2-phenylimidazo[1,2-a]pyridines and methods of preparation and use

Abstract

The application discloses a 2-phenylimidazo[1,2 α ]pyridine compound, a preparation method and application thereof, and belongs to the technical field of medicines. The compound has an imidazo[1,2-alpha]pyridine as a core skeleton, and is prepared through a three-step method: first, 2-amino pyridine is closed with hydroxyphenylacetophenone to obtain an intermediate LT1-6, then the intermediate LT1-6 is etherified with a bromine carboxylic acid ester to obtain LT7-48, and finally, the LT7-48 is converted into a target product HDDI1-42 containing a hydroxamic acid group through hydroxylamine solution conversion. Activity tests show that the compound has significant HDAC1 inhibitory activity and anti-tumor cell proliferation activity.

Description

Technical Field

[0001] This invention relates to a 2-phenylimidazo[1,2-] α Pyridine antitumor compounds, their preparation methods, pharmaceutical compositions, and pharmaceutical uses belong to the field of pharmaceutical technology. Background Technology

[0002] Imidazolo[1,2-α]pyridine is an important class of nitrogen-containing fused heterocyclic compounds that has attracted widespread attention in medicinal chemistry due to its unique chemical structure and diverse biological activities. Existing literature reports that these skeletal compounds possess various pharmacological activities, including antiviral, antitumor, and anti-neurodegenerative disease activity. Particularly in the antitumor field, researchers have developed some imidazo[1,2-α]pyridine derivatives as protein kinase inhibitors and histone deacetylase (HDAC) inhibitors, showing certain therapeutic potential. However, most existing imidazo[1,2-α]pyridine antitumor compounds still have shortcomings such as insufficient activity improvement, significant toxicity to normal cells, or susceptibility to drug resistance. Therefore, developing novel imidazo[1,2-α]pyridine derivatives with novel structures, higher antitumor activity, and better safety remains of significant clinical importance and research value. Summary of the Invention

[0003] To address the shortcomings of existing technologies, this invention utilizes imidazo[1,2-α]pyridine as the core skeleton and, through multiple rounds of structural modification and alteration, successfully discovered a series of novel 2-phenylimidazo[1,2-α]pyridine antitumor compounds. In subsequent biological activity tests, these 2-phenylimidazo[1,2-α]pyridine compounds exhibited extremely high antitumor activity and hold promise for development into novel antitumor drugs.

[0004] The technical solution of the present invention is as follows: In a first aspect, the present invention provides a 2-phenylimidazo[1,2-α]pyridine compound of general formula I, or its stereoisomer or a pharmaceutically acceptable salt thereof;

[0005] In general formula I, R represents hydrogen, halogen, or unsubstituted C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C5-C6 alkyl, or C6-C6 alkyl. 15 Aryl, C3-C8 heteroaryl, wherein the heteroatom is independently selected from O, S, N or oxidized S or N; R is in 2-phenylimidazo[1,2- α The substitution positions of the pyridine skeleton are at the 6- or 7-position; Z stands for -X-(CH2) n1 -, -X-(CH2) n2 -Ar- or -X-(CH2)n3 -Ar-(CH) n4 -;Z in 2-phenylimidazo[1,2- α The substitution positions of the pyridine skeleton are 3'- or 4'-. n1 represents integers from 2 to 8, and n2, n3, and n4 represent integers from 0 to 3. X represents an oxygen atom; Ar represents unsubstituted C6-C7 aryl, C6-C7 aryl C1-C5 alkyl, C6-C7 aryl C2-C5 alkenyl, C3-C6 heteroaryl, C3-C6 heteroaryl C1-C5 alkyl, and C3-C6 heteroaryl C2-C5 alkenyl.

[0006] The most preferred compound of the above general formula I is one of the following:

[0007] N -hydroxy-2-(4-(imidazo[1,2-) α ]pyridin-2-yl)phenoxy)acetamide (HDDI-1); N -hydroxy-4-(4-(imidazo[1,2-) α ]pyridin-2-yl)phenoxy)butyramide (HDDI-2); N -hydroxy-5-(4-(imidazo[1,2-) α ]Pyridin-2-yl)phenoxy)pentanamide (HDDI-3); N -hydroxy-6-(4-(imidazo[1,2-) α ]pyridin-2-yl)phenoxy)hexamamide (HDDI-4); N -hydroxy-7-(4-(imidazo[1,2-) α ]pyridin-2-yl)phenoxy)heptamide (HDDI-5); N -hydroxy-8-(4-(imidazo[1,2-) α ]pyridin-2-yl)phenoxy)octamide (HDDI-6); N -hydroxy-2-(3-(imidazo[1,2-) α ]pyridin-2-yl)phenoxy)acetamide (HDDI-7); N -hydroxy-4-(3-(imidazo[1,2-) α ]Pyridin-2-yl)phenoxy)butyramide (HDDI-8); N -hydroxy-5-(3-(imidazo[1,2-)α ]Pyridin-2-yl)phenoxy)pentanamide (HDDI-9); N -hydroxy-6-(3-(imidazo[1,2-) α ]Pyridin-2-yl)phenoxy)hexamamide (HDDI-10); N -hydroxy-7-(3-(imidazo[1,2-) α ]Pyridin-2-yl)phenoxy)heptamide (HDDI-11); N -hydroxy-8-(3-(imidazo[1,2-) α ]pyridin-2-yl)phenoxy)octamide (HDDI-12); N -hydroxy-4-((3-(imidazo[1,2-) α ]pyridin-2-yl)phenoxy)methyl)benzamide (HDDI-13); ( E )- N -hydroxy-3-(4-((3-(imidazo[1,2-) α ]pyridin-2-yl)phenoxy)methyl)phenyl)acrylamide (HDDI-14); N -hydroxy-2-(4-(7-methylimidazo[1,2-] α ]pyridin-2-yl)phenoxy)acetamide (HDDI-15); N -hydroxy-4-(4-(7-methylimidazo[1,2-) α ]Pyridin-2-yl)phenoxy)butyramide (HDDI-16); N -hydroxy-5-(4-(7-methylimidazo[1,2-) α ]Pyridin-2-yl)phenoxy)pentanamide (HDDI-17); N -hydroxy-6-(4-(7-methylimidazo[1,2-] α ]pyridin-2-yl)phenoxy)hexamamide (HDDI-18); N -hydroxy-7-(4-(7-methylimidazo[1,2-] α ]Pyridin-2-yl)phenoxy)heptamide (HDDI-19); N -hydroxy-8-(4-(7-methylimidazo[1,2-] α ]Pyridin-2-yl)phenoxy)octamide (HDDI-20); N -hydroxy-2-(3-(7-methylimidazo[1,2-] α ]pyridin-2-yl)phenoxy)acetamide (HDDI-21); N -hydroxy-4-(3-(7-methylimidazo[1,2-) α ]Pyridin-2-yl)phenoxy)butyramide (HDDI-22); N -hydroxy-5-(3-(7-methylimidazo[1,2-] α ]Pyridin-2-yl)phenoxy)pentanamide (HDDI-23); N -hydroxy-6-(3-(7-methylimidazo[1,2-) α ]Pyridin-2-yl)phenoxy)hexamamide (HDDI-24); N -hydroxy-7-(3-(7-methylimidazo[1,2-] α ]Pyridin-2-yl)phenoxy)heptamide (HDDI-25); N -hydroxy-8-(3-(7-methylimidazo[1,2-] α ]pyridin-2-yl)phenoxy)octamide (HDDI-26); N -hydroxy-4-((3-(7-methylimidazo[1,2-) α ]pyridin-2-yl)phenoxy)methyl)benzamide (HDDI-27); ( E )- N -hydroxy-3-(4-((3-(7-methylimidazo[1,2-) α ]Pyridin-2-yl)phenoxy)methyl)phenyl)acrylamide (HDDI-28); 2-(4-(6-bromoimidazole[1,2- α ]pyridin-2-yl)phenoxy)- N - Hydroxyacetamide (HDDI-29); 4-(4-(6-bromoimidazole[1,2- α ]pyridin-2-yl)phenoxy)- N -Hydroxybutyramide (HDDI-30); 5-(4-(6-bromoimidazole[1,2- α ]pyridin-2-yl)phenoxy)- N - Hydroxypentamide (HDDI-31); 6-(4-(6-bromoimidazole[1,2-) α ]pyridin-2-yl)phenoxy)- N - Hydroxyhexamethylene amide (HDDI-32); 7-(4-(6-bromoimidazole[1,2- α ]pyridin-2-yl)phenoxy)- N -Hydroxyheptaamide (HDDI-33); 8-(4-(6-bromoimidazole[1,2- α ]pyridin-2-yl)phenoxy)- N -Hydroxyoctamide (HDDI-34); 2-(3-(6-bromoimidazole[1,2- α ]pyridin-2-yl)phenoxy)- N - Hydroxyacetamide (HDDI-35); 4-(3-(6-bromoimidazole[1,2- α ]pyridin-2-yl)phenoxy)- N -Hydroxybutyramide (HDDI-36); 5-(3-(6-bromoimidazole[1,2- α ]pyridin-2-yl)phenoxy)- N - Hydroxypentamide (HDDI-37); 6-(3-(6-bromoimidazole[1,2-) α ]pyridin-2-yl)phenoxy)- N - Hydroxyhexamethyleneamide (HDDI-38); 7-(3-(6-bromoimidazole[1,2- α ]pyridin-2-yl)phenoxy)- N -Hydroxyheptaamide (HDDI-39); 8-(3-(6-bromoimidazole[1,2- α ]pyridin-2-yl)phenoxy)- N -Hydroxyoctamide (HDDI-40); 4-((3-(7-bromoimidazole[1,2- α ]pyridin-2-yl)phenoxy)methyl)- N - Hydroxybenzamide (HDDI-41); ( E )-3-(4-((3-(7-bromoimidazole[1,2- α ]pyridin-2-yl)phenoxy)methyl)phenyl)- N - Hydroxyacrylamide (HDDI-42).

[0008] The preferred compounds listed above are numbered in parentheses to correspond to the reaction routes below and the compound structures in Table 1.

[0009] In a second aspect, the present invention provides a method for preparing 2-phenylimidazo[1,2-α]pyridine compounds represented by general formula I, comprising the following steps: (a) 2-aminopyridines with different substitutions are reacted with 2-bromo-4'-hydroxyacetophenone or 2-bromo-3'-hydroxyacetophenone in an organic solvent at room temperature to generate intermediate LT1-6; (b) The intermediate LT1-6 obtained in step (a) was reacted with bromocarboxylic acid esters of different structures under alkaline conditions in an aprotic polar solvent by heating to generate the key intermediate LT7-48. (c) The intermediate LT7-48 obtained in step (b) is reacted with hydroxylamine hydrochloride and alkali metal hydroxide in a lower alcohol solvent to convert the methyl ester group into an isohydroxamic acid group, thereby obtaining the target product HDDI1-42.

[0010] Wherein, the bromocarboxylic acid ester mentioned in step (b) is selected from methyl 2-bromoacetate, methyl 4-bromobutyrate, methyl 5-bromopentanoate, methyl 6-bromohexanoate, methyl 7-bromoheptanoate, methyl 4-bromomethylbenzoate, or methyl 4-bromomethylcinnamate.

[0011] The synthesis route is as follows:

[0012] In step (a), the organic solvent is preferably acetone; the reaction is carried out at room temperature for 1-3 hours.

[0013] In step (b), the alkaline conditions are preferably provided by cesium carbonate (Cs2CO3), the aprotic polar solvent is preferably N,N-dimethylformamide (DMF), the reaction temperature is 60~100℃ (preferably 80℃), and the reaction time is 2~4h.

[0014] In step (c), the alkali metal hydroxide is preferably potassium hydroxide (KOH), and the lower alcohol solvent is preferably methanol (MeOH); the reaction is carried out at room temperature for 2-4 hours.

[0015] Those skilled in the art can modify the above steps to increase the yield. They can design synthetic routes based on basic knowledge in the art, such as selecting reactants, reaction solvents, and reaction temperatures. They can also improve the yield by using various protecting groups to avoid side reactions. These conventional protection methods can be found, for example, in T. Green Protecting Groups in Organic Synthesis.

[0016] The specific structure of the target product HDDI1-42 is shown in Table 1 below.

[0017] Table 1 ;

[0018] Thirdly, the present invention provides a pharmaceutical composition comprising a compound represented by the above general formula I, a stereoisomer thereof or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable carriers or excipients.

[0019] Preferably, the pharmaceutical composition is suitable for oral or parenteral administration.

[0020] Fourthly, the present invention provides the use of the compound represented by the above general formula I, its stereoisomers or pharmaceutically acceptable salts thereof in the preparation of medicaments for the prevention or treatment of cancer.

[0021] Preferably, the cancer is selected from leukemia or lung cancer.

[0022] More preferably, the cancer is selected from erythroleukemia, myeloid monocytic leukemia, or lung adenocarcinoma.

[0023] Compared with the prior art, the present invention has the following beneficial effects: (1) This invention provides a novel class of 2-phenylimidazo[1,2-α]pyridine compounds, whose HDAC1 inhibitory activity and anti-tumor cell proliferation activity are significantly superior to the positive control drug SAHA. Among them, compound HDDI-25 inhibits the IC50 of HDAC1. 50 The value was as low as 0.33 nM, and the IC50 value inhibited HEL cell proliferation. 50 The value was as low as 0.0032 μM, which was 180 times and 32.5 times that of SAHA, respectively.

[0024] (2) The compounds of the present invention have low toxicity to normal cells, good selectivity, and higher safety.

[0025] (3) In addition to inhibiting HDAC1, the compound of the present invention can also effectively bind to DNA, which may have a dual-targeting mechanism and help overcome the drug resistance problem of existing HDAC inhibitors.

[0026] (4) The preparation method provided by the present invention has a short route, mild conditions, and simple operation, and is suitable for industrial production.

[0027] (5) The compounds of the present invention have broad prospects for anti-tumor applications and can be used to prepare drugs for the prevention or treatment of cancer. Attached Figure Description

[0028] Figure 1The binding of the active compound to CT-DNA; where A is the UV absorption spectrum of HDDI-11 bound to CT-DNA; B is the UV absorption spectrum of HDDI-25 bound to CT-DNA; C is the UV absorption spectrum of SAHA bound to CT-DNA; D is the fluorescence spectrum of the active compound HDDI-11 bound to CT-DNA; E is the fluorescence spectrum of HDDI-25 bound to CT-DNA; and F is the fluorescence spectrum of SAHA bound to CT-DNA. Detailed Implementation

[0029] It should be noted that the following detailed descriptions are exemplary and intended to provide further explanation of the present invention.

[0030] The terms and definitions used in this article have the following meanings: The "halogen atom" mentioned in this invention includes fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms; The "C" described in this invention 1-6 "Alkyl" refers to a straight-chain or branched alkyl group derived from an alkane containing 1 to 6 carbon atoms by removing one hydrogen atom, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and isohexyl.

