxy-3-methyl-1-phenyl-1H-benzo[g]indazole as the starting material, which was used in the next reaction without further purification. (2) Synthesis of compound 35 (7-fluoro-3-methyl-1-phenyl-1H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 7-fluoro-3-methyl-1-phenyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 29%, yellow solid. 1H NMR (300MHz, CDCl3)δ:7.85-7.82(m, 1H), 7.63-7.59(m, 3H), 7.58-7.46(m, 2H), 7.26-7.25(m, 1H), 7.09-7.04(m, 1H), 6.88-6.82(m, 1H), 2.61(s, 3H).

[0108] Example 34: Synthesis of Compound 36 (1-(3,5-dichlorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 1-(4-chlorophenyl)-3-methyl-1H-benzo[g]indazol-5-ol The title compound was obtained by the procedure described in Example 1(2) using 1-(3,5-dichlorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole (Intermediate 20) as the starting material, which was used in the next reaction without further purification. (2) Synthesis of compound 36 (1-(3,5-dichlorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 1-(3,5-dichlorophenyl)-3-methyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 59%, yellow solid. 1 H NMR (300MHz, CDCl3) δ: 8.16 (d, 1H), 7.62 (s, 1H), 7.49 (m, 4H), 6.98 (d, 1H), 2.62 (s, 3H).

[0109] Example 35: Synthesis of Compound 37 (4-(3-methyl-4,5-dioxo-4,5-dihydro-1H-benzo[g]indazol-1-yl)benzoic acid) (1) Synthesis of 4-(5-hydroxy-3-methyl-1H-benzo[g]indazol-1-yl)benzoic acid The title compound was obtained by the procedure described in Example 1(2) using methyl 4-(5-methoxy-3-methyl-1H-benzo[g]indazol-1-yl)benzoate as the starting material, which was used in the next reaction without further purification. (2) Synthesis of compound 37 (4-(3-methyl-4,5-dioxo-4,5-dihydro-1H-benzo[g]indazol-1-yl)benzoic acid) The title compound was obtained by the procedure described in Example 1(3) using 4-(5-hydroxy-3-methyl-1H-benzo[g]indazol-1-yl)benzoic acid as the starting material. Yield: 48%, yellow solid. 1 H NMR (300MHz, CDCl3)δ: 13.40(s, 1H), 8.19-8.17(m, 2H), 7.97-7.95(m, 1H), 7.73-7.72(m, 2H), 7.49-7.48(m, 2H), 6.80(s, 1H), 2.43(s, 3H).

[0110] Example 36: Synthesis of Compound 38 (3-methyl-1-(naphthalen-1-yl)-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 3-methyl-1-(naphthalen-1-yl)-1H-benzo[g]indazol-5-ol The title compound was obtained by the procedure described in Example 1(2) using 5-methoxy-3-methyl-1-(naphthalen-1-yl)-1H-benzo[g]indazole as the starting material, which was used in the next reaction without further purification. (2) Synthesis of compound 38 (3-methyl-1-(naphthalen-1-yl)-1H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 3-methyl-1-(naphthalen-1-yl)-1H-benzo[g]indazol-5-ol as the starting material. Yield: 43%, yellow solid. 1H NMR (300MHz, CDCl3)δ:8.14-8.13(m, 2H), 8.03-8.01(m, 1H), 7.68-7.66(m, 2H), 7.60-7.59 (m, 1H), 7.52-7.50(m, 1H), 7.41-7.31(m, 2H), 7.12-7.10(m, 1H), 6.44(s, 1H), 2.70(s, 3H).

[0111] Example 37: Synthesis of Compound 39 (1-(5-chloropyridin-3-yl)-3-methyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 1-(5-chloropyridin-3-yl)-3-methyl-1H-benzo[g]indazol-5-ol The title compound was obtained by the procedure described in Example 1(2) using 1-(5-chloropyridin-3-yl)-5-methoxy-3-methyl-1H-benzo[g]indazole as the starting material, which was used in the next reaction without further purification. (2) Synthesis of compound 39 (3-methyl-1-(naphthalen-1-yl)-1H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 3-methyl-1-(naphthalen-1-yl)-1H-benzo[g]indazol-5-ol as the starting material. Yield: 38%, yellow solid. 1 H NMR (300MHz, CDCl3)δ: 8.93-8.91(m, 1H), 8.71-8.69(m, 1H), 8.20-8.15(m, 2H), 7.50-7.45(m, 1H), 7.40-7.32(m, 1H), 6.85(s, 1H), 2.56(s, 3H).

[0112] Example 38: Synthesis of Compound 40 (3-methyl-1-(thiazol-2-yl)-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 2-(5-methoxy-3-methyl-1H-benzo[g]indazol-1-yl)thiazole 5-Methoxy-3-methyl-1H-benzo[g]indazole (1 mmol, intermediate 8), copper iodide (5 mol%), N,N'-dimethylethylenediamine (10 mol%) and potassium phosphate (2 mmol) were dissolved in DMF. The temperature was raised to 110°C and 2-bromothiazole (1.2 mmol) was added to react. The reaction was terminated by adding H2O, and the reaction solution was extracted with ethyl acetate and the remaining water in the organic layer was removed with anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure to give the title compound, which was used in the next reaction without further purification. (2) Synthesis of 3-methyl-1-(thiazol-2-yl)-1H-benzo[g]indazol-5-ol The title compound was obtained by the procedure described in Example 1(2) using 2-(5-methoxy-3-methyl-1H-benzo[g]indazol-1-yl)thiazole as the starting material, and this compound was used in the next reaction without further purification. (3) Synthesis of Compound 40 (3-methyl-1-(thiazol-2-yl)-1H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 3-methyl-1-(thiazol-2-yl)-1H-benzo[g]indazol-5-ol as the starting material. Yield: 38%, yellow solid. 1 H NMR (300MHz, CDCl3)δ: 8.15-8.13(m, 1H), 8.06-8.04(m, 1H), 7.76-7.75(m, 1H), 7.53-7.44(m, 3H), 2.56(s, 3H).

