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A kind of benzimidazole azetidinone derivative and its application in antitumor drug

A technology for azetidinone and antitumor drugs, which is applied to benzimidazole azetidinone derivatives and their application fields in antitumor drugs, can solve problems such as unreported new structure compounds, and achieve cost The effect of low, simple operation process and short synthesis route

Active Publication Date: 2019-11-05
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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  • A kind of benzimidazole azetidinone derivative and its application in antitumor drug
  • A kind of benzimidazole azetidinone derivative and its application in antitumor drug
  • A kind of benzimidazole azetidinone derivative and its application in antitumor drug

Examples

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Embodiment 1

[0042] where R 1 is an alkyl group, R 2 For the hydrogen atom, that is, the synthesis of 2-(1H-benzimidazol-2-yl)-1-(2-bromobenzyl)-4-oxoazetidine-2-carboxylic acid ethyl ester, specific steps 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, and then bromoacetic acid (1.0 mol) and isocyanide (1.0 mmol) were added in this solution successively, and the reaction solution was stirred overnight at room temperature, and then the isocyanate was detected by thin-layer chromatography. If there was no remaining isocyanine 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 react in a microwave oven at 90° C. for 10 minutes. The solution was diluted with ethyl acetate (15 mL), and washed three times with saturated brine, 20 mL each time. After the organi...

Embodiment 2

[0046] where R 1 is an alkyl group, R 2For the synthesis of hydrogen atom, i.e. 2-(1H-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, and then bromoacetic acid (1.0 mmol) and Isocyanides (1.0 mmol) were sequentially added to the solution, and the reaction solution was stirred overnight at room temperature, and then the isocyanides were detected by thin-layer chromatography. If there was no remaining isocyanide raw material, the solution was dried with nitrogen, and then 5.0 A milliliter of dimethylformamide (DMF) was dissolved, and then diisopropylamine (DIPA) (2.0 mmol) was added, and reacted in a microwave oven at 90° C. for 10 minutes. The solution was diluted with ethyl acetate (15 mL), and washed three times with saturated brine, 20 mL each time. After the or...

Embodiment 3

[0050] where R 1 is an alkyl group, R 2 For the hydrogen atom, that is, the synthesis of 2-(1H-benzimidazol-2-yl)-1-(3-fluorobenzyl)-4-oxoazetidine-2-carboxylic acid ethyl ester, specific steps 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 in this solution successively, and the reaction solution was stirred overnight at room temperature, and then the isocyanate was detected by thin-layer chromatography. If there was no remaining isocyanine 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 react in a microwave oven at 90° C. for 10 minutes. The solution was diluted with ethyl acetate (15 mL), and washed three times with saturated brine, 20 mL each time. After the orga...

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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 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 of benzimi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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