[0031] The "C" described in this invention 3-6 "Cycloalkyl" refers to a cyclic alkyl group derived from an alkane with 3 to 6 carbon atoms by removing one hydrogen atom, such as cyclopropyl, cyclobutyl, 1-methylcyclobutyl, cyclopentyl, cyclohexyl, etc. C is preferred. 4-6 cycloalkyl and C 5-6 cycloalkyl; "Aryl" refers to a substituent containing an aromatic ring, such as phenyl or benzyl, with the preferred aryl group containing 5-15 carbon atoms; "Heteroaryl" is an aromatic heterocyclic group, which can be monocyclic or bicyclic. They contain one or more heteroatoms, preferably 1-3 heteroatoms, or even more preferably 1-2 heteroatoms, which are independently selected from O, S and N.

[0032] "Alkenyl", alone or in combination, as referred to herein, means a straight-chain hydrocarbon or a branched hydrocarbon containing 2-6, preferably 2-4, carbon atoms; and containing 1-2 carbon-carbon double bonds, preferably 1 carbon-carbon double bond; "Alkoxy" indicates the group -O-alkyl; The compound of general formula I of the present invention can be prepared into a pharmaceutically acceptable salt by known methods, wherein the salt is a salt prepared by mixing the compound of formula I with an acid or a base; Suitable acid addition salts include, but are not limited to, hydrochlorides, hydrobroms, sulfates, phosphates, acetates, citrates, tartrates, methanesulfonates, benzenesulfonates, trifluoroacetates, etc.

[0033] Suitable base addition salts include, but are not limited to, sodium salts, potassium salts, calcium salts, magnesium salts, ammonium salts, methylamine salts, triethylamine salts, ethanolamine salts, etc.

[0034] In this document, “stereoisomer” refers to the enantiomers, diastereomers and mixtures thereof in any proportion of the compounds of this invention, as well as essentially pure single isomers.

[0035] The substituents described above can also be replaced by one or more substituents. Such substituents include those listed in C. Hansch and A. Leo, Substituent Constants for Correlation Analysis in Chemistry and Biology (1979); preferred substituents include alkyl, alkenyl, alkoxy, hydroxyl, nitro, amino, aminoalkyl, cyano, halogen, carboxyl, thio, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, imino, hydroxyalkyl, aryloxy, arylalkyl, and combinations thereof.

[0036] The compounds of this invention can be formulated into pharmaceutical preparations using conventional methods in the art for oral, parenteral, rectal, or pulmonary administration. Oral preparations may be selected from tablets, capsules, granules, oral solutions, or suspensions; parenteral preparations may be selected from injections or sterile powders for injection; rectal administration may be formulated as suppositories; and pulmonary administration may be formulated as inhalers or sprays. The preparations may contain pharmaceutically acceptable carriers or excipients.

[0037] The therapeutically effective dose of the compounds of this invention can be determined by a clinician based on factors such as the patient's age, health status, and severity of the condition. For example, the daily dose can be 0.1-2000 mg, administered once or in divided doses. The compounds of this invention can also be used in combination with other therapeutically active substances, administered simultaneously, separately, or sequentially.

[0038] To enable those skilled in the art to better understand the technical solution of the present invention, the technical solution of the present invention will be described in detail below with reference to specific embodiments.

[0039] Example 1. 4-(imidazo[1,2- α ]Pyridin-2-yl)phenol (LT-1) 2-Aminopyridine (4.7 g, 50 mmol) was dissolved in 20 mL of acetone, and 2-bromo-4-hydroxyacetophenone (10.75 g, 50 mmol) was added. The reaction was carried out at room temperature for 1 h. After the reaction was completed, the mixture was filtered, and the filter cake was recrystallized from methanol to give a white solid in 82% yield, mp 114-116 °C. 1 H NMR (400 MHz, DMSO- d 6) d 10.17 (s, 1H), 8.90 (d, J = 6.7 Hz,1H), 8.70 (s, 1H), 7.99 – 7.90 (m, 2H), 7.80 (d, J = 8.6 Hz, 2H), 7.55 – 7.48(m, 1H), 6.99 (d, J = 8.6 Hz, 2H).

[0040] 3-(imidazo[1,2- α ]Pyridin-2-yl)phenol (LT-2) Following the synthesis of intermediate LT-1, a yellow solid was obtained, yielding 84% at mp 78-79 °C. 1 H NMR (400 MHz, DMSO- d 6) d 9.96 (s, 1H), 8.91 (t, J = 5.8 Hz, 1H), 8.82 (d, J = 7.1 Hz, 1H), 7.96 (d, J = 3.8 Hz, 2H), 7.52 (dt, J = 7.1, 3.8 Hz, 1H), 7.44 – 7.34 (m,2H), 7.31 (s, 1H), 6.96 (d, J = 7.0 Hz, 1H).

[0041] 4-(7-methylimidazo[1,2-) α ]Pyridin-2-yl)phenol (LT-3) Following the synthesis of intermediate LT-1, the product is a white solid with a yield of 94% and an mp of 107-109 °C. 1 H NMR (400MHz, DMSO- d 6) d 10.04 (s, 1H), 8.69 (dd, J= 7.0, 3.2 Hz, 1H), 8.52 – 8.45(m, 1H), 7.78 – 7.75 (m, 2H), 7.64 (s, 1H), 7.26 (d, J = 7.0 Hz, 1H), 6.95(d, J = 8.6 Hz, 2H), 2.52 (s, 3H).

[0042] 3-(7-methylimidazo[1,2-) α ]Pyridin-2-yl)phenol (LT-4) Following the synthesis of intermediate LT-1, the product is a white solid with a yield of 96% and an mp of 106-108 °C. 1 H NMR (400MHz, DMSO- d 6) d 9.94 (s, 1H), 8.85 – 8.76 (m, 1H), 8.76 – 8.67 (m, 1H), 7.74 (s, 1H), 7.45 – 7.33 (m, 3H), 7.30 (t, J = 1.9 Hz, 1H), 6.96 (dt, J = 7.8,1.8 Hz, 1H), 2.57 (s, 3H).

[0043] 4-(6-bromoimidazole[1,2- α ]Pyridin-2-yl)phenol (LT-5) Following the synthesis of intermediate LT-1, the product is a white solid with a yield of 92% and an mp of 168-170 °C. 1 H NMR (400MHz, DMSO- d 6) d 10.16 (s, 1H), 9.24 (s, 1H), 8.53 (d, J = 2.0 Hz, 1H), 8.01(dt, J = 9.5, 1.8 Hz, 1H), 7.87 (d, J = 9.6 Hz, 1H), 7.80 (d, J = 8.7 Hz, 2H), 6.97 (d, J = 8.7 Hz, 2H).

[0044] 3-(6-bromoimidazole[1,2- α ]Pyridin-2-yl)phenol (LT-6) Following the synthesis of intermediate LT-1, the product is a white solid with a yield of 92% and an mp of 142-144 °C. 1 H NMR (400MHz, DMSO- d 6) d 10.16 (s, 1H), 9.24 (s, 1H), 8.53 (d, J = 2.0 Hz, 1H), 8.04 –7.98 (m, 1H), 7.87 (d, J = 9.6 Hz, 1H), 7.80 (d, J = 8.7 Hz, 2H), 6.97 (d, J = 8.7 Hz, 2H).

[0045] 2-(4-(imidazo[1,2-) α 1,2-pyridinyl)phenoxy)methyl acetate (LT-7) Intermediate LT-1 (1.05 g, 5 mmol) was dissolved in 80 mL of DMF, and methyl bromoacetate (0.57 mL, 6 mmol) and Cs₂CO₃ (3.25 g, 10 mmol) were added. The mixture was reacted at 80 °C for 3 h. After the reaction was complete, the mixture was cooled to room temperature, and 250 mL of water was added. The mixture was extracted three times with ethyl acetate. The combined organic phases were washed with saturated NaCl solution and dried over anhydrous Na₂SO₄. The crude product was purified by column chromatography to give a white solid, yield: 65%, mp 117–119 °C. 1 H NMR (400 MHz, DMSO- d 6) d 8.51 (d, J = 6.7 Hz, 1H), 8.30 (s, 1H), 7.89 (d, J = 8.4 Hz, 2H), 7.56 (d, J = 9.1 Hz,1H), 7.31 – 7.18 (m, 1H), 7.01 (d, J = 8.5 Hz, 2H), 6.88 (t, J = 6.7 Hz, 1H), 4.85 (s, 2H), 3.72 (s, 3H).

[0046] 4-(4-(imidazo[1,2-) α Methyl pyridin-2-yl)phenoxy)butyrate (LT-8) Following the synthesis of intermediate LT-7, the product is a white solid with a yield of 63% and an mp of 119-121 °C. 1 H NMR (400 MHz, DMSO- d 6) d 8.50 (d, J = 6.7 Hz, 1H), 8.29 (s, 1H), 7.89 (d, J = 8.7 Hz, 2H), 7.55 (d, J = 9.0 Hz, 1H), 7.27 – 7.18 (m, 1H), 6.99 (d, J = 8.8 Hz, 2H), 6.90– 6.85 (m, 1H), 4.03 (t, J = 6.3 Hz, 2H), 3.62 (s, 3H), 2.50 – 2.45 (m, 2H), 2.00 (p, J = 6.8 Hz, 2H).

[0047] 5-(4-(imidazo[1,2-) α Methyl pyridin-2-yl)phenoxy)valerate (LT-9) Following the synthesis of intermediate LT-7, the product is a white solid with a yield of 50% and an mp of 109-111 °C. 1 H NMR (400 MHz, DMSO- d 6) d 8.50 (d, J = 6.7 Hz, 1H), 8.29 (s, 1H), 7.88 (d, J = 8.7 Hz, 2H), 7.55 (d, J = 9.1 Hz, 1H), 7.27 – 7.15 (m, 1H), 6.99 (d, J = 8.8 Hz, 2H), 6.87(t, J = 6.7 Hz, 1H), 4.01 (t, J = 5.9 Hz, 2H), 3.60 (s, 3H), 2.40 (t, J = 7.0Hz, 2H), 1.72 (td, J = 12.6, 11.5, 6.5 Hz, 4H).

[0048] 6-(4-(imidazo[1,2-) αMethyl pyridin-2-yl)phenoxy)hexanoate (LT-10) Following the synthesis of intermediate LT-7, the product is a white solid with a yield of 54% and an mp of 140-142 °C. 1 H NMR (400 MHz, DMSO- d 6) d 8.50 (d, J = 6.7 Hz, 1H), 8.28 (s, 1H), 7.88 (d, J = 8.6 Hz, 2H), 7.55 (d, J = 9.0 Hz, 1H), 7.30 – 7.17 (m, 1H), 6.99 (d, J = 8.7 Hz, 2H), 6.87(t, J = 6.7 Hz, 1H), 3.99 (t, J = 6.4 Hz, 2H), 3.59 (s, 3H), 2.34 (t, J = 7.4Hz, 2H), 1.73 (p, J = 6.6 Hz, 2H), 1.60 (p, J = 7.4 Hz, 2H), 1.43 (p, J =7.6, 6.9 Hz, 2H).

[0049] 7-(4-(imidazo[1,2-) α Ethyl pyridin-2-yl)phenoxy)heptarate (LT-11) Following the synthesis of intermediate LT-7, a white solid was obtained, yielding 51% at mp 91-93 °C. 1 H NMR (400 MHz, DMSO- d 6) d 8.49 (dd, J = 6.8, 1.3 Hz, 1H), 8.27 (s, 1H), 7.90 – 7.83 (m, 2H),7.54 (d, J = 9.0 Hz, 1H), 7.21 (ddd, J = 8.8, 6.9, 1.3 Hz, 1H), 7.01 – 6.95(m, 2H), 6.86 (td, J = 6.7, 1.2 Hz, 1H), 4.04 (q, J= 7.1 Hz, 2H), 3.98 (t, J = 6.5 Hz, 2H), 2.29 (t, J = 7.3 Hz, 2H), 1.71 (p, J = 6.7 Hz, 2H), 1.55 (p, J = 7.4 Hz, 2H), 1.42 (p, J = 6.7 Hz, 2H), 1.38 – 1.24 (m, 2H), 1.17 (t, J =7.1 Hz, 3H).

[0050] 8-(4-(imidazo[1,2-α]pyridin-2-yl)phenoxy)ethyl octanoate (LT-12) Following the synthesis of intermediate LT-7, a white solid was obtained, with a yield of 56% and an mp of 127-129 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.50 (d, J = 6.7 Hz, 1H), 8.28 (s, 1H), 7.88 (d, J = 8.7 Hz, 2H), 7.55 (d, J = 9.0 Hz, 1H), 7.22 (ddd, J = 9.1, 6.7, 1.3 Hz, 1H), 6.99 (d, J =8.7 Hz, 2H), 6.87 (td, J = 6.8, 1.2 Hz, 1H), 4.05 (q, J = 7.1 Hz, 2H), 3.99(t, J = 6.5 Hz, 2H), 2.28 (t, J = 7.4 Hz, 2H), 1.72 (p, J = 6.7 Hz, 2H), 1.54(p, J = 7.3 Hz, 2H), 1.42 (t, J = 7.7 Hz, 2H), 1.37 – 1.26 (m, 4H), 1.18 (t,J = 7.1 Hz, 3H).

[0051] 2-(3-(imidazo[1,2-α]pyridin-2-yl)phenoxy)methyl acetate (LT-13) Synthesized with reference to intermediate LT-7, yellow solid, yield: 52%, mp 89-91℃. ¹H NMR (400 MHz, DMSO-d6) δ 8.54 – 8.50 (m, 1H), 8.43 (s, 1H), 7.59 (d, J = 8.4 Hz, 2H), 7.53 (d, J = 2.6 Hz, 1H), 7.36 (t, J = 7.9 Hz, 1H), 7.29 – 7.22 (m, 1H), 6.95 – 6.82 (m, 2H), 4.88 (s, 2H), 3.73 (s, 3H).

[0052] 4-(3-(imidazo[1,2-α]pyridin-2-yl)phenoxy)methyl butyrate (LT-14) Following the synthesis of intermediate LT-7, a yellow solid was obtained, yielding 60% at mp 91-93 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.51 (dd, J = 6.8, 1.2 Hz, 1H), 8.42 (s, 1H), 7.65 – 7.46 (m, 3H), 7.34 (t, J = 8.1 Hz, 1H), 7.25 (ddd, J = 9.0, 6.7, 1.2 Hz, 1H), 6.94 – 6.83(m, 2H), 4.07 (t, J = 6.3 Hz, 2H), 3.62 (s, 3H), 2.55 – 2.51 (m, 2H), 2.02(p, J = 6.8 Hz, 2H).

[0053] 5-(3-(imidazo[1,2-α]pyridin-2-yl)phenoxy)methyl valerate (LT-15) Synthesize the intermediate LT-7 as described above. Brown solid, yield: 63%, mp 91-93℃. 1H NMR (400 MHz, DMSO-d6) δ 8.51 (dt, J = 6.8, 1.3 Hz, 1H), 8.42 (s, 1H), 7.64 – 7.49 (m, 3H), 7.34 (t, J = 8.1 Hz, 1H), 7.25 (ddd, J = 9.1, 6.7, 1.3 Hz, 1H), 6.96 – 6.83 (m, 2H), 4.05 (t, J = 5.9 Hz, 2H), 3.60 (s, 3H), 2.41 (t, J = 6.9 Hz, 2H), 1.83 – 1.66 (m, 4H).

