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Synthesis and bio-activity evaluation of 2-styryl-5-nitroimidazol derivatives containing 1,4-benzdioxan skeleton

A technology of benzodioxane and nitroimidazole is applied in the field of synthesis of novel 2-styryl-5-nitroimidazole derivatives, and can solve the problems of obvious adverse reactions, poor pharmacokinetic properties and the like

Inactive Publication Date: 2015-03-25
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, studies have found that imidazole compounds have a variety of biological activities, especially as anticancer drugs, showing broad application prospects, but they have the characteristics of poor pharmacokinetic properties and obvious adverse reactions. Effectively modify their structures to obtain high-efficiency , low toxicity imidazole anticancer drugs have become one of the hotspots in the field of medicinal chemistry

Method used

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  • Synthesis and bio-activity evaluation of 2-styryl-5-nitroimidazol derivatives containing 1,4-benzdioxan skeleton
  • Synthesis and bio-activity evaluation of 2-styryl-5-nitroimidazol derivatives containing 1,4-benzdioxan skeleton
  • Synthesis and bio-activity evaluation of 2-styryl-5-nitroimidazol derivatives containing 1,4-benzdioxan skeleton

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Example 1: (Z)-2-(2-(2-chlorostyryl)-5-nitroimidazole)ethyl 2,3-dihydrobenzo[b][1,4]dioxa Preparation of cyclohexene-5-carboxylic acid (3a)

[0016]

[0017] After dissolving catechin (1 mmol) in methanol (30 ml), concentrated sulfuric acid (0.5 ml) was added dropwise and kept overnight at 90°C. After the reaction, the solvent was removed, the organic layer was dissolved with ethyl acetate (20ml), and then extracted with water (40ml), the organic layer was dried with anhydrous sodium sulfate, the solvent was removed under reduced pressure, and a solid was precipitated. The solid was recrystallized from ethanol to obtain compound 1, filled with nitrogen, dissolved compound 1 (1mmol) in anhydrous acetone (10ml), then added anhydrous potassium carbonate (2mmol), and added dropwise a mixed solution of dibromomethane (1mmol) and acetone , reflux reaction for 24 hours. After the reaction solution was distilled off under reduced pressure, an appropriate amount of water wa...

Embodiment 2

[0021] Example 2: (Z)-2-(2-(3-chlorostyryl)-5-nitroimidazole)ethyl 2,3-dihydrobenzo[b][1,4]dioxa Preparation of cyclohexene-5-carboxylic acid (3b)

[0022]

[0023] The preparation method is the same as that in Example 1, and the target compound 3b is obtained by replacing o-chlorobenzaldehyde with m-chlorobenzaldehyde. Yield 64.5%.m.p.188~189℃; 1 H NMR (DMSO-d 6 , 300MHz) δ: 8.25(s, 1H), 8.01(t, J=7.1Hz, 2H), 7.77-7.69(m, 2H), 7.42(t, J=7.5Hz, 1H), 7.17(t, J =7.6Hz, 1H), 6.93(d, J=7.8Hz, 1H), 6.42(d, J=7.9Hz, 2H), 5.06(t, J=4.4Hz, 2H), 4.75(t, J=4.2 Hz, 2H), 4.17(s, 4H).

Embodiment 3

[0024] Example 3: (Z)-2-(2-(4-chlorostyryl)-5-nitroimidazole)ethyl 2,3-dihydrobenzo[b][1,4]dioxa Preparation of cyclohexene-5-carboxylic acid (3c)

[0025]

[0026] The preparation method is the same as in Example 1, and p-chlorobenzaldehyde is used instead of o-chlorobenzaldehyde to obtain the target compound 3c. Yield 67.5%.m.p.187~189℃; 1 H NMR (DMSO-d 6 , 300MHz) δ: 8.25(s, 1H), 7.89(s, 1H), 7.71(d, J=12.3Hz, 1H), 7.64-7.61(m, 1H), 7.52(d, J=7.6Hz, 1H ), 7.42(d, J=6.8Hz, 2H), 7.11(d, J=7.9Hz, 1H), 6.91(d, J=8.1Hz, 1H), 6.53-6.48(m, 1H), 5.02(t , J=8.4Hz, 2H), 4.57(t, J=8.2Hz, 2H), 4.13(s, 4H).

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Abstract

The invention provides a synthesis method of 2-styryl-5-nitroimidazol derivatives containing a 1, 4-benzdioxan skeleton. The 2-styryl-5-nitroimidazol derivatives containing 1,4-benzdioxan skeleton are characterized in that the formula is as described in the specification, wherein R=3a: o-Cl; 3b: m-Cl; 3c: p-Cl; 3d: o-Br; 3e: m-Br; 3f: p-Br; 3g: o-F; 3h: m-F; 3i: p-F; 3j: o-CH3; 3k: m-CH3; 3l: p-CH3; 3m: o-OCH3; 3n: m-OCH3; 3o: p-OCH3; 3p: 2-F-6-Cl; 3q: fused pH; 3r: H. The invention also discloses a preparation method of the 2-styryl-5-nitroimidazol derivatives containing 1,4-benzdioxan skeleton.

Description

technical field [0001] The present invention relates to the synthesis of a class of novel 2-styryl-5-nitroimidazole derivatives containing 1,4-benzodioxane skeleton and the research on their anticancer activity. Background technique [0002] Imidazole derivatives, which are widely used in the treatment of anaerobic infections, can treat intestinal and parenteral amoebiasis (such as amebic liver abscess, pleural amoebiasis, etc.), vaginal trichomoniasis, balanomiasis Wait. In recent years, studies have found that imidazole compounds have a variety of biological activities, especially as anticancer drugs, showing broad application prospects, but they have the characteristics of poor pharmacokinetic properties and obvious adverse reactions. Effectively modify their structures to obtain high-efficiency Imidazole anticancer drugs with low toxicity and low toxicity have become one of the research hotspots in the field of medicinal chemistry. [0003] 1,4-Benzodioxane contains tw...

Claims

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Application Information

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IPC IPC(8): C07D405/12A61P35/00
CPCC07D405/12
Inventor 朱海亮陶翔翔段勇涛汤丹洁桑亚丽
Owner NANJING UNIV
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