[0113] Example 39: Synthesis of Compound 41 (3-methyl-1-(pyridin-4-yl)-1H-benzo[g]indazole-4,5-dione) and Compound 42 (3-methyl-2-(pyridin-4-yl)-2H-benzo[g]indazole-4,5-dione) (1) Synthesis of a mixture of 5-methoxy-3-methyl-1-(pyridin-4-yl)-1H-benzo[g]indazole and 5-methoxy-3-methyl-2-(pyridin-4-yl)-2H-benzo[g]indazole Dissolve 5-methoxy-3-methyl-1H-benzo[g]indazole (2 mmol, intermediate 8), copper iodide (5 mol%), N,N'-dimethylethylenediamine (10 mol%), potassium phosphate tribasic (4 mmol), and 4-iodopyridine (2.4 mmol) in DMF. Allow to react for 8 hours at 80°C or less. Add H2O to terminate the reaction, extract the reaction solution with ethyl acetate, dry the organic layer over anhydrous magnesium sulfate, and concentrate under reduced pressure to obtain a mixture of 5-methoxy-3-methyl-1-(pyridin-4-yl)-1H-benzo[g]indazole and 5-methoxy-3-methyl-2-(pyridin-4-yl)-2H-benzo[g]indazole. This mixture was used in the next reaction without further purification. (2) Synthesis of a mixture of 3-methyl-1-(pyridin-4-yl)-1H-benzo[g]indazol-5-ol and 3-methyl-2-(pyridin-4-yl)-2H-benzo[g]indazol-5-ol A mixture of 5-methoxy-3-methyl-1-(pyridin-4-yl)-1H-benzo[g]indazole and 5-methoxy-3-methyl-2-(pyridin-4-yl)-2H-benzo[g]indazole was used as the starting material by the procedure described in Example 1(2) to obtain a mixture of the title compounds, which was used in the next reaction without further purification. (3) Synthesis of Compound 41 (3-methyl-1-(pyridin-4-yl)-1H-benzo[g]indazole-4,5-dione) and Compound 42 (3-methyl-2-(pyridin-4-yl)-2H-benzo[g]indazole-4,5-dione) A mixture of 3-methyl-1-(pyridin-4-yl)-1H-benzo[g]indazol-5-ol and 3-methyl-2-(pyridin-4-yl)-2H-benzo[g]indazol-5-ol was used as the starting material by the procedure described in Example 1(3) to obtain a mixture of the title compounds, from which compound 41 and compound 42 were separated. (Compound 41) Yield: overall 6%, yellow solid. 1 H NMR (300MHz, CDCl3)δ: 9.01-9.00(m, 1H), 8.21-8.20(m, 1H), 7.66-7.65(m, 1H), 7.25-7.23(m, 1H), 7.21-7.17(m, 4H), 2.38(s, 3H). (Compound 42) Yield: overall 4%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.87-8.85(m, 1H), 8.19-8.17(m, 1H), 8.12-8.10(m, 1H), 7.73-7.69(m, 1H), 7.60-7.59(m, 2H), 7.55-7.51(m, 1H), 2.85(s, 3H).

[0114] Example 40: Synthesis of Compound 43 (3-methyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 3-methyl-1H-benzo[g]indazol-5-ol The title compound was obtained by the procedure described in Example 1(2) using 5-methoxy-3-methyl-1H-benzo[g]indazole (Intermediate 8) as the starting material, which was used in the next reaction without further purification. (2) Synthesis of compound 43 (3-methyl)-1H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 3-methyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 80%, yellow solid. 1 H NMR (300MHz, DMSO-d6) δ: 13.65 (br s, 1H), 7.98-7.95 (m, 2H), 7.76-7.73 (m, 1H), 7.54-7.50 (m, 1H), 2.54 (s, 3H).

[0115] Example 41: Synthesis of Compound 44 (3-methyl-2-(phenylsulfonyl)-2H-benzo[g]indazole-4,5-dione) 3-Methyl-1H-benzo[g]indazole-4,5-dione (0.95 mmol, compound 43) and dimethylaminopyridine (10 mol%) are dissolved in dichloromethane (10 mL). Trimethylamine (1.5 mmol) and benzenesulfonyl chloride (1.2 mmol) are added under stirring, and the reaction is carried out at room temperature. When the reaction is complete, water is added to terminate the reaction, and the reaction solution is extracted with ethyl acetate. The organic layer is dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography. Yield: 28%, yellow solid. 1 H NMR (300MHz, DMSO-d6) δ: 8.17-8.12 (m, 4H), 7.74-7.70 (m, 2H), 7.65-7.61 (m, 2H), 7.57-7.53 (m, 1H), 3.02 (s, 3H).

[0116] Example 42: Synthesis of Compound 45 (3-methyl-2-(4-fluorophenylsulfonyl)-2H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 41(1) using 3-methyl-1H-benzo[g]indazole-4,5-dione (0.95 mmol, Compound 43) and 4-fluorobenzenesulfonyl chloride (1.2 mmol) as starting materials and reactants. Yield: 35.2%, yellow solid. 1 H NMR (300MHz, CDCl3) δ: 8.19-8.11 (m, 4H), 7.73-7.69 (m, 1H), 7.56-7.52 (m, 1H), 7.33-7.30 (m, 2H), 3.02 (s, 3H).

[0117] Example 43: Synthesis of Compound 46 (2-(2-chlorophenylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 41(1) using 3-methyl-1H-benzo[g]indazole-4,5-dione (0.95 mmol, Compound 43) and 2-chlorobenzenesulfonyl chloride (1.2 mmol) as starting materials and reactants. Yield: 42.3%, yellow solid. 1 H NMR (300MHz, CDCl3) δ: 8.43-8.41 (m, 1H), 8.16-8.14 (m, 1H), 7.95-7.93 (m, 1H), 7.68-7.51 (m, 5H), 3.11 (s, 3H).

[0118] Example 44: Synthesis of Compound 47 (2-(3-chlorophenylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 41(1) using 3-methyl-1H-benzo[g]indazole-4,5-dione (0.71 mmol, Compound 43) and 3-chlorobenzenesulfonyl chloride (0.85 mmol) as starting materials and reactants. Yield: 36.6%, yellow solid. 1 H NMR (300MHz, CDCl3)δ: 8.17-8.14(m, 2H), 8.11-8.10(m, 1H), 8.02-8.00(m, 1H), 7.75-7.68(m, 2H), 7.59-7.53(m, 2H), 3.02(s, 3H).