[0054] 6-(3-(imidazo[1,2-α]pyridin-2-yl)phenoxy)methyl hexanoate (LT-16) Following the synthesis of intermediate LT-7, a yellow solid was obtained, yielding 60% at mp 90-92°C. 1H NMR (400 MHz, DMSO-d6) δ 8.51 (dt, J = 6.8, 1.2 Hz, 1H), 8.42 (s, 1H), 7.62 – 7.50 (m, 3H), 7.33 (t, J = 8.1 Hz, 1H), 7.25 (ddd, J = 9.0, 6.7, 1.3 Hz, 1H), 6.95 – 6.84(m, 2H), 4.06 – 4.01 (m, 2H), 3.59 (s, 3H), 2.35 (td, J = 7.4, 1.5 Hz, 2H), 1.75 (p, J = 6.8 Hz, 2H), 1.62 (p, J = 7.4 Hz, 2H), 1.52 – 1.39 (m, 2H).

[0055] 7-(3-(imidazo[1,2-α]pyridin-2-yl)phenoxy)ethyl heptanoate (LT-17) Following the synthesis of intermediate LT-7, a yellow solid was obtained, yielding 84% at mp 107-109 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.50 (dd, J = 6.8, 1.3 Hz, 1H), 8.41 (s, 1H), 7.57 (d, J = 9.1 Hz,1H), 7.54 – 7.49 (m, 2H), 7.32 (t, J = 8.1 Hz, 1H), 7.23 (ddd, J = 9.1, 6.8,1.3 Hz, 1H), 6.88 (qd, J = 7.1, 1.8 Hz, 2H), 4.15 – 3.64 (m, 4H), 2.29 (t, J= 7.3 Hz, 2H), 1.73 (p, J = 6.7 Hz, 2H), 1.55 (p, J = 7.4 Hz, 2H), 1.48 –1.39 (m, 2H), 1.38 – 1.29 (m, 2H), 1.16 (t, J = 7.1 Hz, 3H).

[0056] 8-(3-(imidazo[1,2-α]pyridin-2-yl)phenoxy)ethyl octanoate (LT-18) Following the synthesis of intermediate LT-7, a yellow solid was obtained, yielding 49% at mp 113-115 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.51 (dt, J = 6.8, 1.2 Hz, 1H), 8.42 (s, 1H), 7.61 – 7.55 (m, 1H),7.54 – 7.50 (m, 2H), 7.33 (t, J = 8.1 Hz, 1H), 7.24 (ddd, J = 9.1, 6.7, 1.3Hz, 1H), 6.94 – 6.84 (m, 2H), 4.09 – 3.99 (m, 4H), 2.28 (t, J = 7.4 Hz, 2H), 1.74 (p, J = 6.7 Hz, 2H), 1.54 (p, J = 7.3 Hz, 2H), 1.43 (q, J = 7.0 Hz, 2H), 1.34 (tt, J = 10.7, 6.8 Hz, 4H), 1.17 (t, J = 7.1 Hz, 3H).

[0057] 4-((3-(imidazo[1,2-α]pyridin-2-yl)phenoxy)methyl)benzoate (LT-19) Following the synthesis of intermediate LT-7, a brown solid was obtained, with a yield of 72% and an mp of 149-151 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.53 (dt, J = 6.8, 1.2 Hz, 1H), 8.43 (s, 1H), 8.05 – 7.99 (m, 2H), 7.70 – 7.62 (m, 3H), 7.61 – 7.54 (m, 2H), 7.37 (t, J = 7.9 Hz, 1H), 7.26 (ddd, J = 8.8, 6.8, 1.3 Hz, 1H), 6.99 (dd, J = 8.1, 2.6 Hz, 1H), 6.91 (td, J= 6.7, 1.2 Hz, 1H), 5.30 (s, 2H), 3.86 (s, 3H).

[0058] (E)-3-(4-((3-(imidazo[1,2-α]pyridin-2-yl)phenoxy)methyl)phenyl)methyl acrylate (LT-20) Following the synthesis of intermediate LT-7, a brown solid was obtained, yielding 65% at mp 118-120 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.53 (d, J = 6.8 Hz, 1H), 8.33 (s, 1H), 7.90 (d, J = 8.7 Hz, 2H), 7.80 – 7.72 (m, 2H), 7.71 – 7.64 (m, 1H), 7.58 (d, J = 9.1 Hz, 1H), 7.52 (d,J = 7.9 Hz, 2H), 7.28 (t, J = 7.9 Hz, 1H), 7.10 (d, J = 8.5 Hz, 2H), 6.92 (t,J = 6.8 Hz, 1H), 6.67 (d, J = 16.0 Hz, 1H), 5.21 (s, 2H), 3.73 (s, 3H).

[0059] 2-(4-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)methyl acetate (LT-21) Following the synthesis of intermediate LT-7, white solid, yield: 54%, mp 138–140 °C. ¹H NMR (400 MHz, DMSO-d6) δ 8.40–8.36 (m, 1H), 8.19 (s, 1H), 7.86 (d, J = 8.8 Hz, 2H), 7.32 (s, 1H), 6.99 (d, J = 8.8 Hz, 2H), 6.72 (dd, J = 6.9, 1.7 Hz, 1H), 4.84 (s, 2H), 3.72 (s, 3H), 2.35 (s, 3H).

[0060] 4-(4-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)methyl butyrate (LT-22) Following the synthesis of intermediate LT-7, white solid, yield: 55%, mp 128–130 °C. ¹H NMR (400 MHz, DMSO-d6) δ 8.37 (d, J = 6.9 Hz, 1H), 8.17 (s, 1H), 7.91–7.81 (m, 2H), 7.31 (s, 1H), 7.01–6.94 (m, 2H), 6.71 (dd, J = 6.9, 1.7 Hz, 1H), 4.02 (t, J = 6.4 Hz, 2H), 3.62 (s, 3H), 2.50–2.46 (m, 2H), 2.35 (s, 3H), 1.99 (p, J = 6.8 Hz, 2H).

[0061] 5-(4-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)methyl valerate (LT-23) Following the synthesis of intermediate LT-7, white solid, yield: 37%, mp 105–107 °C. ¹H NMR (400 MHz, CDCl₃) δ 7.97 (d, J = 6.9 Hz, 1H), 7.85 (d, J = 8.8 Hz, 2H), 7.68 (s, 1H), 7.36 (s, 1H), 6.94 (d, J = 8.8 Hz, 2H), 6.59 (dd, J = 6.9, 1.6 Hz, 1H), 4.05– 3.99 (m, 2H), 3.68 (s, 3H), 2.47– 2.40 (m, 2H), 2.39 (s, 3H), 1.89– 1.79 (m, 4H).

[0062] 6-(4-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)methyl hexanoate (LT-24) Following the synthesis of intermediate LT-7, a white solid was obtained, yielding 41% at mp 134-136 °C. 1H NMR (400 MHz, CDCl3) δ 7.97 (d, J = 6.9 Hz, 1H), 7.85 (d, J = 8.7 Hz, 2H), 7.68 (s, 1H), 7.36 (s, 1H), 6.94 (d, J = 8.8 Hz, 2H), 6.58 (dd, J = 6.9, 1.6 Hz, 1H), 4.00(t, J = 6.4 Hz, 2H), 3.68 (s, 3H), 2.39 (s, 3H), 2.36 (t, J = 7.4 Hz, 2H),1.87 – 1.78 (m, 2H), 1.72 (p, J = 7.6 Hz, 2H), 1.59 – 1.46 (m, 2H).

[0063] 7-Ethyl-7-(4-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)heptanoate (LT-25) Following the synthesis of intermediate LT-7, a yellow solid was obtained, yielding 82%, with an mp value of 90-92 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.38 (d, J = 6.9 Hz, 1H), 8.31 (s, 1H), 7.54 – 7.47 (m, 2H), 7.37– 7.27 (m, 2H), 6.85 (ddd, J = 8.2, 2.5, 1.1 Hz, 1H), 6.73 (dd, J = 7.0, 1.7Hz, 1H), 4.12 – 3.95 (m, 4H), 2.35 (s, 3H), 2.29 (t, J = 7.3 Hz, 2H), 1.73(p, J = 6.8 Hz, 2H), 1.56 (p, J = 7.4 Hz, 2H), 1.44 (dq, J = 8.8, 6.8 Hz, 2H), 1.39 – 1.30 (m, 2H), 1.17 (t, J = 7.1 Hz, 3H).

[0064] 8-(4-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)ethyl octanoate (LT-26) Following the synthesis of intermediate LT-7, the product is a white solid with a yield of 33% and an mp of 99-101 °C. 1H NMR (400 MHz, CDCl3) δ 7.97 (d, J = 6.9 Hz, 1H), 7.85 (d, J = 8.7 Hz, 2H), 7.68 (s, 1H), 7.37 (s, 1H), 6.95 (d, J = 8.8 Hz, 2H), 6.59 (dd, J = 6.9, 1.6 Hz, 1H), 4.13(q, J = 7.1 Hz, 2H), 3.99 (t, J = 6.5 Hz, 2H), 2.39 (s, 3H), 2.30 (t, J = 7.5Hz, 2H), 1.85 – 1.75 (m, 2H), 1.64 (p, J = 7.4 Hz, 2H), 1.48 (dd, J = 9.5, 5.4 Hz, 2H), 1.43 – 1.32 (m, J = 5.3, 4.7 Hz, 4H), 1.26 (t, J = 7.1 Hz, 3H).

[0065] 2-(3-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)methyl acetate (LT-27) Following the synthesis of intermediate LT-7, white solid, yield: 60%, mp 114–116 °C. ¹H NMR (400 MHz, DMSO-d6) δ 8.40 (d, J = 6.8 Hz, 1H), 8.32 (s, 1H), 7.53 (d, J = 7.7 Hz, 1H), 7.48 (t, J = 1.9 Hz, 1H), 7.39–7.28 (m, 2H), 6.86 (dd, J = 8.1, 2.5 Hz, 1H), 6.75 (dd, J = 6.9, 1.6 Hz, 1H), 4.75 (s, 2H), 2.51 (s, 2H), 2.36 (s, 3H).

[0066] 4-(3-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)methyl butyrate (LT-28) Following the synthesis of intermediate LT-7, a white solid was obtained, yielding 62% at mp 103-105 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.39 (d, J = 6.9 Hz, 1H), 8.31 (s, 1H), 7.53 – 7.47 (m, 2H), 7.37– 7.27 (m, 2H), 6.85 (ddd, J = 8.2, 2.4, 1.2 Hz, 1H), 6.74 (dd, J = 6.9, 1.6Hz, 1H), 4.06 (t, J = 6.3 Hz, 2H), 3.62 (s, 3H), 2.54 – 2.51 (m, 2H), 2.36(s, 3H), 2.02 (q, J = 6.7 Hz, 2H).

[0067] 5-(3-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)methyl valerate (LT-29) Following the synthesis of intermediate LT-7, the product is a white solid with a yield of 59% and an mp of 109-111 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.39 (d, J = 6.9 Hz, 1H), 8.31 (s, 1H), 7.50 (dt, J = 4.0, 1.6 Hz, 2H), 7.39 – 7.27 (m, 2H), 6.86 (dd, J = 8.1, 2.4 Hz, 1H), 6.74 (dd, J = 7.0,1.6 Hz, 1H), 4.04 (t, J = 5.9 Hz, 2H), 3.60 (s, 3H), 2.41 (t, J = 6.9 Hz,2H), 2.36 (s, 3H), 1.75 (pd, J = 8.3, 2.4 Hz, 4H).

[0068] 6-(3-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)methyl hexanoate (LT-30) Following the synthesis of intermediate LT-7, the product is a white solid with a yield of 57% and an mp of 90-92 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.38 (d, J = 7.1 Hz, 1H), 8.31 (s, 1H), 7.54 – 7.46 (m, 2H), 7.37– 7.27 (m, 2H), 6.85 (ddd, J = 8.2, 2.5, 1.0 Hz, 1H), 6.74 (dd, J = 6.9, 1.6Hz, 1H), 4.02 (t, J = 6.4 Hz, 2H), 3.59 (s, 3H), 2.39 – 2.30 (m, 5H), 1.75(p, J = 6.6 Hz, 2H), 1.61 (p, J = 7.4 Hz, 2H), 1.50 – 1.40 (m, 2H).

[0069] 7-Ethyl-7-(3-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)heptanoate (LT-31) Following the synthesis of intermediate LT-7, the product is a white solid with a yield of 46% and an mp of 110-112 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.38 (d, J = 6.9 Hz, 1H), 8.31 (s, 1H), 7.52 – 7.46 (m, 2H), 7.37– 7.27 (m, 2H), 6.85 (ddd, J = 8.2, 2.5, 1.1 Hz, 1H), 6.73 (dd, J = 7.0, 1.7Hz, 1H), 4.11 – 3.96 (m, 4H), 2.35 (s, 3H), 2.29 (t, J = 7.3 Hz, 2H), 1.73(p, J = 6.8 Hz, 2H), 1.56 (p, J = 7.4 Hz, 2H), 1.44 (dq, J = 8.8, 6.8 Hz, 2H), 1.39 – 1.28 (m, 2H), 1.17 (t, J = 7.1 Hz, 3H).

[0070] 8-(3-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)ethyl octanoate (LT-32) Following the synthesis of intermediate LT-7, the product is a white solid with a yield of 53% and an mp of 98-100 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.44 (d, J = 6.9 Hz, 1H), 8.37 (s, 1H), 7.57 – 7.52 (m, 2H), 7.42– 7.34 (m, 2H), 6.91 (ddd, J = 8.2, 2.6, 1.1 Hz, 1H), 6.80 (dd, J = 6.9, 1.6Hz, 1H), 4.09 (p, J = 6.8 Hz, 4H), 2.41 (s, 3H), 2.34 (t, J = 7.4 Hz, 2H), 1.79 (p, J = 6.7 Hz, 2H), 1.60 (p, J = 7.3 Hz, 2H), 1.49 (p, J = 7.1 Hz, 2H), 1.39 (tq, J = 13.5, 7.2 Hz, 4H), 1.23 (t, J = 7.1 Hz, 3H).

[0071] 4-((3-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)methyl)methyl benzoate (LT-33) Following the synthesis of intermediate LT-7, a brown solid was obtained, with a yield of 68% and an mp of 121-123 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.40 (d, J = 7.1 Hz, 1H), 8.31 (s, 1H), 8.06 – 7.97 (m, 2H), 7.70– 7.60 (m, 3H), 7.54 (dt, J = 7.7, 1.2 Hz, 1H), 7.38 – 7.31 (m, 2H), 6.96(ddd, J = 8.3, 2.7, 1.0 Hz, 1H), 6.74 (dd, J = 6.9, 1.7 Hz, 1H), 5.29 (s,2H), 3.86 (s, 3H), 2.35 (d, J = 1.1 Hz, 3H).

