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A quinoxaline azetidinone compound and its application in antitumor

A technology of azetidinone and quinoxaline, applied to quinoxaline and azetidinone compounds and their application fields in antitumor drugs, can solve problems such as unreported, achieve short synthetic route, The effect of easy availability of raw materials and simple operation process

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 studies on the azetidinone structure have been carried out, there are no reports of new structural compounds of the common combination of the quinoxaline and azetidinone structures, which are in urgent need of people's attention and research

Method used

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  • A quinoxaline azetidinone compound and its application in antitumor
  • A quinoxaline azetidinone compound and its application in antitumor
  • A quinoxaline azetidinone compound and its application in antitumor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] where R 1 is a hydrogen atom, R 2 is a hydrogen atom, R 3 is benzyl, that is, N-benzyl-1-oxo-3-phenyl-1,2-dihydro-2aH-azetidine[1,2-a]quinoxaline-2a-carboxamide Synthesis, the specific steps are as follows:

[0040] In a 10-mL microwave reaction tube, phenylglyoxal (1.0 mmol) and Boc-protected anthraniline (1.0 mmol) were dissolved in 2.0 mL of methanol solution, and then bromoacetic acid (1.0 mol) and benzyl 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 isocyanine raw material, the solution was blown dry with nitrogen , and then dissolved in 5.0 ml of dimethylformamide (DMF), then added diisopropylamine (DIPA) (2.0 mmol), 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...

Embodiment 2

[0043] where R 1 is a hydrogen atom, R 2 is a hydrogen atom, R 3 is an alkyl group, that is, N-cyclohexyl-1-oxo-3-phenyl-1,2-dihydro-2aH-azetidine[1,2-a]quinoxaline-2a-carboxamide Synthesis, the specific steps are as follows:

[0044] In a 10-mL microwave reaction tube, phenylglyoxal (1.0 mmol) and Boc-protected anthraniline (1.0 mmol) were dissolved in 2.0 mL of methanol solution, and then bromoacetic acid (1.0 mol) and cyclohexane isocyanate (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 isocyanate raw material, the solution was blown with nitrogen dry, and then dissolved with 5.0 ml of dimethylformamide (DMF), then added diisopropylamine (DIPA) (2.0 mmol), 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...

Embodiment 3

[0047] where R 1 is methoxy, R 2 is a hydrogen atom, R 3 For benzyl, namely N-benzyl-3-(4-methoxyphenyl)-1-oxo-1,2-dihydro-2aH-azetidine[1,2-a]quinoxa The synthesis of phenoline-2a-carboxamide, concrete steps are as follows:

[0048] In a 10 mL microwave reaction tube, first dissolve p-methoxybenzaldehyde (1.0 mmol) and Boc-protected anthraniline (1.0 mmol) in 2.0 mL of methanol solution, and then add bromine Acetic acid (1.0 mmol) and benzyl isocyanate (1.0 mmol) were successively added to the solution, the reaction solution was stirred overnight at room temperature, and then thin-layer chromatography was used to detect the isocyanate. If there was no remaining isocyanate raw material, the solution Blow dry with nitrogen, then dissolve with 5.0 ml of dimethylformamide (DMF), 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 ...

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Abstract

The invention relates to an quinoxaline-azetidinones compound preparation and an application of the quinoxaline-azetidinones compound in tumor resistance. According to the invention, a Ugi reaction is taken as a base, under microwave assistance, azetidinone is obtained through ring closure under diisopropylamine condition, then quinoxaline ring is obtained in a trifluoroacetic acid / dichloroethanes solution with concentration of 10%, and the quinoxaline-azetidinones compound has latent antitumor activity.

Description

technical field [0001] The application relates to the field of medicine, specifically a class of quinoxaline azetidinone compounds and their application in antitumor drugs. Background technique [0002] Quinoxaline derivatives are important drug intermediates and therefore have a wide range of biological activities. It can be used as an antitumor drug, HIV-1 reverse transcriptase inhibitor, NMDA receptor antagonist and the like. Studies in recent years have shown that quinoxaline reducing drugs have hypoxia-selective cytotoxicity, can be reduced and activated by biological enzymes under hypoxic conditions, selectively kill tumor hypoxic cells, and become effective anti-tumor sensitizers. agents, many of which have entered clinical research. [0003] The structure of azetidinones is also an important active group of drugs. The most typical one is Ezetimibe (Ezetimibe) lipid-lowering drug. Research on this basis has always attracted much attention, and many of them have ente...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61P35/00
CPCC07D487/04
Inventor 陈中祝徐志刚
Owner CHONGQING UNIV OF ARTS & SCI
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