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Preparation method of condensed benzimidazole azetidinone derivative and application of derivative in anti-tumor drug

A technology of azetidinone and anti-tumor drugs, which is applied in the field of benzimidazole azetidinone derivatives and their application in anti-tumor drugs, can solve the problems that new structural compounds have not been reported, and achieve cost Low cost, short synthetic route, and simple operation process

Active Publication Date: 2017-09-08
CHONGQING UNIV OF ARTS & SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although a lot of research on the structure of azetidinone has been carried out, there are no reports of new structural compounds that combine the structures of benzimidazole and azetidinone, and people's attention and research are urgently needed

Method used

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  • Preparation method of condensed benzimidazole azetidinone derivative and application of derivative in anti-tumor drug
  • Preparation method of condensed benzimidazole azetidinone derivative and application of derivative in anti-tumor drug
  • Preparation method of condensed benzimidazole azetidinone derivative and application of derivative in anti-tumor drug

Examples

Experimental program
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Effect test

Embodiment 1

[0042] where R 1 is an alkyl group, R 2 For a hydrogen atom, namely ethyl 2-(1 H -Synthesis of ethyl benzimidazol-2-yl)-1-(2-bromobenzyl)-4-oxoazetidine-2-carboxylate, the specific steps are as follows:

[0043] In a 10-mL microwave reaction tube, ethyl glyoxylate (1.5 mmol) and 2-bromobenzylamine (1.0 mmol) were first dissolved in 2.0 mL of methanol solution, followed by bromoacetic acid (1.0 mol) and isocyanide (1.0 mmol) were added to the solution in turn, the reaction solution was stirred overnight at room temperature, and then the isocyanate was detected by thin-layer chromatography. If there was no remaining isocyanide raw material, the solution was dried with nitrogen, and then Dissolve it with 5.0 ml of dimethylformamide (DMF), then add diisopropylamine (DIPA) (2.0 mmol), and place in a microwave oven at 90 o C for 10 minutes. The solution was diluted with ethyl acetate (15 ml), and washed three times with 20 ml of saturated brine. After the organic phase was drie...

Embodiment 2

[0046] where R 1 is an alkyl group, R 2 For a hydrogen atom, namely ethyl 2-(1 H -Benzimidazol-2-yl)-1-benzyl-4-oxoazetidine-2-carboxylic acid ethyl ester, the specific steps are as follows:

[0047] In a 10 mL microwave reaction tube, ethyl glyoxylate (1.5 mmol) and benzylamine (1.0 mmol) were first dissolved in 2.0 mL of methanol solution, followed by bromoacetic acid (1.0 mmol) and Isocyanides (1.0 mmol) were added to the solution in turn, the reaction solution was stirred overnight at room temperature, and then the isocyanides were detected by thin-layer chromatography. If there were no remaining isocyanides, the solution was dried with nitrogen, and then 5.0 mL of dimethylformamide (DMF) was dissolved, then diisopropylamine (DIPA) (2.0 mmol) was added, and the microwave oven was heated at 90 o C for 10 minutes. The solution was diluted with ethyl acetate (15 ml), and washed three times with 20 ml of saturated brine. After the organic phase was dried with magnesium su...

Embodiment 3

[0050] where R 1 is an alkyl group, R 2 For a hydrogen atom, namely ethyl 2-(1 H - Synthesis of ethyl benzimidazol-2-yl)-1-(3-fluorobenzyl)-4-oxoazetidine-2-carboxylate, the specific steps are as follows:

[0051] In a 10-mL microwave reaction tube, ethyl glyoxylate (1.5 mmol) and 3-fluorobenzylamine (1.0 mmol) were first dissolved in 2.0 mL of methanol solution, and then bromoacetic acid (1.0 mol) and isocyanide (1.0 mmol) were added to the solution in turn, the reaction solution was stirred overnight at room temperature, and then the isocyanate was detected by thin-layer chromatography. If there was no remaining isocyanide raw material, the solution was dried with nitrogen, and then Dissolve it with 5.0 ml of dimethylformamide (DMF), then add diisopropylamine (DIPA) (2.0 mmol), and place in a microwave oven at 90 o C for 10 minutes. The solution was diluted with ethyl acetate (15 ml), and washed three times with 20 ml of saturated brine. After the organic phase was drie...

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Abstract

The invention relates to a preparation method and application of a condensed benzimidazole azetidinone derivative. The method comprises the steps of performing ring closure into azetidinone under an alkaline condition based on a Ugi reaction, and then obtaining a benzimidazole ring under an acidic condition. The condensed benzimidazole azetidinone derivative has potential anti-tumor activity.

Description

technical field [0001] The application relates to the field of medicine, especially a class of condensed benzimidazole azetidinone derivatives and their application in antitumor drugs. Background technique [0002] Benzimidazole compounds have a wide range of biological activities, and are used in anti-tumor, anti-inflammatory and other diseases, and can also be used as important intermediates in organic reactions. In today's advocacy of green chemistry, how to further green the synthesis of benzimidazole compounds is still an important issue. [0003] Azetidinone compounds are also important drug groups, which are reflected in many drugs. The first and only selective cholesterol absorption inhibitor Ezetimibe (Ezetimibe) is a major innovation in lipid-lowering drugs in the past 15 years. The drug is azetidinone compound. Although a lot of studies on the structure of azetidinone have been carried out, there is no report of a new structure compound combining the structures ...

Claims

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Application Information

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IPC IPC(8): C07D403/04A61P35/00
CPCC07D403/04
Inventor 陈中祝徐志刚
Owner CHONGQING UNIV OF ARTS & SCI
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