[0072] (E)-3-(4-((3-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)methyl)phenyl)methyl acrylate (LT-34) Following the synthesis of intermediate LT-7, a brown solid was obtained, yielding 59% at mp 164-166 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.40 (d, J = 6.9 Hz, 1H), 8.32 (s, 1H), 7.76 (d, J = 8.0 Hz, 2H), 7.68 (d, J = 16.0 Hz, 1H), 7.63 – 7.60 (m, 1H), 7.54 (dd, J = 8.2, 2.5 Hz, 3H), 7.39 – 7.30 (m, 2H), 6.95 (dd, J = 8.2, 2.5 Hz, 1H), 6.74 (dd, J = 6.9,1.6 Hz, 1H), 6.67 (d, J = 16.1 Hz, 1H), 5.23 (s, 2H), 3.73 (s, 3H), 2.35 (s, 3H).

[0073] 2-(4-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)methyl acetate (LT-35) Following the synthesis of intermediate LT-7, white solid, yield: 54%, mp 166-168℃. ¹H NMR (400 MHz, DMSO-d6) δ 8.86 (dd, J = 2.0, 0.9 Hz, 1H), 8.27 (s, 1H), 7.92 – 7.86 (m, 2H), 7.55 (d, J = 9.5 Hz, 1H), 7.34 (dd, J = 9.5, 2.0 Hz, 1H), 7.04 – 6.97 (m, 2H), 4.85 (s, 2H), 3.72 (s, 3H).

[0074] 4-(4-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)methyl butyrate (LT-36) Following the synthesis of intermediate LT-7, a white solid was obtained, with a yield of 47% and an mp of 164-166 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.86 (dd, J = 2.0, 0.9 Hz, 1H), 8.25 (s, 1H), 7.87 (d, J = 8.8 Hz, 2H), 7.54 (dt, J = 9.5, 0.8 Hz, 1H), 7.34 (dd, J = 9.5, 1.9 Hz, 1H), 7.00 (d,J = 8.9 Hz, 2H), 4.03 (t, J = 6.4 Hz, 2H), 3.62 (s, 3H), 2.49 – 2.47 (m, 2H),1.99 (p, J = 6.7 Hz, 2H).

[0075] 5-(4-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)methyl valerate (LT-37) Following the synthesis of intermediate LT-7, a white solid was obtained, yielding 65% at mp 156-158 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.85 (dd, J = 1.9, 0.9 Hz, 1H), 8.25 (s, 1H), 7.87 (d, J = 8.8 Hz, 2H), 7.54 (d, J = 9.5 Hz, 1H), 7.34 (dd, J = 9.5, 1.9 Hz, 1H), 7.00 (d, J =8.8 Hz, 2H), 4.02 (t, J = 6.0 Hz, 2H), 3.59 (s, 3H), 2.40 (t, J = 7.1 Hz,2H), 1.81 – 1.65 (m, 4H).

[0076] 6-(4-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)methyl hexanoate (LT-38) Following the synthesis of intermediate LT-7, the product is a white solid with a yield of 58% and an mp of 154-156 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.85 (dd, J = 1.9, 0.9 Hz, 1H), 8.25 (s, 1H), 7.87 (d, J = 8.7 Hz, 2H), 7.54 (d, J = 9.5 Hz, 1H), 7.34 (dd, J = 9.5, 2.0 Hz, 1H), 6.99 (d, J =8.8 Hz, 2H), 4.00 (t, J = 6.4 Hz, 2H), 3.59 (s, 3H), 2.34 (t, J = 7.4 Hz,2H), 1.73 (p, J = 6.7 Hz, 2H), 1.60 (p, J = 7.4 Hz, 2H), 1.49 – 1.38 (m, 2H).

[0077] Ethyl 7-(4-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)heptanoate (LT-39) Following the synthesis of intermediate LT-7, a white solid was obtained, yielding 68% at mp 136-138 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.85 (dd, J = 2.0, 0.9 Hz, 1H), 8.25 (s, 1H), 7.87 (d, J = 8.8 Hz, 2H), 7.54 (d, J = 9.5 Hz, 1H), 7.33 (dd, J = 9.5, 2.0 Hz, 1H), 6.99 (d, J =8.8 Hz, 2H), 4.05 (q, J = 7.1 Hz, 2H), 4.00 (t, J = 6.5 Hz, 2H), 2.29 (t, J =7.4 Hz, 2H), 1.72 (p, J = 6.7 Hz, 2H), 1.55 (p, J = 7.4 Hz, 2H), 1.43 (dq, J= 13.2, 6.7 Hz, 2H), 1.38 – 1.29 (m, 2H), 1.17 (t, J = 7.1 Hz, 3H).

[0078] 8-(4-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)ethyl octanoate (LT-40) Following the synthesis of intermediate LT-7, the product is a white solid with a yield of 59% and an mp of 135-137 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.85 (s, 1H), 8.25 (s, 1H), 7.87 (d, J = 8.8 Hz, 2H), 7.54 (d, J =9.5 Hz, 1H), 7.33 (dd, J = 9.6, 1.9 Hz, 1H), 6.99 (d, J = 8.4 Hz, 2H), 4.10 –3.97 (m, 4H), 2.28 (t, J = 7.3 Hz, 2H), 1.78 – 1.67 (m, 2H), 1.53 (p, J =7.0, 6.5 Hz, 2H), 1.41 (dd, J = 13.7, 6.8 Hz, 2H), 1.36 – 1.24 (m, 4H), 1.17 (t, J = 7.1 Hz, 3H).

[0079] 2-(3-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)methyl acetate (LT-41) Following the synthesis of intermediate LT-7, white solid, yield: 50%, mp 98-101℃. 1H NMR (400 MHz, DMSO-d6) δ 8.88 (s, 1H), 8.39 (s, 1H), 7.64 – 7.56 (m, 2H), 7.52 (s, 1H), 7.41 – 7.31 (m, 2H), 6.91 (dd, J = 8.2, 2.5 Hz, 1H), 4.89 (s, 2H), 3.72 (s, 3H).

[0080] 4-(3-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)methyl butyrate (LT-42) Following the synthesis of intermediate LT-7, the product is a white solid with a yield of 88% and an mp of 90-92 °C. 1H NMR (400 MHz, CDCl3) δ 8.26 (dd, J = 1.8, 0.9 Hz, 1H), 7.81 (s, 1H), 7.54 (d, J = 9.5 Hz,1H), 7.50 (dd, J = 2.6, 1.5 Hz, 1H), 7.47 (dt, J = 7.6, 1.5 Hz, 1H), 7.33 (t,J = 7.9 Hz, 1H), 7.23 (dd, J = 9.5, 1.9 Hz, 1H), 6.88 (ddd, J = 8.2, 2.6, 1.0Hz, 1H), 4.10 (t, J = 6.1 Hz, 2H), 3.70 (s, 3H), 2.56 (t, J = 7.3 Hz, 2H),2.19 – 2.10 (m, 2H).

[0081] 5-(3-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)methyl valerate (LT-43) Following the synthesis of intermediate LT-7, a yellow solid was obtained, yielding 75% at mp 122-124 °C. 1H NMR (400 MHz, CDCl3) δ 8.26 (dd, J = 1.9, 0.9 Hz, 1H), 7.82 (s, 1H), 7.57 – 7.50 (m, 2H), 7.47 (dt, J = 7.7, 1.2 Hz, 1H), 7.33 (t, J = 7.9 Hz, 1H), 7.23 (dd, J = 9.5,1.9 Hz, 1H), 6.88 (ddd, J = 8.2, 2.6, 1.0 Hz, 1H), 4.13 – 4.05 (m, 2H), 3.68(s, 3H), 2.42 (td, J = 6.8, 5.4, 3.1 Hz, 2H), 1.92 – 1.82 (m, 4H).

[0082] 6-(3-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)methyl hexanoate (LT-44) Following the synthesis of intermediate LT-7, a yellow solid was obtained, yielding 78% at mp 99-101 °C. 1H NMR (400 MHz, CDCl3) δ 8.27 (dd, J = 1.9, 0.9 Hz, 1H), 7.82 (s, 1H), 7.56 – 7.50 (m, 2H), 7.47 (dt, J = 7.6, 1.2 Hz, 1H), 7.33 (t, J = 7.9 Hz, 1H), 7.23 (dd, J = 9.5,1.9 Hz, 1H), 6.92 – 6.85 (m, 1H), 4.06 (t, J = 6.4 Hz, 2H), 3.68 (s, 3H),2.36 (t, J = 7.5 Hz, 2H), 1.83 (dt, J = 14.2, 6.7 Hz, 2H), 1.77 – 1.68 (m, 2H), 1.59 – 1.48 (m, 2H).

[0083] 7-(3-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)ethyl heptanoate (LT-45) Following the synthesis of intermediate LT-7, a yellow solid was obtained in 73% yield, with mp values ​​of 114–116 °C. ¹H NMR (400 MHz, CDCl₃) showed the following values: δ 8.26 (dd, J = 2.0, 0.9 Hz, 1H), 7.82 (s, 1H), 7.56–7.50 (m, 2H), 7.47 (dt, J = 7.6, 1.2 Hz, 1H), 7.33 (t, J = 7.9 Hz, 1H), 7.23 (dd, J = 9.5, 1.9 Hz, 1H), 6.89 (ddd, J = 8.2, 2.6, 1.0 Hz, 1H), 4.13 (q, J = 7.1 Hz, 2H), 4.05 (t, J = 6.5 Hz, 2H). 2H), 2.32 (t, J = 7.5 Hz, 2H), 1.87 – 1.77 (m, 2H), 1.67(p, J = 7.5 Hz, 2H), 1.51 (dq, J = 9.6, 7.1 Hz, 2H), 1.45 – 1.36 (m, 2H),1.26 (t, J = 7.1 Hz, 3H).

[0084] 8-(3-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)ethyl octanoate (LT-46) Following the synthesis of intermediate LT-7, a yellow solid was obtained, yielding 89% at mp 104-106 °C. 1H NMR (400 MHz, CDCl3) δ 8.27 – 8.23 ​​(m, 1H), 7.85 (d, J = 8.7 Hz, 2H), 7.74 (s, 1H), 7.50 (d, J = 9.5 Hz, 1H), 7.21 (dd, J = 9.5, 1.9 Hz, 1H), 6.96 (d, J = 8.8 Hz,2H), 4.13 (q, J = 7.1 Hz, 2H), 4.00 (t, J = 6.5 Hz, 2H), 2.30 (t, J = 7.5 Hz,2H), 1.86 – 1.76 (m, 2H), 1.65 (p, J = 7.3 Hz, 2H), 1.47 (q, J = 7.2 Hz, 2H), 1.37 (dq, J = 7.7, 4.2 Hz, 4H), 1.26 (t, J = 7.2 Hz, 3H).

[0085] 4-((3-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)methyl)benzoate (LT-47) Synthesized with reference to intermediate LT-7, brown solid, yield: 59%, mp 149–151 °C. ¹H NMR (400 MHz, DMSO-d⁶) δ 8.88 (d, J = 2.2 Hz, 1H), 8.38 (s, 1H), 8.01 (d, J = 8.3 Hz, 2H), 7.67–7.62 (m, 3H), 7.60–7.53 (m, 2H), 7.41–7.32 (m, 2H), 7.00 (dd, J = 8.2, 2.6 Hz, 1H), 5.30 (s, 2H), 3.86 (s, 3H).

[0086] (E)-3-(4-((3-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)methyl)phenyl)methyl acrylate (LT-48) Following the synthesis of intermediate LT-7, a brown solid was obtained, yielding 43% at mp 156-158 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.88 (d, J = 1.9 Hz, 1H), 8.38 (s, 1H), 7.76 (d, J = 8.1 Hz, 2H), 7.68 (d, J = 16.0 Hz, 1H), 7.63 (t, J = 1.9 Hz, 1H), 7.60 – 7.51 (m, 4H), 7.40 – 7.33 (m, 2H), 6.99 (dd, J = 8.1, 2.5 Hz, 1H), 6.66 (d, J = 16.1 Hz, 1H), 5.23 (s, 2H), 3.73 (s, 3H).

[0087] Example 2. N-hydroxy-2-(4-(imidazo[1,2-α]pyridin-2-yl)phenoxy)acetamide (HDDI-1) Hydroxylamine hydrochloride (4.67 g, 67 mmol) was dissolved in 24 mL of methanol, and potassium hydroxide (5.60 g, 100 mmol) was dissolved in 14 mL of methanol. The methanol solution of potassium hydroxide was slowly added dropwise to hydroxylamine hydrochloride under ice bath conditions. The reaction was carried out under ice bath conditions for 30 min, and then filtered to obtain a freshly prepared methanol solution of hydroxylamine / potassium hydroxide.

[0088] Intermediate LT-7 (2 mmol, 0.56 g) was dissolved in 24 mL of freshly prepared hydroxylamine / potassium hydroxide methanol solution and reacted with stirring at room temperature for 3 h. Some methanol was removed by vacuum distillation, and the pH was adjusted to 7 by slow dropwise addition of 1 M HCl solution under ice bath conditions. A solid precipitated, which was filtered. The crude product was purified by column chromatography to give a yellow solid, yield 57%, mp 186-188℃. 1H NMR (400 MHz, DMSO-d6) δ 10.90 (s, 1H), 9.05 (s, 1H), 8.51 (d, J = 6.7 Hz, 1H), 8.31 (s,1H), 7.90 (d, J = 8.6 Hz, 2H), 7.56 (d, J = 9.0 Hz, 1H), 7.23 (t, J = 7.8 Hz,1H), 7.04 (d, J = 8.7 Hz, 2H), 6.88 (t, J = 6.5 Hz, 1H), 4.52 (s, 2H). 13CNMR (100 MHz, DMSO-d6), δ 164.28, 157.55, 144.73, 144.25, 127.17, 126.80,126.73, 124.72, 116.41, 114.91, 112.11, 108.19, 65.92. HRMS (AP-ESI) m / z,calcd for C15H13N3O3, ([M+H]+): 284.1035, found: 284.1039.

[0089] Example 3. N-hydroxy-4-(4-(imidazo[1,2-α]pyridin-2-yl)phenoxy)butyramide (HDDI-2) Following the synthesis of the target compound HDDI-1, a yellow solid was obtained in 82% yield at mp 186-188 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.47 (s, 1H), 8.78 (s, 1H), 8.50 (d, J = 6.7 Hz, 1H), 8.29 (s, 1H), 7.89 (d, J = 8.7 Hz, 2H), 7.55 (d, J = 9.0 Hz, 1H), 7.27 – 7.19(m, 1H), 7.00 (d, J = 8.7 Hz, 2H), 6.88 (t, J = 6.7 Hz, 1H), 4.00 (t, J = 6.3Hz, 2H), 2.16 (t, J = 7.3 Hz, 2H), 1.96 (p, J = 6.6 Hz, 2H). 13C NMR (100MHz, DMSO-d6), δ 168.64, 158.31, 144.71, 144.41, 126.87, 126.69, 126.50,124.65, 116.37, 114.67, 112.06, 108.02, 66.85, 28.76, 24.85. HRMS (AP-ESI) m / z, calcd for C17H17N3O3, ([M+H]+): 312.1348, found: 312.1349.