[0119] Example 45: Synthesis of Compound 48 (3-methyl-2-(pyridin-3-ylsulfonyl)-2H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 41(1) using 3-methyl-1H-benzo[g]indazole-4,5-dione (0.71 mmol, Compound 43) and pyridine-3-sulfonyl chloride (0.85 mmol) as starting materials and reactants. Yield: 28%, yellow solid. 1H NMR (300MHz, CDCl3)δ:8.35-8.34(m, 1H), 8.95-8.93(m, 1H), 8.42-8.39(m, 1H), 8.17-8.11(m, 2H), 7.74-7.70(m, 1H), 7.60-7.56(m, 2H), 3.05(s, 3H).

[0120] Example 46: Synthesis of Compound 49 (2-(4-chlorophenylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 41(1) using 3-methyl-1H-benzo[g]indazole-4,5-dione (0.95 mmol, Compound 43) and 4-chlorobenzenesulfonyl chloride (1.2 mmol) as starting materials and reactants. Yield: 41%, yellow solid. 1 H NMR (300MHz, CDCl3) δ: 8.16-8.12 (m, 2H), 8.08-8.05 (m, 2H), 7.73-7.69 (m, 1H), 7.61-7.55 (m, 3H), 3.01 (s, 3H).

[0121] Example 47: Synthesis of Compound 50 (3-methyl-2-tosyl-2H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 41(1) using 3-methyl-1H-benzo[g]indazole-4,5-dione (0.95 mmol, Compound 43) and 4-toluenesulfonyl chloride (1.2 mmol) as starting materials and reactants. Yield: 41%, yellow solid. 1 H NMR (300MHz, CDCl3)δ: 8.15-8.13(m, 2H), 8.01-7.98(m, 2H), 7.72-7.68(m, 1H), 7.55-7.51(m, 1H), 7.41-7.39(m, 2H), 3.00(s, 3H), 2.45(s, 3H).

[0122] Example 48: Synthesis of Compound 51 (2-(4-methoxyphenylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 41(1) using 3-methyl-1H-benzo[g]indazole-4,5-dione (0.71 mmol, Compound 43) and 4-methoxybenzenesulfonyl chloride (0.85 mmol) as starting materials and reactants. Yield: 64%, yellow solid. 1 H NMR (300MHz, CDCl3)δ: 8.15-8.13(m, 2H), 8.06-8.03(m, 2H), 7.72-7.68(m, 1H), 7.54-7.50(m, 1H), 7.07-7.03(m, 2H), 3.89(s, 3H), 3.00(s, 3H).

[0123] Example 49: Synthesis of compound 52 (methyl 4-(3-methyl-4,5-dioxo-4,5-dihydro-2H-benzo[g]indazol-2-ylsulfonyl)benzoate) The title compound was obtained by the procedure described in Example 41(1) using 3-methyl-1H-benzo[g]indazole-4,5-dione (0.71 mmol, Compound 43) and methyl 4-(chlorosulfonyl)benzoate (0.85 mmol) as starting materials and reactants. Yield: 44.8%, yellow solid. 1 H NMR (300MHz, CDCl3)δ: 8.27-8.18(m, 4H), 8.16-8.12(m, 2H), 7.73-7.69(m, 1H), 7.57-7.53(m, 1H), 3.96(s, 3H), 3.02(s, 3H).

[0124] Example 50: Synthesis of Compound 53 (2-(cyclopropylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 41(1) using 3-methyl-1H-benzo[g]indazole-4,5-dione (0.71 mmol, Compound 43) and cyclopropylsulfonyl chloride (0.85 mmol) as starting materials and reactants. Yield: 74%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.20-8.16(m, 2H), 7.75-7.71(m, 1H), 7.59-7.55(m, 1H), 3.07-3.01(m, 1H), 2.97(s, 3H), 1.61-1.58(m, 2H), 1.32-1.26(m, 2H).

[0125] Example 51: Synthesis of Compound 54 (2-(cyclopentylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 41(1) using 3-methyl-1H-benzo[g]indazole-4,5-dione (0.71 mmol, Compound 43) and cyclopentylsulfonyl chloride (0.85 mmol) as starting materials and reactants. Yield: 26.7%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.20-8.16(m, 2H), 7.75-7.71(m, 1H), 7.59-7.55(m, 1H), 4.27-4.19(m, 1H), 2.99(s, 3H), 2.22-2.13(m, 2H), 2.10-2.01(m, 2H), 1.94-1.84(m, 2H), 1.77-1.68(m, 2H).

[0126] Example 52: Synthesis of Compound 55 (4-(3-methyl-4,5-dioxo-4,5-dihydro-2H-benzo[g]indazol-2-ylsulfonyl)benzonitrile) The title compound was obtained by the procedure described in Example 41(1) using 3-methyl-1H-benzo[g]indazole-4,5-dione (0.71 mmol, Compound 43) and 4-cyanobenzenesulfonyl chloride (0.85 mmol) as starting materials and reactants. Yield: 22.5%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.27-8.25(m, 2H), 8.17-8.15(m, 1H), 8.12-8.10(m, 1H), 7.93-7.91(m, 2H), 7.74-7.71(m, 1H), 7.59-7.55(m, 1H), 3.03(s, 3H).

[0127] Example 53: Synthesis of Compound 56 (3-methyl-2-(4-nitrophenylsulfonyl)-2H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 41(1) using 3-methyl-1H-benzo[g]indazole-4,5-dione (0.94 mmol, Compound 43) and 4-nitrobenzenesulfonyl chloride (1.13 mmol) as starting materials and reactants. Yield: 32%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.47-8.45(m, 2H), 8.36-8.33(m, 2H), 8.17-8.15(m, 1H), 8.12-8.10(m, 1H), 7.75-7.71(m, 1H), 7.59-7.55(m, 1H), 3.05(s, 3H).

[0128] Example 54: Synthesis of Compound 57 (3-methyl-2-(4-(trifluoromethyl)phenylsulfonyl)-2H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 41(1) using 3-methyl-1H-benzo[g]indazole-4,5-dione (0.71 mmol, Compound 43) and 4-(trifluoromethyl)benzenesulfonyl chloride (0.85 mmol) as starting materials and reactants. Yield: 54.8%, yellow solid. 1H NMR (300MHz, CDCl3)δ: 8.28-8.26(m, 2H), 8.17-8.12(m, 2H), 7.90-7.88(m, 2H), 7.74-7.70(m, 1H), 7.58-7.54(m, 1H), 3.03(s, 3H).

