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2-(((1H-indole-3-yl) methoxyl) methyl)-1H-benzimidazole derivatives and preparation thereof

A technology of benzimidazoles and derivatives, which is applied in the field of medicinal chemistry and can solve the problems of few types of compounds and the like

Inactive Publication Date: 2016-05-18
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Literature (ShaukatA, MirzaHM, AnsariAH, etal. Benzmidazole derivatives: synthesis, leishmanicidaeffectiveness, and molecular dockingstudies [J]. Medicinal Chemistry Research, 2013, 22(8): 3606-3620.) reported a class of indole-containing compounds with high antitumor activity - the synthesis of benzimidazole structure compound, but up to now, indole-benzimidazole compound kind is very few, and the indole-benzimidazole derivatives and preparation method thereof of ether bond linkage have not been reported in domestic and foreign literature

Method used

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  • 2-(((1H-indole-3-yl) methoxyl) methyl)-1H-benzimidazole derivatives and preparation thereof
  • 2-(((1H-indole-3-yl) methoxyl) methyl)-1H-benzimidazole derivatives and preparation thereof
  • 2-(((1H-indole-3-yl) methoxyl) methyl)-1H-benzimidazole derivatives and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Example 1: Add 1.19g of 1-benzylindole-3-methanol and 10ml of tetrahydrofuran to a 50ml three-necked flask, start stirring, slowly add 10ml of tetrahydrofuran solution containing 0.83g of 2-chloromethylbenzimidazole dropwise at room temperature, and heat up to At 60°C, add 1.0 g of potassium carbonate powder and react for 4 hours. After the reaction is complete, filter, concentrate the filtrate, and separate by column chromatography to obtain 1.15g of 2-(((1-benzyl-1H-indol-3-yl)methoxy)methyl)-1H-benzimidazole , yield 62.7%.

Embodiment 2

[0016] Example 2: Add 1.19g of 1-benzylindole-3-methanol and 10ml of dioxane to a 50ml three-necked flask, start stirring, and slowly add 1.06g of 2-chloromethyl-5-nitrobenzimidazole dropwise at room temperature 10ml of dioxane solution, heated up to 80°C, added 1.0g of potassium carbonate powder, and reacted for 4h. After the reaction is complete, filter, concentrate the filtrate, and separate by column chromatography to obtain 1.11g of 2-(((1-benzyl-1H-indol-3-yl)oxy)methyl)-5-nitro-1H - Benzimidazole, yield 53.9%.

Embodiment 3

[0017] Example 3: Add 0.94g of 1-allylindole-3-methanol and 10ml of N,N-dimethylformamide to a 50ml three-necked flask, start stirring, and slowly add 0.82g of 2-chloromethyl-5 - 10ml of N,N-dimethylformamide solution of methylbenzimidazole, heated up to 100°C, added 1.0g of potassium carbonate powder, and reacted for 5h. After the reaction is complete, filter, concentrate the filtrate, and separate by column chromatography to obtain 1.15g of 2-(((1-allyl-1H-indol-3-yl)methoxy)methyl)-5-methyl -1H-benzimidazole, yield 69.5%.

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Abstract

The invention provides 2-(((1H-indole-3-yl) methoxyl) methyl)-1H-benzimidazole derivatives represented as a general formula shown in the specification. Substituent groups R1 and R7 in the formula can be -H, -CH3, -CH2CH3, -CHCH=CH2, -CH2Ph, -COCH3 and p-CH3-C6H4-SO2-; R2, R3, R4, R5, R6, R8, R9, R10 and R11 can be -H, -CH3, -CH2CH3, -CHCH=CH2, -CH2Ph,-COCH3, -CF3, -CCl3, -CN, -NHCH3, -NO2, -OCH3, -CH2NH2, -COOCH3 and -CONHCH3. According to a method, indole-3-methanol, a derivative of indole-3-methanol, 2-chloromethylbenzimidazole and a derivative of 2-chloromethylbenzimidazole are adopted as reactants, or 3-chloromethyl indole, a derivative of 3-chloromethyl indole, benzimidazole-2-methanol and a derivative of benzimidazole-2-methanol are adopted as the reactants, the reactants have a one-step reaction under the conditions of an appropriate solvent and an appropriate catalyst, and the 2-(((1H-indole-3-yl) methoxyl) methyl)-1H-benzimidazole derivatives are generated. The preparation of the compounds is shown in the specification, wherein an X group in the formula is chlorine, bromine or iodine.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to 2-(((1H-indol-3-yl)methoxy)methyl)-1H-benzimidazole derivatives and a preparation method thereof. Background technique [0002] Indole and benzimidazole compounds are widely used in medicine, pesticides, dyes and other fields due to their activity as natural compounds. Therefore, they have also become a hot spot in the research of heterocyclic compounds, and their prospects are very broad. Many studies have also shown that compounds containing indole and benzimidazole structural fragments have good antitumor activity, such as indole derivatives Sunitinib (Sunitinib), Motesanib (Motesanib) and benzimidazole derivatives. Dovitinib and others are effective anti-cancer drugs that have been marketed at present. [0003] Literature (ShaukatA, MirzaHM, AnsariAH, etal. Benzmidazole derivatives: synthesis, leishmanicidaeffectiveness, and molecular dockingstudies [J]. Medicina...

Claims

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Application Information

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IPC IPC(8): C07D403/12
CPCC07D403/12
Inventor 康从民刘益州王新颖焦林如
Owner QINGDAO UNIV OF SCI & TECH
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