[0090] Example 4. N-hydroxy-5-(4-(imidazo[1,2-α]pyridin-2-yl)phenoxy)pentanamide (HDDI-3) The target compound HDDI-1 was synthesized as a white solid, yield: 75%, mp 199-201℃. 1H NMR (400 MHz, DMSO-d6) δ 10.42 (s, 1H), 8.76 (s, 1H), 8.50 (d, J = 6.7 Hz, 1H), 8.29 (s, 1H), 7.88 (d, J = 8.8 Hz, 2H), 7.55 (d, J = 9.0 Hz, 1H), 7.28 – 7.18(m, 1H), 7.00 (d, J = 8.8 Hz, 2H), 6.88 (td, J = 6.8, 1.0 Hz, 1H), 4.01 (t, J= 5.9 Hz, 2H), 2.04 (t, J = 6.9 Hz, 2H), 1.81 – 1.60 (m, 4H). 13C NMR (100MHz, DMSO-d6), δ 168.94, 158.41, 144.73, 144.46, 126.87, 126.69, 126.43,124.64, 116.39, 114.65, 112.06, 108.01, 67.10, 31.93, 28.21, 21.82. HRMS (AP-ESI) m / z, calcd for C18H19N3O3, ([M+H]+): 326.1505, found: 326.1509.

[0091] Example 5. N-hydroxy-6-(4-(imidazo[1,2-α]pyridin-2-yl)phenoxy)hexanoamide (HDDI-4) Following the synthesis of the target compound HDDI-1, a pale yellow solid was obtained in 48% yield at mp 194-196 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.38 (s, 1H), 8.71 (s, 1H), 8.50 (d, J = 6.7 Hz, 1H), 8.28 (s, 1H), 7.88 (d, J = 8.7 Hz, 2H), 7.55 (d, J = 9.0 Hz, 1H), 7.25 – 7.18(m, 1H), 6.99 (d, J = 8.8 Hz, 2H), 6.87 (t, J = 7.2 Hz, 1H), 3.99 (t, J = 6.4Hz, 2H), 1.99 (t, J = 7.3 Hz, 2H), 1.78 – 1.67 (m, 2H), 1.62 – 1.51 (m, 2H),1.48 – 1.36 (m, 2H). 13C NMR (100 MHz, DMSO-d6), δ 169.04, 158.45, 144.73,144.47, 126.87, 126.70, 126.41, 124.63, 116.39, 114.62, 112.05, 108.00,67.37, 32.25, 28.46, 25.20, 24.93. HRMS (AP-ESI) m / z, calcd for C19H21N3O3,([M+H]+): 340.1661, found: 340.1666.

[0092] Example 6. N-hydroxy-7-(4-(imidazo[1,2-α]pyridin-2-yl)phenoxy)heptamide (HDDI-5) The target compound HDDI-1 was synthesized as a white solid, yield: 60%, mp 176-178℃. 1H NMR (400 MHz, DMSO-d6) δ 10.36 (s, 1H), 8.69 (s, 1H), 8.50 (d, J = 6.6 Hz, 1H), 8.28 (s, 1H), 7.88 (d, J = 8.3 Hz, 2H), 7.55 (d, J = 9.0 Hz, 1H), 7.29 – 7.15(m, 1H), 6.99 (d, J = 8.4 Hz, 2H), 6.87 (t, J = 6.7 Hz, 1H), 3.99 (t, J = 6.3Hz, 2H), 1.97 (t, J = 7.2 Hz, 2H), 1.72 (p, J = 6.5 Hz, 2H), 1.53 (p, J = 7.3Hz, 2H), 1.42 (dt, J = 14.6, 7.5 Hz, 2H), 1.31 (dt, J = 14.0, 7.6 Hz, 2H).13C NMR (100 MHz, DMSO-d6), δ 169.10, 158.45, 144.71, 144.47, 126.86, 126.68,126.39, 124.61, 116.38, 114.62, 112.03, 107.98, 67.41, 32.23, 28.61, 28.36,25.27, 25.09. HRMS (AP-ESI) m / z, calcd for C20H23N3O3, ([M+H]+): 354.1818, found: 354.1816.

[0093] Example 7. N-hydroxy-8-(4-(imidazo[1,2-α]pyridin-2-yl)phenoxy)octamide (HDDI-6) Following the synthesis of the target compound HDDI-1, a white solid was produced in 66% yield at mp 184-186 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.36 (s, 1H), 8.70 (s, 1H), 8.50 (d, J = 6.7 Hz, 1H), 8.28 (s, 1H), 7.88 (d, J = 8.6 Hz, 2H), 7.55 (d, J = 9.0 Hz, 1H), 7.29 – 7.16(m, 1H), 6.99 (d, J = 8.7 Hz, 2H), 6.87 (t, J = 6.7 Hz, 1H), 3.99 (t, J = 6.5Hz, 2H), 1.95 (t, J = 7.3 Hz, 2H), 1.72 (p, J = 6.5 Hz, 2H), 1.51 (p, J = 7.3Hz, 2H), 1.45 – 1.37 (m, 2H), 1.36 – 1.21 (m, 4H). 13C NMR (100 MHz, DMSO-d6), δ 169.16, 158.48, 144.72, 144.45, HRMS (AP-ESI) m / z, calcd for C21H25N3O3, ([M+H]+): 368.1974, found:368.1978.

[0094] Example 8. N-hydroxy-2-(3-(imidazo[1,2-α]pyridin-2-yl)phenoxy)acetamide (HDDI-7) Following the synthesis of the target compound HDDI-1, a pale yellow solid was obtained, yielding 48% at mp 180-182 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.95 (s, 1H), 9.05 (s, 1H), 8.60 (d, J = 6.7 Hz, 1H), 8.49 (s, 1H), 7.65 (d, J = 9.0 Hz, 1H), 7.62 – 7.54 (m, 2H), 7.39 (t, J = 7.9Hz, 2H), 7.00 (t, J = 6.7 Hz, 1H), 6.96 (dd, J = 8.2, 1.9 Hz, 1H), 4.57 (s,2H). 13C NMR (100 MHz, DMSO-d6), δ 164.31, 158.29, 144.00, 142.64, 134.12,129.93, 127.29, 126.42, 118.68, 115.91, 114.61, 113.16, 111.72, 109.80,65.88. HRMS (AP-ESI) m / z, calcd for C15H13N3O3, ([M+H]+): 284.1035, found:284.1039.

[0095] Example 9. N-hydroxy-4-(3-(imidazo[1,2-α]pyridin-2-yl)phenoxy)butyramide (HDDI-8) Following the synthesis of the target compound HDDI-1, a pale yellow solid was obtained in 77% yield at mp 162-164 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.47 (s, 1H), 8.77 (s, 1H), 8.51 (d, J = 6.7 Hz, 1H), 8.42 (s, 1H), 7.59 (d, J = 9.1 Hz, 1H), 7.55 – 7.51 (m, 2H), 7.34 (t, J = 8.0Hz, 1H), 7.27 – 7.22 (m, 1H), 6.94 – 6.85 (m, 2H), 4.04 (t, J = 6.3 Hz, 2H), 2.18 (t, J = 7.3 Hz, 2H), 1.98 (p, J = 6.6 Hz, 2H). 13C NMR (100 MHz, DMSO-d6), δ 168.69, 158.95, 144.73, 144.22, 135.33, 129.80, 126.87, 124.98,117.96, 116.66, 114.12, 112.32, 111.20, 109.41, 66.78, 28.77, 24.90. HRMS(AP-ESI) m / z, calcd for C17H17N3O3, ([M+H]+): 312.1348, found: 312.1349.

[0096] Example 10. N-hydroxy-5-(3-(imidazo[1,2-α]pyridin-2-yl)phenoxy)pentanamide (HDDI-9) Following the synthesis of the target compound HDDI-1, a pale yellow solid was obtained in 76% yield. 1H NMR (400 MHz, DMSO-d6) δ 10.42 (s, 1H), 8.74 (s, 1H), 8.51 (d, J = 6.1 Hz, 1H), 8.43 (s,1H), 7.58 (d, J = 9.2 Hz, 1H), 7.53 (d, J = 7.0 Hz, 1H), 7.34 (t, J = 7.5 Hz,1H), 7.29 – 7.20 (m, 1H), 6.90 (t, J = 8.0 Hz, 1H), 4.04 (t, J = 5.8 Hz, 2H), 2.05 (t, J = 5.9 Hz, 2H), 1.81 – 1.61 (m, 4H). 13C NMR (100 MHz, DMSO-d6), δ168.93, 159.00, 144.71, 144.23, 135.31, 129.76, 126.84, 124.94, 117.88,116.64, 114.10, 112.30, 111.16, 109.40, 67.01, 31.93, 28.23, 21.81. HRMS (AP-ESI) m / z, calcd for C18H19N3O3, ([M+H]+): 326.1505, found: 326.1508.

[0097] Example 11. N-hydroxy-6-(3-(imidazo[1,2-α]pyridin-2-yl)phenoxy)hexanoamide (HDDI-10) Following the synthesis of the target compound HDDI-1, a white solid was obtained, yielding 65% at mp 154-156 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.39 (s, 1H), 8.72 (s, 1H), 8.51 (d, J = 6.7 Hz, 1H), 8.43 (s, 1H), 7.59 (d, J = 9.1 Hz, 1H), 7.53 (d, J = 7.1 1.75 (p, J = 6.5 Hz, 2H), 1.58 (p, J = 7.3 Hz, 2H), 1.43 (p, J = 7.5, 7.0 Hz, 2H). 13C NMR (100 MHz, DMSO-d6), δ 169.06,159.05, 144.70, 144.21, 135.28, 129.79, 126.87, 124.99, 117.86, 116.64,114.06, 112.33, 111.17, 109.42, 67.31, 32.27, 28.50, 25.22, 24.94. HRMS (AP-ESI) m / z, calcd for C19H21N3O3, ([M+H]+): 340.1661, found: 340.1665.

[0098] Example 12. N-hydroxy-7-(3-(imidazo[1,2-α]pyridin-2-yl)phenoxy)heptamide (HDDI-11) The target compound HDDI-1 was synthesized as a yellow solid, yield: 68%, mp 137-139℃. 1H NMR (400 MHz, DMSO-d6) δ 10.37 (s, 1H), 8.70 (s, 1H), 8.51 (d, J = 6.7 Hz, 1H), 8.43 (s, 1H), 7.58 (d, J = 9.0 Hz, 1H), 7.53 (d, J = 7.5 Hz, 2H), 7.33 (t, J= 8.1 Hz, 1H), 7.29 – 7.18 (m, 1H), 6.89 (q, J = 7.1 Hz, 2H), 4.03 (t, J =6.4 Hz, 2H), 1.97 (t, J = 7.3 Hz, 2H), 1.81 – 1.68 (m, 2H), 1.59 – 1.49 (m,2H), 1.48 – 1.39 (m, 2H), 1.38 – 1.27 (m, 2H). 13C NMR (100 MHz, DMSO-d6), δ169.02, 159.00, 145.11, 143.97, 135.48, HRMS (AP-ESI) m / z, calcd for C20H23N3O3, ([M+H]+): 354.1818, found:354.1816.

[0099] Example 13. N -hydroxy-8-(3-(imidazo[1,2-) α ]Pyridin-2-yl)phenoxy)octamide (HDDI-12) The target compound HDDI-1 was synthesized as a yellow solid, yield: 39%, mp 143-145 ℃. 1 H NMR (400 MHz, DMSO-) d 6) d 10.36 (s, 1H), 8.69 (s, 1H), 8.51 (d, J = 6.7 Hz, 1H),8.42 (s, 1H), 7.58 (d, J= 9.1 Hz, 1H), 7.55 – 7.49 (m, 2H), 7.33 (t, J = 8.1Hz, 1H), 7.29 – 7.21 (m, 1H), 6.94 – 6.83 (m, 2H), 4.03 (t, J = 6.5 Hz, 2H), 1.96 (t, J = 7.3 Hz, 2H), 1.74 (p, J = 6.6 Hz, 2H), 1.51 (p, J = 7.5 Hz, 2H), 1.42 (q, J = 7.2 Hz, 2H), 1.31 (dp, J = 19.7, 6.5 Hz, 4H). 13 C NMR (100 MHz, DMSO- d 6) d 169.14, 159.08, 144.73, 144.26, 135.32, 129.78, 126.86, 124.95,117.85, 116.66, 114.07, 112.31, 111.18, 109.41, 67.39, 32.27, 28.73, 28.56,28.52, 25.46, 25.09. HRMS (AP-ESI) m / z, calcd for C 21 H 25 N3O3, ([M+H) + ):368.1974, found: 368.1978.

[0100] Example 14. N -hydroxy-4-((3-(imidazo[1,2-) α ]Pyridin-2-yl)phenoxy)methyl)benzamide (HDDI-13) The target compound HDDI-1 was synthesized as a white solid, yield: 74%, mp 122-124℃. 1 H NMR (400MHz, DMSO- d 6) d 11.23 (s, 1H), 9.05 (s, 1H), 8.51 (s, 1H), 8.42 (s, 1H), 7.79(d, J= 8.0 Hz, 2H), 7.67 – 7.63 (m, 1H), 7.60 – 7.54 (m, 4H), 7.36 (t, J =7.9 Hz, 1H), 7.25 (ddd, J = 8.8, 6.8, 1.3 Hz, 1H), 6.98 (dd, J = 8.1, 2.7 Hz, 1H), 6.90 (td, J = 6.7, 1.2 Hz, 1H), 5.25 (s, 2H). 13 C NMR (101 MHz, DMSO) d 164.00, 158.58, 144.69, 144.06, 140.35, 135.38, 132.21, 129.86, 127.34,127.05, 126.90, 125.05, 118.32, 116.62, 114.35, 112.36, 111.65, 109.46,68.61, 40.15, 39.94, 39.73, 39.52, 39.31, 39.10, 38.89. HRMS (AP-ESI) m / z,calcd for C 21 H 17 N3O3, ([M+H) + ): 360.1348, found: 360.1351.

[0101] Example 15. (E) - N -hydroxy-3-[4-[[3-(imidazo[1,2-] α [Pyridin-2-yl)phenoxy]methyl]phenyl]acrylamide (HDDI-14) The target compound HDDI-1 was synthesized as a white solid in 81% mp. 230-232℃. 1 H NMR (400MHz, DMSO- d 6) d 10.79 (s, 1H), 9.07 (s, 1H), 8.52 (d, J = 6.7 Hz, 1H), 8.42(s, 1H), 7.65 (d, J = 2.5 Hz, 1H), 7.63 – 7.43 (m, 7H), 7.36 (t,J = 7.9 Hz, 1H), 7.25 (dd, J = 9.1, 6.6 Hz, 1H), 6.97 (dd, J = 8.2, 2.6 Hz, 1H), 6.90 (t, J = 6.7 Hz, 1H), 6.49 (d, J = 15.8 Hz, 1H), 5.22 (s, 2H). 13 C NMR (101 MHz, DMSO) d 162.72, 158.65, 144.74, 144.15, 138.56, 138.00, 135.42, 134.33,129.86, 128.10, 127.62, 126.90, 125.01, 119.16, 118.29, 116.67, 114.36,112.34, 111.65, 109.46, 68.78. HRMS (AP-ESI) m / z, calcd for C 23 H 19 N3O3, ([M+H) + ): 386.1505, found: 386.1509.