[0129] Example 55: Synthesis of Compound 58 (2-(3,4-difluorophenylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 41(1) using 3-methyl-1H-benzo[g]indazole-4,5-dione (0.5 mmol, Compound 43) and 3,4-difluorobenzenesulfonyl chloride (0.6 mmol) as starting materials and reactants. Yield: 20.6%, red-yellow solid. 1 H NMR (300MHz, CDCl3)δ: 8.19-8.12(m, 2H), 8.02-7.94(m, 2H), 7.77-7.71(m, 1H), 7.60-7.52(m, 1H), 7.46-7.39(m, 1H), 3.02(s, 3H).

[0130] Example 56: Synthesis of Compound 59 (2-(2,4-difluorophenylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 41(1) using 3-methyl-1H-benzo[g]indazole-4,5-dione (0.71 mmol, Compound 43) and 2,4-difluorobenzenesulfonyl chloride (0.85 mmol) as starting materials and reactants. Yield: 14.6%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.29-8.23(m, 1H), 8.19-8.15(m, 1H), 8.07-8.01(m, 1H), 7.73 -7.65(m, 1H), 7.59-7.52(m, 1H), 7.19-7.15(m, 1H), 7.04-6.96(m, 1H), 3.08(s, 3H).

[0131] Example 57: Synthesis of Compound 60 (3-methyl-2-(quinolin-8-ylsulfonyl)-2H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 41(1) using 3-methyl-1H-benzo[g]indazole-4,5-dione (0.71 mmol, Compound 43) and quinoline-8-sulfonyl chloride (0.85 mmol) as starting materials and reactants. Yield: 30%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.90-8.89(m, 1H), 8.82-8.80(m, 1H), 8.25-8.19(m, 2H), 8.10-8.08(m, 1H), 7.93-7.91(m, 1H), 7.81-7.77(m, 1H), 7.56-7.50(m, 2H), 7.46-7.44(m, 1H), 3.40(s, 3H).

[0132] Example 58: Synthesis of Compound 61 (3-methyl-2-(1-methyl-1H-imidazol-2-ylsulfonyl)-2H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 41(1) using 3-methyl-1H-benzo[g]indazole-4,5-dione (0.71 mmol, Compound 43) and 1-methylimidazole-2-sulfonyl chloride (0.85 mmol) as starting materials and reactants. Yield: 16%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.18-8.16(m, 1H), 8.09-8.03(m, 1H), 7.73-7.69(m, 1H), 7.58-7.52(m, 1H), 7.23(s, 1H), 7.14(s, 1H), 4.22(s, 3H), 3.10(s, 3H).

[0133] Example 59: Synthesis of Compound 62 (3-methyl-2-(morpholinosulfonyl)-2H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 41(1) using 3-methyl-1H-benzo[g]indazole-4,5-dione (0.71 mmol, Compound 43) and morpholine-4-sulfonyl chloride (0.85 mmol) as starting materials and reactants. Yield: 23.5%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.20-8.18(m, 1H), 8.10-8.08(m, 1H), 7.75-7.72(m, 1H), 7.58-7.55(m, 1H), 3.86-3.84(m, 4H), 3.62-3.60(m, 4H), 2.93(s, 3H).

[0134] Example 60: Synthesis of Compound 63 (1-benzyl-3-methyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 1-benzyl-5-methoxy-3-methyl-1H-benzo[g]indazole The title compound was obtained by the procedure described in Example 20(1) using 5-methoxy-3-methyl-1H-benzo[g]indazole (2.1 mmol, Intermediate 8) and benzyl bromide (4.2 mmol) as starting materials and reactants. Yield: 45%, gray solid. 1 H NMR (300MHz, CDCl3)δ:8.38-8.36(m, 1H), 8.26-8.24(m, 1H), 7.54-7.43(m, 2H), 7.29 -7.21(m, 3H), 7.11-7.09(m, 2H), 6.88(s, 1H), 5.98(s, 2H), 4.05(s, 3H), 2.64(s, 3H). (2) Synthesis of 1-benzyl-3-methyl-1H-benzo[g]indazol-5-ol The mixture of title compounds was obtained by the procedure described in Example 1(2) using 1-benzyl-5-methoxy-3-methyl-1H-benzo[g]indazole as the starting material, and this mixture was used in the next reaction without further purification. (3) Synthesis of Compound 63 (1-benzyl-3-methyl-1H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 1-benzyl-3-methyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 59%, yellow solid. 1 H NMR (300MHz, CDCl3)δ: 8.14-8.12(m, 1H), 7.52-7.50(m, 2H), 7.45-7.30(m, 4H), 7.15-7.13(m, 2H), 5.73(s, 2H), 2.57(s, 3H).

[0135] Example 61: Synthesis of Compound 64 (3-methyl-1-phenethyl-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 5-methoxy-3-methyl-1-phenethyl-1H-benzo[g]indazole The title compound was obtained by the procedure described in Example 20(1) using 5-methoxy-3-methyl-1H-benzo[g]indazole (2 mmol, Intermediate 8) and phenethyl bromide (4 mmol) as starting materials and reactants, and was used in the next reaction without further purification. (2) Synthesis of 3-methyl-1-phenethyl-1H-benzo[g]indazol-5-ol The mixture of title compounds was obtained by the procedure described in Example 1(2) using 5-methoxy-3-methyl-1-phenethyl-1H-benzo[g]indazole as the starting material, and this mixture was used in the next reaction without further purification. (3) Synthesis of compound 64 (3-methyl-1-phenethyl-1H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 3-methyl-1-phenethyl-1H-benzo[g]indazol-5-ol as the starting material. Yield: 20%, yellow solid. 1H NMR (300MHz, CDCl3)δ:8.21-8.19(m, 1H), 7.66-7.61(m, 2H), 7.52-7.48(m, 1H), 7.34 -7.30(m, 2H), 7.25-7.21(m, 3H), 4.72-4.68(m, 2H), 3.30-3.27(m, 2H), 2.55(s, 3H).