[0102] Example 16. N -hydroxy-2-(4-(7-methylimidazo[1,2-] α ]Pyridin-2-yl)phenoxy)acetamide (HDDI-15) Following the synthesis of the target compound HDDI-1, a pale yellow solid was obtained in 57% yield, mp... 189-191℃. 1 H NMR (400 MHz, DMSO-) d 6) d 10.86 (s, 1H), 9.00 (s, 1H), 8.38 (d, J = 6.9 Hz, 1H),8.19 (s, 1H), 7.86 (d, J = 8.4 Hz, 2H), 7.32 (s, 1H), 7.01 (d, J = 8.5 Hz, 2H), 6.72 (d, J = 6.9 Hz, 1H), 4.50 (s, 2H), 2.35 (s, 3H). 13C NMR (100 MHz, DMSO- d 6) d HRMS (AP-ESI) m / z, calcd forC 16 H 15 N3O3, ([M+H) + ): 298.1192, found: 298.1193.

[0103] Example 17. N -hydroxy-4-(4-(7-methylimidazo[1,2-) α ]Pyridin-2-yl)phenoxy)butyramide (HDDI-16) The target compound HDDI-1 was synthesized as a pale yellow solid in 84% yield, mp... 221-223℃. 1 H NMR (400 MHz, DMSO-) d 6) d 10.43 (s, 1H), 8.72 (s, 1H), 8.38 (d, J = 6.9 Hz, 1H),8.18 (s, 1H), 7.85 (d, J = 8.7 Hz, 2H), 7.31 (s, 1H), 6.98 (d, J = 8.7 Hz,2H), 6.77 – 6.66 (m, 1H), 3.99 (t, J = 6.3 Hz, 2H), 2.35 (s, 3H), 2.15 (t, J = 7.4 Hz, 2H), 1.95 (p, J = 6.8 Hz, 2H). 13 C NMR (100 MHz, DMSO- d 6) d168.62,158.17, 145.11, 144.14, 135.01, 126.75, 126.68, 125.90, 114.69, 114.61,114.47, 107.36, 66.83, 28.75, 24.85, 20.83. HRMS (AP-ESI) m / z, calcd forC 18 H 19 N3O3, ([M+H) + ): 326.1505, found: 326.1509.

[0104] Example 18. N -hydroxy-5-(4-(7-methylimidazo[1,2-) α ]Pyridin-2-yl)phenoxy)pentanamide (HDDI-17) The target compound HDDI-1 was synthesized as a pale yellow solid in 81% yield, mp... 191-193℃. 1 H NMR (400 MHz, DMSO-) d 6) d 10.41 (s, 1H), 8.74 (s, 1H), 8.38 (d, J = 6.9 Hz, 1H),8.18 (s, 1H), 7.85 (d, J = 8.7 Hz, 2H), 7.32 (s, 1H), 6.98 (d, J = 8.8 Hz, 2H), 6.72 (dd, J = 6.9, 1.3 Hz, 1H), 4.00 (t, J = 5.9 Hz, 2H), 2.35 (s, 3H), 2.04 (t, J = 6.9 Hz, 2H), 1.81 – 1.57 (m, 4H). 13 C NMR (100 MHz, DMSO- d 6) d 168.93, 158.30, 145.04, 144.03, 135.17, 126.77, 126.47, 125.92, 114.60,114.55, 107.38, 67.08, 31.92, 28.20, 21.80, 20.83. HRMS (AP-ESI) m / z, calcdfor C19 H 21 N3O3, ([M+H) + ): 340.1661, found: 340.1664.

[0105] Example 19. N -hydroxy-6-(4-(7-methylimidazo[1,2-] α ]Pyridin-2-yl)phenoxy)hexamamide (HDDI-18) The target compound HDDI-1 was synthesized as a white solid in 49% mp. 200-202℃. 1 H NMR (400MHz, DMSO- d 6) d 10.38 (s, 1H), 8.72 (s, 1H), 8.37 (d, J = 6.9 Hz, 1H), 8.17(s, 1H), 7.85 (d, J = 8.7 Hz, 2H), 7.31 (s, 1H), 6.97 (d, J = 8.7 Hz, 2H), 6.71 (d, J = 6.8 Hz, 1H), 3.98 (t, J = 6.4 Hz, 2H), 2.35 (s, 3H), 1.99 (t, J = 7.3 Hz, 2H), 1.72 (p, J = 6.6 Hz, 2H), 1.56 (q, J = 7.4 Hz, 2H), 1.40 (p, J = 7.4, 6.7 Hz, 2H). 13 C NMR (100 MHz, DMSO- d 6) d 169.01, 158.29, 145.12,144.20, 134.97, 126.75, 126.58, 125.88, 114.69, 114.55, 114.45, 107.32,67.35, 32.24, 28.46, 25.20, 24.92, 20.82. HRMS (AP-ESI) m / z, calcd forC 20 H 23 N3O3, ([M+H) +): 354.1818, found: 354.1822.

[0106] Example 20. N -hydroxy-7-(4-(7-methylimidazo[1,2-] α ]Pyridin-2-yl)phenoxy)heptanamide (HDDI-19) The target compound HDDI-1 was synthesized as a white solid in 57% mp. 201-203℃. 1 H NMR (400MHz, DMSO- d 6) d 10.37 (s, 1H), 8.71 (s, 1H), 8.37 (d, J = 6.8 Hz, 1H), 8.17(s, 1H), 7.85 (d, J = 8.6 Hz, 2H), 7.32 (s, 1H), 6.97 (d, J = 8.6 Hz, 2H), 6.71 (d, J = 6.8 Hz, 1H), 3.98 (t, J = 6.3 Hz, 2H), 2.35 (s, 3H), 1.97 (t, J = 7.3 Hz, 2H), 1.71 (p, J = 6.3 Hz, 2H), 1.52 (p, J = 7.3 Hz, 2H), 1.45 –1.37 (m, 2H), 1.31 (q, J = 13.0, 10.2 Hz, 2H). 13 C NMR (100 MHz, DMSO- d 6) d 169.09, 158.31, 145.12, 144.20, 134.97, 126.75, 126.57, 125.88, 114.70,114.56, 114.45, 107.32, 67.39, 32.22, 28.61, 28.36, 25.27, 25.09, 20.83. HRMS(AP-ESI) m / z, calcd for C 21 H 25 N3O3, ([M+H) +): 368.1974, found: 368.1971.

[0107] Example 21. N-hydroxy-8-(4-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)octamide (HDDI-20) The target compound HDDI-1 was synthesized as a yellow solid, yield: 90%, mp 188-190℃. 1H NMR(400 MHz, DMSO-d6) δ 10.34 (s, 1H), 8.67 (s, 1H), 8.37 (d, J = 6.9 Hz, 1H), 8.17 (s, 1H), 7.84 (d, J = 8.5 Hz, 2H), 7.31 (s, 1H), 6.97 (d, J = 8.6 Hz, 2H), 6.71 (d, J = 6.8 Hz, 1H), 3.99 (t, J = 6.5 Hz, 2H), 2.35 (s, 3H), 1.95(t, J = 7.3 Hz, 2H), 1.77 – 1.65 (m, 2H), 1.57 – 1.46 (m, 2H), 1.41 (dt, J =14.5, 6.8 Hz, 2H), 1.36 – 1.20 (m, 4H). 13C NMR (100 MHz, DMSO-d6), δ 169.11,158.33, 145.11, 144.18, 135.01, 126.76, HRMS(AP-ESI) m / z, calcd for C22H27N3O3, ([M+H]+): 382.2131, found: 382.2134.

[0108] Example 22. N-hydroxy-2-(3-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)acetamide (HDDI-21) Following the synthesis of the target compound HDDI-1, a pale yellow solid was obtained, yielding 69%, with an mp value of 190-192 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.92 (s, 1H), 9.02 (s, 1H), 8.41 (d, J = 6.9 Hz, 1H), 8.31 (s, 1H), 7.54 (d, J = 8.1 Hz, 2H), 7.38 – 7.30 (m, 2H), 6.94 – 6.86 (m,1H), 6.75 (dd, J = 6.9, 1.3 Hz, 1H), 4.55 (s, 2H), 2.36 (s, 3H). 13C NMR (101MHz, DMSO) δ 164.36, 158.22, 145.14, 143.79, 135.50, 135.35, 129.73, 126.12,118.52, 114.88, 114.83, 113.96, 111.56, 108.85, 65.87, 20.87. HRMS (AP-ESI)m / z, calcd for C16H15N3O3, ([M+H]+): 298.1192, found: 298.1194.

[0109] Example 23. N-hydroxy-4-(3-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)butyramide (HDDI-22) The target compound HDDI-1 was synthesized as a white solid, yield: 60%, mp 181-183℃. 1H NMR (400 MHz, DMSO-d6) δ 10.47 (s, 1H), 8.77 (s, 1H), 8.39 (d, J = 6.8 Hz, 1H), 8.31 (s, 1H), 7.50 (d, J = 7.1 Hz, 2H), 7.39 – 7.27 (m, 2H), 6.86 (d, J = 7.2Hz, 1H), 6.74 (d, J = 6.6 Hz, 1H), 4.03 (t, J = 6.1 Hz, 2H), 2.35 (s, 3H), 2.18 (t, J = 7.2 Hz, 2H), 1.98 (p, J = 6.4 Hz, 2H). 13C NMR (100 MHz, DMSO-d6), δ 168.67, 158.90, 145.12, 143.94, 135.49, 135.35, 129.72, 126.03,117.86, 114.89, 114.76, 113.90, 111.12, 108.76, 66.75, 28.77, 24.90, 20.86.HRMS (AP-ESI) m / z, calcd for C18H19N3O3, ([M+H]+): 326.1505, found: 326.1495.

[0110] Example 24. N-hydroxy-5-(3-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)pentanamide (HDDI-23) Following the synthesis of the target compound HDDI-1, a yellow solid was obtained in 59% yield at mp 160-162 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.42 (s, 1H), 8.75 (s, 1H), 8.39 (d, J = 6.9 Hz, 1H), 8.32 (s, 1H), 7.50 (d, J = 7.5 Hz, 2H), 7.38 – 7.27 (m, 2H), 6.92 – 6.82 (m,1H), 6.74 (d, J = 6.9 Hz, 1H), 4.04 (t, J = 5.6 Hz, 2H), 2.36 (s, 3H), 2.05(t, J = 6.7 Hz, 2H), 1.83 – 1.59 (m, 4H). 13C NMR (100 MHz, DMSO-d6), δ168.92, 158.98, 145.12, 143.98, 135.48, 135.34, 129.70, 126.03, 117.79,114.89, 114.75, 113.91, 111.08, 108.77, 66.99, 31.92, 28.23, 21.82, 20.86.HRMS (AP-ESI) m / z, calcd for C19H21N3O3, ([M+H]+): 340.1661, found: 340.1652.

[0111] Example 25. N-hydroxy-6-(3-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)hexanoamide (HDDI-24) Following the synthesis of the target compound HDDI-1, a pink solid was produced in 58% yield at mp 181-183 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.38 (s, 1H), 8.72 (s, 1H), 8.39 (d, J = 6.9 Hz, 1H), 8.32 (s, 1H), 7.50 (d, J = 6.3 Hz, 2H), 7.37 – 7.27 (m, 2H), 6.89 – 6.82 (m,1H), 6.77 – 6.71 (m, 1H), 4.02 (t, J = 6.3 Hz, 2H), 2.35 (s, 3H), 2.00 (t, J= 7.2 Hz, 2H), 1.74 (p, J = 6.5 Hz, 2H), 1.58 (p, J = 7.3 Hz, 2H), 1.42 (p, J= 7.4, 6.6 Hz, 2H). 13C NMR (101 MHz, DMSO) δ 169.49, 159.46, 145.57, 144.44,135.94, 135.78, 130.17, 126.49, 118.23, 115.36, 115.21, 114.30, 111.55,109.23, 67.75, 32.72, 28.96, 25.68, 25.40, 21.32. HRMS (AP-ESI) m / z, calcdfor C20H23N3O3, ([M+H]+): 354.1818, found: 354.1821.

[0112] Example 26. N-hydroxy-7-(3-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)heptamide (HDDI-25) Synthesized according to the target compound HDDI-1, pink solid, yield: 53%, mp 175-177℃. 1H NMR (400 MHz, DMSO-d6) δ 10.37 (s, 1H), 8.71 (s, 1H), 8.39 (d, J = 6.8 Hz, 1H), 8.32 (s, 1H), 7.50 (d, J = 6.6 Hz, 2H), 7.32 (dd, J = 14.8, 6.6 Hz, 2H), 6.90– 6.80 (m, 1H), 6.75 (d, J = 6.8 Hz, 1H), 4.02 (t, J = 6.3 Hz, 2H), 2.36 (s,3H), 1.97 (t, J = 7.3 Hz, 2H), 1.73 (p, J = 6.2 Hz, 2H), 1.53 (p, J = 7.4 Hz, 2H), 1.44 (dt, J = 14.6, 7.4 Hz, 2H), 1.33 (q, J = 6.9, 6.4 Hz, 2H). 13C NMR (100 MHz, DMSO-d6), δ 169.10, 159.02, 145.11, 143.97, 135.46, 135.33, 129.70,126.03, 117.76, 114.88, 114.75, 113.87, 111.10, 108.77, 67.34, 32.23, 28.65,28.36, 25.29, 25.10, 20.85. HRMS (AP-ESI) m / z, calcd for C21H25N3O3, ([M+H]+): 368.1974, found: 368.1973.

[0113] Example 27. N-hydroxy-8-(3-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)octamide (HDDI-26) Following the synthesis of the target compound HDDI-1, a white solid was produced in 46% yield at mp 163-165 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.35 (s, 1H), 8.69 (s, 1H), 8.39 (d, J = 6.8 Hz, 1H), 8.32 (s, 1H), 7.50 (d, J = 5.8 Hz, 2H), 7.39 – 7.25 (m, 2H), 6.91 – 6.81 (m,1H), 6.75 (d, J = 6.6 Hz, 1H), 4.02 (t, J = 6.4 Hz, 2H), 2.36 (s, 3H), 1.95(t, J = 7.3 Hz, 2H), 1.80 – 1.67 (m, 2H), 1.51 (dt, J = 14.8, 7.5 Hz, 2H), 1.46 – 1.38 (m, 2H), 1.30 (dq, J = 17.5, 6.0, 4.6 Hz, 4H). 13C NMR (100 MHz, DMSO-d6), δ 169.14, 159.05, 145.08, 143.90, 135.45, 135.40, 129.73, 126.07,117.76, 114.85, 114.81, 113.89, 111.11, 108.81, 67.37, 32.26, 28.73, 28.56,28.52, 25.46, 25.09, 20.86. HRMS (AP-ESI) m / z, calcd for C22H27N3O3, ([M+H]+): 382.2131, found: 382.2135.

[0114] Example 28. N-hydroxy-4-((3-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy)methyl)benzamide (HDDI-27) Following the synthesis of the target compound HDDI-1, a white solid was obtained, yielding 79%, with an mp of 211-213 °C. 1H NMR (400 MHz, DMSO-d6) δ 11.24 (s, 1H), 9.06 (s, 1H), 8.40 (d, J = 6.9 Hz, 1H), 8.32 (s, 1H), 7.79 (d, J = 8.0 Hz, 2H), 7.62 (q, J = 2.2 Hz, 1H), 7.55 (dd, J= 13.1, 7.8 Hz, 3H), 7.39 – 7.30 (m, 2H), 6.96 (dd, J = 8.1, 2.6 Hz, 1H), 6.75 (dd, J = 7.0, 1.6 Hz, 1H), 5.24 (s, 2H), 2.36 (s, 3H). 13C NMR (101 MHz, DMSO) δ 164.01, 158.55, 145.11, 143.81, 140.38, 135.55, 135.46, 132.21,129.80, 127.34, 127.05, 126.08, 118.24, HRMS(AP-ESI) m / z, calcd for C22H19N3O3, ([M+H]+): 374.1505, found: 374.1508.

[0115] Example 29. (E)-N-hydroxy-3-[4-[[3-(7-methylimidazo[1,2-α]pyridin-2-yl)phenoxy]methyl]phenyl]acrylamide (HDDI-28) Following the synthesis of the target compound HDDI-1, a white solid was obtained in 69% yield at mp 211-213 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.78 (s, 1H), 9.07 (s, 1H), 8.40 (d, J = 6.9 Hz, 1H), 8.31 (s, 1H), 7.60 (d, J = 8.0 Hz, 3H), 7.53 (d, J = 7.5 Hz, 3H), 7.48 (d, J= 15.7 Hz, 1H), 7.39 – 7.30 (m, 2H), 6.95 (dd, J = 8.2, 2.6 Hz, 1H), 6.74(dd, J = 6.9, 1.6 Hz, 1H), 6.48 (d, J = 15.8 Hz, 1H), 5.21 (s, 2H), 2.36 (s,3H). 13C NMR (101 MHz, DMSO) δ 162.72, 158.62, 145.14, 143.89, 138.58,137.99, 135.58, 135.41, 134.32, 129.80, 128.09, 127.61, 126.08, 119.15,118.19, 114.91, 114.80, 114.16, 111.57, 108.84, 68.76, 20.88. HRMS (AP-ESI)m / z, calcd for C24H21N3O3, ([M+H]+): 400.1661, found: 400.1665.

[0116] Example 30. 2-(4-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)-N-hydroxyacetamide (HDDI-29) Following the synthesis of the target compound HDDI-1, a white solid was obtained, yielding 85% with an mp value of 197-199 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.89 (s, 1H), 9.03 (s, 1H), 8.86 (s, 1H), 8.27 (s, 1H), 7.90 (d, J = 8.7 Hz, 2H), 7.55 (d, J = 9.5 Hz, 1H), 7.35 (dd, J = 9.5, 1.6Hz, 1H), 7.04 (d, J = 8.7 Hz, 2H), 4.52 (s, 2H). 13C NMR (100 MHz, DMSO-d6), δ 164.23, 157.76, 145.09, 143.26, 127.57, 126.93, 126.71, 126.63, 117.43,114.96, 108.65, 105.72, 65.90. HRMS (AP-ESI) m / z, calcd for C15H12BrN3O3, ([M+H]+): 362.0140, found: 362.0140 Example 31. 4-(4-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)-N-hydroxybutyramide (HDDI-30) The target compound HDDI-1 was synthesized as a yellow solid, yield: 93%, mp 233-235℃. 1H NMR(400 MHz, DMSO-d6) δ 10.45 (s, 1H), 8.89 – 8.81 (m, 1H), 8.74 (s, 1H), 8.25(s, 1H), 7.88 (d, J = 8.7 Hz, 2H), 7.54 (d, J = 9.5 Hz, 1H), 7.34 (dd, J =9.5, 1.9 Hz, 1H), 7.00 (d, J = 8.8 Hz, 2H), 4.01 (t, J = 6.3 Hz, 2H), 2.15(t, J = 7.4 Hz, 2H), 1.96 (p, J = 6.7 Hz, 2H). 13C NMR (100 MHz, DMSO-d6), δ168.64, 158.56, 145.24, 143.25, 127.53, 127.02, 126.70, 125.96, 117.41,114.74, 108.50, 105.69, 66.87, 28.75, 24.84. HRMS (AP-ESI) m / z, calcd forC17H16BrN3O3, ([M+H]+): 390.0453, found: 390.0450.

[0117] Example 32. 5-(4-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)-N-hydroxypentanamide (HDDI-31) Following the synthesis of the target compound HDDI-1, a light yellow solid was produced in 88% yield at mp 206-208 °C. 1HNMR (400 MHz, DMSO-d6) δ 10.39 (s, 1H), 8.85 (s, 1H), 8.71 (s, 1H), 8.25 (s,1H), 7.87 (d, J = 8.6 Hz, 2H), 7.54 (d, J = 9.5 Hz, 1H), 7.38 – 7.26 (m, 1H),7.00 (d, J = 8.6 Hz, 2H), 4.01 (t, J = 5.9 Hz, 2H), 2.03 (t, J = 6.9 Hz, 2H),1.70 (tt, J = 12.0, 6.0 Hz, 4H). 13C NMR (100 MHz, DMSO-d6), δ 168.90,158.62, 145.27, 143.24, 127.48, 126.98, 126.67, 125.87, 117.39, 114.70,108.46, 105.65, 67.10, 31.91, 28.18, 21.79. HRMS (AP-ESI) m / z, calcd forC18H18BrN3O3, ([M+H]+): 404.0610, found: 404.0613.

[0118] Example 33. 6-(4-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)-N-hydroxyhexanoamide (HDDI-32) Following the synthesis of the target compound HDDI-1, a light yellow solid was produced in 88% yield at mp 199-201 °C. 1HNMR (400 MHz, DMSO-d6) δ 10.40 (s, 1H), 8.86 (s, 1H), 8.70 (s, 1H), 8.26 (s,1H), 7.87 (d, J = 8.7 Hz, 2H), 7.55 (d, J = 9.5 Hz, 1H), 7.34 (dd, J = 9.5,1.8 Hz, 1H), 7.00 (d, J = 8.7 Hz, 2H), 3.99 (t, J = 6.4 Hz, 2H), 1.99 (t, J =7.3 Hz, 2H), 1.73 (p, J = 6.5 Hz, 2H), 1.57 (p, J = 7.4 Hz, 2H), 1.40 (p, J =7.6, 6.9 Hz, 2H). 13C NMR (100 MHz, DMSO-d6), δ 169.02, 158.67, 145.23,143.22, 127.52, 127.00, 126.69, 125.80, 117.37, 114.68, 108.48, 105.68,67.40, 32.24, 28.45, 25.19, 24.92. HRMS (AP-ESI) m / z, calcd for C19H20BrN3O3,([M+H]+): 418.0766, found: 418.0768.

[0119] Example 34. 7-(4-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)-N-hydroxyheptanamide (HDDI-33) The synthesis of the target compound HDDI-1 was performed as follows: white solid, yield: 91%, mp 204-206℃. 1H NMR (400 MHz, DMSO-d6) δ 10.35 (s, 1H), 8.86 (s, 1H), 8.67 (s, 1H), 8.38 (s, 1H), 7.58 (d, J = 9.5 Hz, 1H), 7.53 – 7.49 (m, 2H), 7.40 – 7.30 (m, 2H), 6.89 (d,J = 8.0 Hz, 1H), 4.02 (t, J = 5.6 Hz, 2H), 1.96 (t, J = 7.3 Hz, 2H), 1.80 –1.67 (m, 2H), 1.58 – 1.49 (m, 2H), 1.47 – 1.38 (m, 2H), 1.32 (q, J = 7.5 Hz,2H). 13C NMR (100 MHz, DMSO-d6), δ 169.04, 158.68, 145.30, 143.26, 127.49,127.00, 126.68, 125.84, 117.40, 114.69, 108.46, 105.67, 67.44, 40.20, 32.24,28.60, 28.36, 25.27, 25.10. HRMS (AP-ESI) m / z, calcd for C20H22BrN3O3, ([M+H]+): 432.0923, found: 432.0927.

[0120] Example 35. 8-(4-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)-N-hydroxyoctamide (HDDI-34) Following the synthesis of the target compound HDDI-1, a light yellow solid was produced in 72% yield at mp 178-180 °C. 1HNMR (400 MHz, DMSO-d6) δ 10.34 (s, 1H), 8.88 – 8.81 (m, 1H), 8.67 (s, 1H), 8.25 (s, 1H), 7.87 (d, J = 8.7 Hz, 2H), 7.54 (d, J = 9.5 Hz, 1H), 7.34 (dd, J= 9.5, 1.8 Hz, 1H), 7.00 (d, J = 8.7 Hz, 2H), 4.00 (t, J = 6.5 Hz, 2H), 1.95(t, J = 7.3 Hz, 2H), 1.72 (p, J = 6.6 Hz, 2H), 1.50 (p, J = 7.3 Hz, 2H), 1.41(p, J = 6.8 Hz, 2H), 1.36 – 1.22 (m, 4H). 13C NMR (101 MHz, DMSO-d6) δ169.09, 158.68, 145.26, 143.22, 127.47, 126.98, 126.65, 125.80, 117.37,114.68, 108.44, 105.64, 67.46, 32.23, 28.64, 28.52, 28.46, 25.41, 25.05. HRMS(AP-ESI) m / z, calcd for C21H24BrN3O3, ([M+H]+): 446.1079, found: 446.1083.HRMS (AP-ESI) m / z, calcd for C21H24BrN3O3, ([M+H]+): 446.1079, found: 446.1083.

[0121] Example 36. 2-(3-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)-N-hydroxyacetamide (HDDI-35) The target compound HDDI-1 was synthesized as a white solid, yield: 89%, mp 219-221℃. 1H NMR(400 MHz, DMSO-d6) δ 10.92 (s, 1H), 9.02 (s, 1H), 8.90 (s, 1H), 8.38 (s, 1H),7.64 – 7.52 (m, 3H), 7.43 – 7.32 (m, 2H), 7.00 – 6.91 (m, 1H), 4.56 (s, 2H).13C NMR (100 MHz, DMSO-d6), δ 164.28, 158.24, 144.85, 143.24, 134.81, 129.84,127.91, 126.90, 118.67, 117.68, 114.45, 111.70, 109.85, 106.00, 65.88. HRMS(AP-ESI) m / z, calcd for C15H12BrN3O3, ([M+H]+): 362.0140, found: 362.0141.

[0122] Example 37. 4-(3-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)-N-hydroxybutyramide (HDDI-36) Following the synthesis of the target compound HDDI-1, a white solid was obtained in 65% yield at mp 189-191 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.46 (s, 1H), 8.86 (s, 1H), 8.74 (d, J = 8.1 Hz, 1H), 8.38 (s, 1H), 7.58 (d, J = 9.5 Hz, 1H), 7.52 (d, J = 6.5 13C NMR (100 MHz, DMSO-d6), δ 168.66, 158.96,144.99, 143.24, 134.79, 129.88, 127.88, 126.85, 118.04, 117.70, 114.43,111.26, 109.83, 105.99, 66.80, 52.62, 40.20, 28.75, 24.88. HRMS (AP-ESI) m / z,calcd for C17H16BrN3O3, ([M+H]+): 390.0453, found: 390.0457.

[0123] Example 38. 5-(3-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)-N-hydroxypentanamide (HDDI-37) The target compound HDDI-1 was synthesized as a yellow solid, yield: 76%, mp 186-188℃. 1H NMR (400 MHz, DMSO-d6) δ 10.42 (s, 1H), 8.87 (s, 1H), 8.74 (s, 1H), 8.39 (s, 1H), 7.58 (d, J = 9.5 Hz, 1H), 7.56 – 7.49 (m, 2H), 7.42 – 7.29 (m, 2H), 6.95 –6.86 (m, 1H), 4.04 (t, J = 5.7 Hz, 2H), 2.05 (t, J = 6.8 Hz, 2H), 1.71 (dd, J= 12.4, 6.4 Hz, 4H). 13C NMR (100 MHz, DMSO-d6), δ 168.91, 159.03, 145.01,143.22, 134.78, 129.85, 127.85, 126.83, 117.96, 117.68, 114.43, 111.23,109.82, 105.97, 67.03, 31.91, 28.21, 21.79. HRMS (AP-ESI) m / z, calcd forC18H18BrN3O3, ([M+H]+): 404.0610, found: 404.0614.

[0124] Example 39. 6-(3-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)-N-hydroxyhexanoamide (HDDI-38) Following the synthesis of the target compound HDDI-1, a white solid was obtained, yielding 54% at mp 172-174 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.39 (s, 1H), 8.86 (s, 1H), 8.72 (s, 1H), 8.39 (s, 1H), 7.58 (d, J = 9.5 Hz, 1H), 7.54 – 7.48 (m, 2H), 7.42 – 7.29 (m, 2H), 6.95 –6.84 (m, 1H), 4.02 (t, J = 6.4 Hz, 2H), 2.00 (t, J = 7.2 Hz, 2H), 1.74 (p, J= 6.6 Hz, 2H), 1.58 (p, J = 7.3 Hz, 2H), 1.42 (p, J = 7.3, 6.6 Hz, 2H). 13CNMR (100 MHz, DMSO-d6), δ 169.01, 159.05, 145.02, 143.21, 134.77, 129.85,127.84, 126.82, 117.93, 117.68, 114.36, 111.23, 109.82, 105.96, 67.33, 32.25,28.47, 25.20, 24.92. HRMS (AP-ESI) m / z, calcd for C19H20BrN3O3, ([M+H]+): 418.0766, found: 418.0768.

[0125] Example 40. 7-(3-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)-N-hydroxyheptanamide (HDDI-39) Following the synthesis of the target compound HDDI-1, a yellow solid was obtained, yielding 44% at mp 161-163 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.35 (s, 1H), 8.86 (s, 1H), 8.67 (d, J = 4.4 Hz, 1H), 8.38 (s, 1H), 7.58 (d, J = 9.5 Hz, 1H), 7.54 – 7.49 (m, 2H), 7.42 – 7.29 (m,2H), 6.89 (dd, J = 7.8, 2.3 Hz, 1H), 4.08 – 3.97 (m, 2H), 1.96 (t, J = 7.3Hz, 2H), 1.73 (p, J = 6.4 Hz, 2H), 1.53 (p, J = 7.4 Hz, 2H), 1.48 – 1.39 (m,2H), 1.32 (q, J = 7.5 Hz, 2H). 13C NMR (100 MHz, DMSO-d6), δ 169.11, 159.07,145.02, 143.22, 134.77, 129.85, 127.84, 126.83, 117.92, 117.68, 114.38,111.23, 109.83, 105.97, 67.37, 32.22, 28.63, 28.36, 25.28, 25.09. HRMS (AP-ESI) m / z, calcd for C20H22BrN3O3, ([M+H]+): 432.0923, found: 432.0927.