[0136] Example 62: Synthesis of Compound 65 (1-(4-fluorophenethyl)-3-methyl-1H-benzo[g]indazole-4,5-dione) and Compound 66 (2-(4-fluorophenethyl)-3-methyl-2H-benzo[g]indazole-4,5-dione) (1) Synthesis of a mixture of 1-(4-fluorophenethyl)-5-methoxy-3-methyl-1H-benzo[g]indazole and 2-(4-fluorophenethyl)-5-methoxy-3-methyl-2H-benzo[g]indazole Using 5-methoxy-3-methyl-1H-benzo[g]indazole (2 mmol, Intermediate 8) and 4-fluorophenethyl bromide (4 mmol) as starting materials and reactants, the procedure described in Example 20(1) was followed to obtain a mixture of the title compounds 1-(4-fluorophenethyl)-5-methoxy-3-methyl-1H-benzo[g]indazole and 2-(4-fluorophenethyl)-5-methoxy-3-methyl-2H-benzo[g]indazole, which was used in the next reaction without further purification. (2) Synthesis of a mixture of 1-(4-fluorophenethyl)-3-methyl-1H-benzo[g]indazol-5-ol and 2-(4-fluorophenethyl)-3-methyl-2H-benzo[g]indazol-5-ol A mixture of 1-(4-fluorophenethyl)-5-methoxy-3-methyl-1H-benzo[g]indazole and 2-(4-fluorophenethyl)-5-methoxy-3-methyl-2H-benzo[g]indazole was used as the starting material by the procedure described in Example 1(2) to obtain a mixture of the title compounds, which was used in the next reaction without further purification. (3) Synthesis of Compound 65 (1-(4-fluorophenethyl)-3-methyl-1H-benzo[g]indazole-4,5-dione) and Compound 66 (2-(4-fluorophenethyl)-3-methyl-2H-benzo[g]indazole-4,5-dione) A mixture of the title compounds was obtained by the procedure described in Example 1(3) using a mixture of 1-(4-fluorophenethyl)-3-methyl-1H-benzo[g]indazol-5-ol and 2-(4-fluorophenethyl)-3-methyl-2H-benzo[g]indazol-5-ol as the starting material, and compound 65 and compound 66 were separated from the mixture. (Compound 65) Yield: 3%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.23-8.21(m, 1H), 7.67-7.59(m, 2H), 7.54-7.50(m, 1H), 7.1 8-7.15(m, 2H), 7.02-6.98(m, 2H), 4.70-4.66(m, 2H), 3.8-3.25(m, 2H), 2.55(s, 3H). (Compound 66) Yield: 2%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.15-8.13(m, 1H), 8.06-8.04(m, 1H), 7.70-7.66(m, 1H), 7.49 -7.45(m, 1H), 7.04-6.94(m, 4H), 4.30-4.27(m, 2H), 3.22-3.19(m, 2H), 2.22(s, 3H).

[0137] Example 63: Synthesis of Compound 67 (3-methyl-1-(3-phenylpropyl)-1H-benzo[g]indazole-4,5-dione) (1) Synthesis of 5-methoxy-3-methyl-1-(3-phenylpropyl)-1H-benzo[g]indazole The title compound was obtained by the procedure described in Example 20(1) using 5-methoxy-3-methyl-1H-benzo[g]indazole (2 mmol, Intermediate 8) and 1-bromo-3-phenylpropane (4 mmol) as starting materials and reactants, and was used in the next reaction without further purification. (2) Synthesis of 3-methyl-1-(3-phenylpropyl)-1H-benzo[g]indazol-5-ol The mixture of title compounds was obtained by the procedure described in Example 1(2) using 5-methoxy-3-methyl-1-(3-phenylpropyl)-1H-benzo[g]indazole as the starting material, and this mixture was used in the next reaction without further purification. (3) Synthesis of compound 67 (3-methyl-1-(3-phenylpropyl)-1H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 3-methyl-1-(3-phenylpropyl)-1H-benzo[g]indazol-5-ol as the starting material. Yield: 32%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.13-8.11(m, 1H), 7.45-7.43(m, 2H), 7.36-7.33(m, 2H), 7.29 -7.20(m, 4H), 4.46-4.40(m, 2H), 2.84-2.80(m, 2H), 2.50(s, 3H), 2.31-2.27(m, 2H).

[0138] Example 64: Synthesis of Compound 68 (3-methyl-1-(4-methylphenethyl)-1H-benzo[g]indazole-4,5-dione) and Compound 69 (3-methyl-2-(4-methylphenethyl)-2H-benzo[g]indazole-4,5-dione) (1) Synthesis of a mixture of 5-methoxy-3-methyl-1-(4-methylphenethyl)-1H-benzo[g]indazole and 5-methoxy-3-methyl-2-(4-methylphenethyl)-2H-benzo[g]indazole Using 5-methoxy-3-methyl-1H-benzo[g]indazole (2 mmol, Intermediate 8) and 4-methylphenethyl bromide (4 mmol) as starting materials and reactants, the procedure described in Example 20(1) was followed to obtain a mixture of the title compounds 5-methoxy-3-methyl-1-(4-methylphenethyl)-1H-benzo[g]indazole and 5-methoxy-3-methyl-2-(4-methylphenethyl)-2H-benzo[g]indazole, which was used in the next reaction without further purification. (2) Synthesis of a mixture of 3-methyl-1-(4-methylphenethyl)-1H-benzo[g]indazol-5-ol and 3-methyl-2-(4-methylphenethyl)-2H-benzo[g]indazol-5-ol A mixture of 5-methoxy-3-methyl-1-(4-methylphenethyl)-1H-benzo[g]indazole and 5-methoxy-3-methyl-2-(4-methylphenethyl)-2H-benzo[g]indazole was used as the starting material by the procedure described in Example 1(2) to obtain a mixture of the title compounds, which was used in the next reaction without further purification. (3) Synthesis of Compound 68 (3-methyl-1-(4-methylphenethyl)-1H-benzo[g]indazole-4,5-dione) and Compound 69 (3-methyl-2-(4-methylphenethyl)-2H-benzo[g]indazole-4,5-dione) A mixture of 3-methyl-1-(4-methylphenethyl)-1H-benzo[g]indazol-5-ol and 3-methyl-2-(4-methylphenethyl)-2H-benzo[g]indazol-5-ol was used as the starting material to obtain a mixture of the title compounds by the procedure described in Example 1(3), from which compound 68 and compound 69 were isolated. (Compound 68) Yield: 10%, yellow solid. 1H NMR (300MHz, CDCl3)δ:8.21-8.19(m, 1H), 7.63(s, 2H), 7.52-7.50(m, 1H), 7 .11(s, 4H), 4.69-4.65(m, 2H), 3.26-3.22(m, 2H), 2.56(s, 2H), 2.31(s, 3H). (Compound 69) Yield: 9%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.16-8.13(m, 1H), 8.07-8.05(m, 1H), 7.69-7.67(m, 1H), 7.46-7.44(m, 1H), 7 .08-7.05(m, 2H), 6.95-6.92(m, 2H), 4.30-4.26(m, 2H), 3.19-3.15(m, 2H), 2.31(s, 3H), 2.16(s, 3H).