[0126] Example 41. 8-(3-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)-N-hydroxyoctamide (HDDI-40) Following the synthesis of the target compound HDDI-1, a pale yellow solid was obtained in 80% yield at mp 156-158 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.35 (s, 1H), 8.87 (s, 1H), 8.69 (s, 1H), 8.39 (s, 1H), 7.58 (d, J = 9.5 Hz, 1H), 7.51 (s, 2H), 7.40 – 7.30 (m, 2H), 6.96 – 6.84 (m,1H), 4.03 (t, J = 6.3 Hz, 2H), 1.95 (t, J = 7.2 Hz, 2H), 1.74 (p, J = 6.6 Hz,2H), 1.52 (q, J = 7.2 Hz, 2H), 1.46 – 1.38 (m, 2H), 1.32 (dq, J = 19.3, 7.2Hz, 4H). 13C NMR (100 MHz, DMSO-d6), δ 169.11, 159.08, 145.03, 143.21,134.77, 129.84, 127.83, 126.82, 117.91, 117.68, 114.38, 111.24, 109.82,105.96, 67.41, 32.25, 28.70, 28.54, 28.49, 25.43, 25.07. HRMS (AP-ESI) m / z,calcd for C21H24BrN3O3, ([M+H]+): 446.1079, found: 446.1082.

[0127] Example 42. 4-((3-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)methyl)-N-hydroxybenzamide (HDDI-41) The target compound HDDI-1 was synthesized as a white solid with a yield of 43% and an mp of 101-103 °C. 1H NMR (400 MHz, DMSO-d6) δ 11.24 (s, 1H), 9.06 (s, 1H), 8.88 (s, 1H), 8.38 (s, 1H), 7.79 (d, J = 8.0 Hz, 2H), 7.70 – 7.47 (m, 5H), 7.37 (ddt, J = 7.9, 4.9, 2.6Hz, 2H), 7.00 (dd, J = 8.1, 2.7 Hz, 1H), 5.25 (s, 2H). 13C NMR (101 MHz, DMSO) δ 164.00, 158.61, 144.90, 143.25, 140.31, 134.89, 132.22, 129.96,127.93, 127.34, 127.06, 126.89, 118.42, 117.70, 114.67, 111.73, 109.89,106.02, 68.63, 40.15, 39.94, 39.73, 39.52, 39.31, 39.10, 38.89. HRMS (AP-ESI)m / z, calcd for C21H16BrN3O3, ([M+H]+): 438.0453, found: 438.0455.

[0128] Example 43. (E)-3-(4-((3-(6-bromoimidazolo[1,2-α]pyridin-2-yl)phenoxy)methyl)phenyl)-N-hydroxyacrylamide (HDDI-42) Following the synthesis of the target compound HDDI-1, a white solid was obtained in 60% yield at mp 180-182 °C. 1H NMR(400 MHz, DMSO-d6) δ 10.78 (s, 1H), 9.07 (s, 1H), 8.88 (s, 1H), 8.38 (s, 1H),7.68 – 7.42 (m, 8H), 7.40 – 7.32 (m, 2H), 6.99 (dd, J = 8.2, 2.5 Hz, 1H),6.48 (d, J = 15.8 Hz, 1H), 5.22 (s, 2H). 13C NMR (101 MHz, DMSO) δ 162.70,158.67, 144.93, 143.25, 138.50, 137.97, 134.88, 134.33, 129.95, 128.08,127.91, 127.60, 126.88, 119.16, 118.37, 117.70, 114.69, 111.73, 109.87,106.01, 68.80. HRMS (AP-ESI) m / z, calcd for C23H18BrN3O3, ([M+H]+): 464.0610, found: 464.0614.

[0129] Activity evaluation of target compounds Experimental Example 1. Experiment on the inhibition of HDAC1 by the target compound. 1. Materials: HDAC1 enzyme (Active Motif), fluorescent substrate (Ac-Leu-Gly-Lys(Ac)MCA, Shanghai Bid Pharmaceutical Technology Co., Ltd.), trypsin (Solepro), 96-well plate; 2. Method: The compound was diluted with HDAC buffer to prepare compound solutions of different concentration gradients. Three groups were set up: experimental group: 50 μL compound solution + 20 μL HDAC1 enzyme + 30 μL 33.35 μM fluorescent substrate; 100% group: 50 μL HDAC buffer + 20 μL HDAC1 enzyme + 30 μL 33.35 μM fluorescent substrate; 0% group: 50 μL HDAC buffer + 20 μL HDAC buffer + 30 μL 33.35 μM fluorescent substrate. The compound solution or HDAC buffer was added to a black 96-well plate, followed by the addition of HDAC1 enzyme. After incubation at room temperature for 5 min, the fluorescent substrate was added, and the plate was incubated at 37°C in the dark for 1 hour. After incubation, add an appropriate amount of stop solution (10 mg / mL trypsin, 20 μM TSA), and continue incubation at 37°C in the dark for 30 min. Measure the absorbance (OD) of each well at 390 / 460 nm using a microplate reader, and then calculate the inhibition rate and IC50. 50 value.

[0130] Inhibition rate (%) = (OD of 100% group - OD of experimental group) / (OD of 100% group - 0% OD); Table 2. HDAC1 inhibitory activity of the target compounds

[0131]

[0132] a The data in the table are the averages of three experiments; the values ​​after "±" represent the mean and standard deviation. 3. Conclusion: All target compounds exhibited good HDAC1 inhibitory activity, especially compounds HDDI-11 and HDDI-25, whose HDAC1 inhibitory activity was 84 times and 180 times that of the positive control drug SAHA, respectively. Specific data are shown in Table 2.

[0133] Example 2: Test for the binding of the compound to DNA 1. Materials: Calf thymus DNA (purchased from Beijing Nobride Technology Co., Ltd.), 20 mM Tris-HC1 buffer (pH=7.4), UV-Vis spectrophotometer (Shimadzu UV-2600i), fluorescence spectrophotometer (Shimadzu RF-6000), cuvettes, etc.

[0134] 2. Method: (1) Preparation of CT-DNA solution: Add CT-DNA to 20 mM Tris-HC1 buffer (pH=7.4), gently shake (do not shake violently) overnight at 4 ℃ to dissolve, and prepare a CT-DNA solution with a concentration of 1 mg / mL.

[0135] (2) Detection of the binding of compounds to DNA by ultraviolet-visible spectroscopy The baseline was calibrated using Tris-HCl buffer (20 mM, pH=7.4), and the measurement range was 200–400 nm. The CT-DNA concentration was fixed at 0.2 mg / mL (approximately 160 μM), and a certain concentration of the compound was added. The UV-Vis absorption spectrum of the mixture was then measured.

[0136] (3) Detection of the binding of compounds to DNA by fluorescence spectroscopy The baseline was calibrated using Tris-HCl buffer (20 mM, pH=7.4), and the measurement range was 300-600 nm. The CT-DNA concentration was fixed at 0.2 mg / mL (approximately 160 μM), and a certain concentration of the compound was added. The maximum UV absorption wavelength of the compound was fixed as the excitation wavelength, and the fluorescence emission spectrum of the mixture was measured.

[0137] 3. Conclusion: (e.g.) Figure 1 As shown, the active compounds HDDI-11 and HDDI-25 can effectively bind to CT-DNA, while the HDAC inhibitor SAHA cannot bind to CT-DNA.

[0138] Experimental Example 3: Anti-tumor cell proliferation activity and normal cytotoxicity of the target compound 1. Materials: Tumor cells (HEL, MV4-11, A549) and normal cells (293T), CCK-8 cell viability assay kit, 10% fetal bovine serum (Hyclone, USA), 2.5 g∙L⁻¹ trypsin (Gibco, USA), modified RPMI 1640 medium (Hyclone, USA), 96-well plates; 2. Method: Cells were cultured using standard methods. Logarithmically growing cells were seeded into 96-well plates (100 μL per well) and incubated for 8 hours in a constant temperature incubator (37 ℃, 5% CO2). A specific concentration of the target compound solution was then added, and the cells were cultured for another 48 hours. 20 μL of CCK-8 was then added, and the cells were incubated for 2-3 hours. The absorbance of each well was measured at 450 nm using a microplate reader, and the inhibition rate and IC50 were calculated. 50 value; Inhibition rate (%) = (Average OD value of 100% wells - Average OD value of experimental wells) / (Average OD value of 100% wells - Average OD value of blank wells) Table 3. Results of in vitro experiments on the inhibition of tumor cell proliferation by the target compound.

[0139] a The data in the table are the averages of three experiments; the values ​​after "±" represent SEM values. Terminology: HEL, human erythroleukemia cells; MV4-11, human myeloid monocytic leukemia cells; A549, human lung adenocarcinoma cells; 293T, human embryonic kidney cells; 3. Conclusion: In all tumor cell types tested, all target compounds exhibited superior antiproliferative activity compared to the positive control SAHA. Compounds HDDI-11 and HDDI-25 showed significantly better inhibitory activity against HEL cell proliferation (0.0055 μM and 0.0032 μM, respectively) than the positive control SAHA (IC50 = 0.10 μM). Furthermore, HDDI-25 showed weak toxicity to normal 293T cells (IC50 = 0.10 μM). 50 =11.96 μM), comparable to the positive control drug SAHA (IC50). 50 = 13.8 μM). See Table 3 for specific data.

[0140] The above compounds can be further studied for activity, and more active compounds can be developed for the preparation of cancer prevention and treatment.

Claims

1. A 2-phenylimidazo[1,2-] α ]Pyridine derivatives, wherein the derivatives are selected from any one of the following: N -hydroxy-4-(4-(imidazo[1,2-) α ]pyridin-2-yl)phenoxy)butyramide (HDDI-2); N -hydroxy-5-(4-(imidazo[1,2-) α ]Pyridin-2-yl)phenoxy)pentanamide (HDDI-3); N -hydroxy-6-(4-(imidazo[1,2-) α ]pyridin-2-yl)phenoxy)hexamamide (HDDI-4); N -hydroxy-7-(4-(imidazo[1,2-) α ]pyridin-2-yl)phenoxy)heptamide (HDDI-5); N -hydroxy-8-(4-(imidazo[1,2-) α ]pyridin-2-yl)phenoxy)octamide (HDDI-6); N -hydroxy-5-(3-(imidazo[1,2-) α ]Pyridin-2-yl)phenoxy)pentanamide (HDDI-9); N -hydroxy-6-(3-(imidazo[1,2-) α ]Pyridin-2-yl)phenoxy)hexamamide (HDDI-10); N -hydroxy-7-(3-(imidazo[1,2-) α ]Pyridin-2-yl)phenoxy)heptamide (HDDI-11); N -hydroxy-8-(3-(imidazo[1,2-) α ]pyridin-2-yl)phenoxy)octamide (HDDI-12); N -hydroxy-4-((3-(imidazo[1,2-) α ]pyridin-2-yl)phenoxy)methyl)benzamide (HDDI-13); ( E )- N -hydroxy-3-(4-((3-(imidazo[1,2-) α ]pyridin-2-yl)phenoxy)methyl)phenyl)acrylamide (HDDI-14); N -hydroxy-6-(4-(7-methylimidazo[1,2-] α ]pyridin-2-yl)phenoxy)hexamamide (HDDI-18); N -hydroxy-7-(4-(7-methylimidazo[1,2-] α ]Pyridin-2-yl)phenoxy)heptamide (HDDI-19); N -hydroxy-8-(4-(7-methylimidazo[1,2-] α ]Pyridin-2-yl)phenoxy)octamide (HDDI-20); N -hydroxy-6-(3-(7-methylimidazo[1,2-) α ]Pyridin-2-yl)phenoxy)hexamamide (HDDI-24); N -hydroxy-7-(3-(7-methylimidazo[1,2-] α ]Pyridin-2-yl)phenoxy)heptamide (HDDI-25); N -hydroxy-8-(3-(7-methylimidazo[1,2-] α ]pyridin-2-yl)phenoxy)octamide (HDDI-26); N -hydroxy-4-((3-(7-methylimidazo[1,2-) α ]pyridin-2-yl)phenoxy)methyl)benzamide (HDDI-27); ( E )- N -hydroxy-3-(4-((3-(7-methylimidazo[1,2-) α ]Pyridin-2-yl)phenoxy)methyl)phenyl)acrylamide (HDDI-28); 6-(4-(6-bromoimidazole[1,2-) α ]pyridin-2-yl)phenoxy)- N - Hydroxyhexamethylene amide (HDDI-32); 7-(4-(6-bromoimidazole[1,2- α ]pyridin-2-yl)phenoxy)- N -Hydroxyheptaamide (HDDI-33); 8-(4-(6-bromoimidazole[1,2- α ]pyridin-2-yl)phenoxy)- N -Hydroxyoctamide (HDDI-34); 5-(3-(6-bromoimidazole[1,2- α ]pyridin-2-yl)phenoxy)- N - Hydroxypentamide (HDDI-37); 6-(3-(6-bromoimidazole[1,2-) α ]pyridin-2-yl)phenoxy)- N - Hydroxyhexamethyleneamide (HDDI-38); 7-(3-(6-bromoimidazole[1,2- α ]pyridin-2-yl)phenoxy)- N -Hydroxyheptaamide (HDDI-39); 8-(3-(6-bromoimidazole[1,2- α ]pyridin-2-yl)phenoxy)- N -Hydroxyoctamide (HDDI-40); 4-((3-(7-bromoimidazole[1,2- α ]pyridin-2-yl)phenoxy)methyl)- N - Hydroxybenzamide (HDDI-41); ( E )-3-(4-((3-(7-bromoimidazole[1,2- α ]pyridin-2-yl)phenoxy)methyl)phenyl)- N - Hydroxyacrylamide (HDDI-42).

2. The method for preparing the derivative according to claim 1, characterized in that, The method includes the following steps: (a) 2-aminopyridines with different substitutions are reacted with 2-bromo-4'-hydroxyacetophenone or 2-bromo-3'-hydroxyacetophenone in an organic solvent at room temperature to generate intermediate LT1-6; (b) The intermediate LT1-6 obtained in step (a) was reacted with bromocarboxylic acid esters of different structures under alkaline conditions in an aprotic polar solvent by heating to generate the key intermediate LT7-48. (c) The intermediate LT7-48 obtained in step (b) is reacted with hydroxylamine hydrochloride and alkali metal hydroxide in a low alcohol solvent to convert the methyl ester group into an isohydroxamic acid group, thereby obtaining the target product. Wherein, the bromocarboxylic acid ester mentioned in step (b) is selected from methyl 5-bromopentanoate, methyl 6-bromohexanoate, methyl 7-bromoheptanoate, methyl 4-bromomethylbenzoate or methyl 4-bromomethylcinnamate.

3. The method as described in claim 2, characterized in that, In step (a), the organic solvent is acetone.

4. The method as described in claim 2, characterized in that, In step (b), the alkaline conditions are provided by cesium carbonate (Cs2CO3), the aprotic polar solvent is N,N-dimethylformamide (DMF), and the reaction temperature is 60~100℃.

5. The method as described in claim 2, characterized in that, In step (c), the alkali metal hydroxide is potassium hydroxide (KOH), and the lower alcohol solvent is methanol (MeOH).

6. A pharmaceutical composition, characterized in that, It comprises the derivative of claim 1, its stereoisomer or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable carriers or excipients.

7. The pharmaceutical composition of claim 6, characterized in that, The pharmaceutical composition described herein is suitable for oral or parenteral administration.

8. The use of the derivative of claim 1, its stereoisomer, or a pharmaceutically acceptable salt thereof in the preparation of a medicament for the prevention or treatment of cancer.

9. The application as described in claim 8, characterized in that, The cancer is selected from leukemia or lung cancer.

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