[0139] Example 65: Synthesis of Compound 70 (2-(2-fluorophenethyl)-3-methyl-2H-benzo[g]indazole-4,5-dione) (1) Synthesis of 2-(2-fluorophenethyl)-5-methoxy-3-methyl-2H-benzo[g]indazole The title compound was obtained by the procedure described in Example 20(1) using 5-methoxy-3-methyl-1H-benzo[g]indazole (2 mmol, Intermediate 8) and 2-fluorophenethyl bromide (4 mmol) as starting materials and reactants, and was used in the next reaction without further purification. (2) Synthesis of 2-(2-fluorophenethyl)-3-methyl-2H-benzo[g]indazol-5-ol The mixture of title compounds was obtained by the procedure described in Example 1(2) using 2-(2-fluorophenethyl)-5-methoxy-3-methyl-2H-benzo[g]indazole as the starting material, and this mixture was used in the next reaction without further purification. (3) Synthesis of compound 70 (2-(2-fluorophenethyl)-3-methyl-2H-benzo[g]indazole-4,5-dione) The title compound was obtained by the procedure described in Example 1(3) using 2-(2-fluorophenethyl)-3-methyl-2H-benzo[g]indazol-5-ol as the starting material. Yield: 3%, yellow solid. 1 H NMR (300MHz, CDCl3)δ:8.14-8.12(m, 1H), 8.05-8.03(m, 1H), 7.69-7.65(m, 1H), 7.48-7.44(m, 1H), 7.25-7.23(m, 1H), 7.08-6.96(m, 3H), 4.36-4.33(m, 2H), 3.28-3.25(m, 2H), 2.27(s, 3H).

[0140] Experimental Example Experimental Example 1. In vitro NQO1 enzyme activity test In order to measure the NQO1 enzyme activity of the compounds synthesized in the Examples, the experiments were carried out as follows.

[0141] The compounds of the present invention were dissolved in DMSO to prepare a 10 mM stock solution, and then diluted with DMSO to a concentration of 250 μM to prepare a compound sample solution. In the experimental group, the compound sample solution prepared above was added to an enzyme reaction solution in which 50 μl of 1.54 mM cytochrome C solution was added to 900 μL of 50 mM Tris-HCl (pH 7.5) solution containing 0.14% BSA. In the negative control group, DMSO without the compound of the present invention was added to the same enzyme reaction solution. After adding 20 μL of 100 ng / ml NQO1 protein to each of the experimental group and negative control group, 10 μL of 20 mM NADH solution was added to adjust the total volume to 1 mL, and the change in absorbance was observed for 10 minutes at a wavelength of 550 nm using a 1 mL cuvette. The increase in absorbance due to the reduction of cytochrome C was observed for 10 minutes at 550 nm to confirm the reaction rate. The absorbance value was determined, and the activity of the compound of the present invention against NQO1 was expressed as the amount of reduced cytochrome C (nmol reduced cytochrome C / min / μg NQO1 protein). Extinction coefficient of cytochrome C: 21.1 (μmol / mL)-1 cm -1 BSA: bovine serum albumin Tris-HC: Tris(hydroxymethyl)aminomethane hydrochloride (buffer solution) Equipment used = Cary 100 UV-Vis spectrophotometer

[0142] The results are shown in Tables 1 to 8 below.

[0143] [Table 1] TIFF0007607372000014.tif17161

[0144] [Table 2]

[0145] [Table 3]

[0146] [Table 4]

[0147] [Table 5]

[0148] [Table 6]

[0149] [Table 7]

[0150] [Table 8]

[0151] As can be seen from Tables 1 to 8, the amount of reduced cytochrome C increased when treated with the compound of the present invention (experimental group) compared to when not treated (negative control group), confirming that the compound of the present invention is used as a substrate for NQO1 to activate the redox reaction of NQO1.

Claims

1. A compound represented by the following chemical formula 1, or a pharma- ceutically acceptable salt, hydrate, solvate, enantiomer, or tautomer thereof: 【Chemistry 1】 During the ceremony, R １ is H or halo, R2 is absent, H, substituted or unsubstituted C １－１０ Alkyl, substituted or unsubstituted C ６－１０ selected from the group consisting of aryl, and substituted or unsubstituted heteroaryl; R 3 is selected from the group consisting of absent, substituted or unsubstituted C 1-10 alkyl, unsubstituted heteroaryl, and -S(O)(O)R 5 ; with the proviso that R 2 and R 3 cannot simultaneously be absent, alkyl, or heteroaryl; R 4 is selected from the group consisting of H, substituted or unsubstituted C 1-10 alkyl, and substituted or unsubstituted C 6-10 aryl; X1 and X4 are carbon atoms (C), X2 and X3 are nitrogen atoms (N), 【Chemistry 2】 is R １ , R ２ , R ３ , X １ , X ２ , X ３ and X ４ is a single or double bond depending on 【Chemistry 3】 , X １ , X ２ , X ３ and X ４ is absent or a single bond depending on The alkyl may be linear, branched or cyclic and may contain one or more double or triple bonds within the chain; if the alkyl is substituted, the substituents may include halo, C １－６ Alkyloxy, substituted or unsubstituted C ６－１０ Aryl, heteroaryl and -NR ６ R ７ Selected from the group consisting of: When the aryl or heteroaryl is substituted, the substituents are independently selected from the group consisting of １－６ Alkyl, C １－６ Alkyloxy, halo, cyano, nitro, -C(O)OR ５ and C substituted with 1, 2 or 3 halo １－６ selected from the group consisting of alkyl, R ５ is H, C １－６ Alkyl, unsubstituted C ２－５ selected from the group consisting of heterocyclyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; R ６ and R ７ are each independently H or C １－６ is alkyl, The aryl is C ６－１０ The heterocyclyl is a 3- to 7-membered ring group having at least one heteroatom selected from N, O, and S in the ring, and the heteroaryl is a 5- to 10-membered heteroaromatic ring group having one or more heteroatoms selected from N, O, and S in the ring.

2. R ２ is absent, H, unsubstituted C １－１０ Alkyl, substituted or unsubstituted C ６－１０ aryl, and substituted or unsubstituted heteroaryl, where if said aryl or heteroaryl is substituted, the substituents are independently selected from the group consisting of: １－６ selected from the group consisting of alkyl, halo, and -C(O)OR5; R ３ is absent or unsubstituted C １－１０ alkyl or unsubstituted heteroaryl; with the proviso that R 2 and R 3 cannot simultaneously be absent, alkyl, or heteroaryl; R ４ is H, substituted or unsubstituted C １－１０ Alkyl, and substituted or unsubstituted C ６－１０ aryl, where if said alkyl is substituted, the substituents are selected from the group consisting of halo, C １－６ Alkyloxy, unsubstituted C ６－１０ Aryl, heteroaryl and -NR ６ R ７ and when said aryl is substituted, the substituent is halo; R ５ , R 6 and R 7 are each independently H or C １－６ is alkyl, 2. A compound according to claim 1, or a pharma- ceutically acceptable salt, hydrate, solvate, enantiomer or tautomer thereof.

3. The compound of claim 2, or a pharma- ceutically acceptable salt, hydrate, solvate, enantiomer or tautomer thereof, wherein the aryl is phenyl or naphthyl and the heteroaryl is pyridinyl, pyridazinyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl or furanyl.

4. 3-methyl-1-phenyl-1H-benzo[g]indazole-4,5-dione; 3-isopropyl-1-phenyl-1H-benzo[g]indazole-4,5-dione; 3-heptyl-1-phenyl-1H-benzo[g]indazole-4,5-dione; 3-phenethyl-1-phenyl-1H-benzo[g]indazole-4,5-dione; 1,3-diphenyl-1H-benzo[g]indazole-4,5-dione; 3-(4-fluorophenyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione; 3-(3,4-difluorophenyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione; 3-(bromomethyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione; 3-((dimethylamino)methyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione; 3-(methoxymethyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione; 3-(isopropoxymethyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione; 1-isopropyl-3-methyl-1H-benzo[g]indazole-4,5-dione; 2-isopropyl-3-methyl-2H-benzo[g]indazole-4,5-dione; 1,3-Dimethyl-1H-benzo[g]indazole-4,5-dione; 2,3-Dimethyl-2H-benzo[g]indazole-4,5-dione; 3-((1H-imidazol-1-yl)methyl)-1-phenyl-1H-benzo[g]indazole-4,5-dione; 1-(4-fluorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione; 1-(4-chlorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione; 1-(3,5-difluorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione; 1-(2,4-dichlorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione; 3-Methyl-1-p-tolyl-1H-benzo[g]indazole-4,5-dione; 3-Methyl-1-(pyridin-2-yl)-1H-benzo[g]indazole-4,5-dione; 3-Methyl-1-(pyridin-3-yl)-1H-benzo[g]indazole-4,5-dione; 1-(2,4-difluorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione; 1-phenyl-1H-benzo[g]indazole-4,5-dione; 1-phenyl-3-(trifluoromethyl)-1H-benzo[g]indazole-4,5-dione; 7-fluoro-3-methyl-1-phenyl-1H-benzo[g]indazole-4,5-dione; 1-(3,5-dichlorophenyl)-3-methyl-1H-benzo[g]indazole-4,5-dione; 4-(3-methyl-4,5-dioxo-4,5-dihydro-1H-benzo[g]indazol-1-yl)benzoic acid; 3-Methyl-1-(naphthalen-1-yl)-1H-benzo[g]indazole-4,5-dione; 1-(5-chloropyridin-3-yl)-3-methyl-1H-benzo[g]indazole-4,5-dione; 3-Methyl-1-(thiazol-2-yl)-1H-benzo[g]indazole-4,5-dione; 3-Methyl-1-(pyridin-4-yl)-1H-benzo[g]indazole-4,5-dione; 3-Methyl-2-(pyridin-4-yl)-2H-benzo[g]indazole-4,5-dione; and 3-Methyl-1H-benzo[g]indazole-4,5-dione 4. The compound of claim 3 selected from the group consisting of: or a pharma- ceutically acceptable salt, hydrate, solvate, enantiomer or tautomer thereof.

5. R ２ and R3 are each independently absent or substituted alkyl; with the proviso that R 2 and R 3 cannot simultaneously be absent or alkyl; The alkyl substituents are unsubstituted C ６－１０ aryl, or C 6-10 aryl substituted with C 1-6 alkyl or halo; R ４ is unsubstituted C １－１０ is alkyl, 2. A compound according to claim 1, or a pharma- ceutically acceptable salt, hydrate, solvate, enantiomer or tautomer thereof.

6. 6. The compound of claim 5, or a pharma- ceutically acceptable salt, hydrate, solvate, enantiomer or tautomer thereof, wherein said aryl is phenyl or naphthyl.

7. 1-benzyl-3-methyl-1H-benzo[g]indazole-4,5-dione; 3-Methyl-1-phenethyl-1H-benzo[g]indazole-4,5-dione; 1-(4-fluorophenethyl)-3-methyl-1H-benzo[g]indazole-4,5-dione; 2-(4-fluorophenethyl)-3-methyl-2H-benzo[g]indazole-4,5-dione; 3-Methyl-1-(3-phenylpropyl)-1H-benzo[g]indazole-4,5-dione; 3-Methyl-1-(4-methylphenethyl)-1H-benzo[g]indazole-4,5-dione; 3-methyl-2-(4-methylphenethyl)-2H-benzo[g]indazole-4,5-dione; and 2-(2-fluorophenethyl)-3-methyl-2H-benzo[g]indazole-4,5-dione 7. The compound of claim 6 selected from the group consisting of: or a pharma- ceutically acceptable salt, hydrate, solvate, enantiomer or tautomer thereof.

8. R ２ does not exist; R ３ is -S(O)(O)R5; R ４ is unsubstituted C １－１０ is alkyl; R ５ is C １－６ Alkyl, unsubstituted C ２－５ selected from the group consisting of heterocyclyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; wherein when said aryl or heteroaryl is substituted, the substituents are independently selected from the group consisting of: １－６ Alkyl, C １－６ Alkyloxy, halo, nitro, cyano, -C(O)OR ９ and C substituted with 1, 2 or 3 halo １－６ alkyl; R ９ is C １－６ Alkyl, 2. A compound according to claim 1, or a pharma- ceutically acceptable salt, hydrate, solvate, enantiomer or tautomer thereof.

9. The compound of claim 8, or a pharmaceutically acceptable salt, hydrate, solvate, enantiomer or tautomer thereof, wherein the aryl is phenyl or naphthyl, the heteroaryl is pyridinyl, pyridazinyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl or furanyl, and the heterocyclyl is aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl or morpholinyl.

10. 3-Methyl-2-(phenylsulfonyl)-2H-benzo[g]indazole-4,5-dione; 3-methyl-2-(4-fluorophenylsulfonyl)-2H-benzo[g]indazole-4,5-dione; 2-(2-chlorophenylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione; 2-(3-chlorophenylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione; 3-Methyl-2-(pyridin-3-ylsulfonyl)-2H-benzo[g]indazole-4,5-dione; 2-(4-chlorophenylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione; 3-Methyl-2-tosyl-2H-benzo[g]indazole-4,5-dione; 2-(4-methoxyphenylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione; Methyl 4-(3-methyl-4,5-dioxo-4,5-dihydro-2H-benzo[g]indazol-2-ylsulfonyl)benzoate; 2-(cyclopropylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione; 2-(cyclopentylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione; 4-(3-methyl-4,5-dioxo-4,5-dihydro-2H-benzo[g]indazol-2-ylsulfonyl)benzonitrile; 3-Methyl-2-(4-nitrophenylsulfonyl)-2H-benzo[g]indazole-4,5-dione; 3-Methyl-2-(4-(trifluoromethyl)phenylsulfonyl)-2H-benzo[g]indazole-4,5-dione; 2-(3,4-difluorophenylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione; 2-(2,4-difluorophenylsulfonyl)-3-methyl-2H-benzo[g]indazole-4,5-dione; 3-Methyl-2-(quinolin-8-ylsulfonyl)-2H-benzo[g]indazole-4,5-dione; 3-methyl-2-(1-methyl-1H-imidazol-2-ylsulfonyl)-2H-benzo[g]indazole-4,5-dione; and 3-Methyl-2-(morpholinosulfonyl)-2H-benzo[g]indazole-4,5-dione 10. The compound of claim 9 selected from the group consisting of: or a pharma- ceutically acceptable salt, hydrate, solvate, enantiomer or tautomer thereof.

11. A compound represented by the following chemical formula 2, or a salt, enantiomer, or tautomer thereof: 【Chemistry 4】 During the ceremony, R １ is H or halo, R2 is absent, H, substituted or unsubstituted C １－１０ Alkyl, substituted or unsubstituted C ６－１０ selected from the group consisting of aryl, and substituted or unsubstituted heteroaryl; R 3 is selected from the group consisting of absent, substituted or unsubstituted C 1-10 alkyl, unsubstituted heteroaryl, and -S(O)(O)R 5 ; with the proviso that R 2 and R 3 cannot simultaneously be absent, alkyl, or heteroaryl; R 4 is selected from the group consisting of H, substituted or unsubstituted C 1-10 alkyl, and substituted or unsubstituted C 6-10 aryl; X1 and X4 are carbon atoms (C), X2 and X3 are nitrogen atoms (N), 【Chemistry 5】 is R １ , R ２ , R ３ , X １ , X ２ , X ３ and X ４ is a single or double bond depending on 【Chemistry 6】 , X １ , X ２ , X ３ and X ４ is absent or a single bond depending on The alkyl may be linear, branched or cyclic and may contain one or more double or triple bonds within the chain; if the alkyl is substituted, the substituents may include halo, C １－６ Alkyloxy, substituted or unsubstituted C ６－１０ Aryl, heteroaryl, and -NR ６ R ７ Selected from the group consisting of: When the aryl or heteroaryl is substituted, the substituents are independently selected from the group consisting of １－６ Alkyl, C １－６ Alkyloxy, halo, cyano, nitro, -C(O)OR ５ and C substituted with 1, 2 or 3 halo １－６ selected from the group consisting of alkyl, R ５ is H, C １－６ Alkyl, unsubstituted C ２－５ selected from the group consisting of heterocyclyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; R ６ and R ７ are each independently H or C １－６ is alkyl, R ８ is C １－６ Alkyl, or C １－６ Alkoxy-substituted C １－６ is alkyl, The aryl is C ６－１０ The heterocyclyl is a 3- to 7-membered ring group having at least one heteroatom selected from N, O, and S in the ring, and the heteroaryl is a 5- to 10-membered heteroaromatic ring group having one or more heteroatoms selected from N, O, and S in the ring.

12. 5-Methoxy-3-methyl-1-phenyl-1H-benzo[g]indazole; (5-methoxy-1-phenyl-1H-benzo[g]indazol-3-yl)methanol; 3-(bromomethyl)-5-(methoxymethoxy)-1-phenyl-1H-benzo[g]indazole; 5-Methoxy-3-methyl-1H-benzo[g]indazole; 1-(4-fluorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole; 1-(4-chlorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole; 1-(3,5-difluorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole; 1-(2,4-dichlorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole; 5-Methoxy-3-methyl-1-p-tolyl-1H-benzo[g]indazole; 5-Methoxy-3-methyl-1-(pyridin-2-yl)-1H-benzo[g]indazole; 5-Methoxy-3-methyl-1-(pyridin-3-yl)-1H-benzo[g]indazole; 1-(2,4-difluorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole; 5-Methoxy-1-phenyl-1H-benzo[g]indazole; 5-Methoxy-1-phenyl-3-(trifluoromethyl)-1H-benzo[g]indazole; 7-fluoro-5-methoxy-3-methyl-1-phenyl-1H-benzo[g]indazole; 1-(3,5-dichlorophenyl)-5-methoxy-3-methyl-1H-benzo[g]indazole; Methyl 4-(5-methoxy-3-methyl-1H-benzo[g]indazol-1-yl)benzoate; 5-Methoxy-3-methyl-1-(naphthalen-1-yl)-1H-benzo[g]indazole; and 1-(5-chloropyridin-3-yl)-5-methoxy-3-methyl-1H-benzo[g]indazole 12. The compound of claim 11 selected from the group consisting of: or a salt, enantiomer or tautomer thereof.

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