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Quinoxaline-azetidinones compound preparation and application of quinoxaline-azetidinones compound in tumor resistance

A technology of azetidinone and quinoxaline, which is applied in the field of quinoxaline azetidinone compounds and their application in antitumor drugs, can solve the problems that have not been reported, and achieve short synthetic routes, The effect of simple operation process and low cost

Active Publication Date: 2017-11-17
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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  • Quinoxaline-azetidinones compound preparation and application of quinoxaline-azetidinones compound in tumor resistance
  • Quinoxaline-azetidinones compound preparation and application of quinoxaline-azetidinones compound in tumor resistance
  • Quinoxaline-azetidinones compound preparation and application of quinoxaline-azetidinones compound in tumor resistance

Examples

Experimental program
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Effect test

Embodiment 1

[0039] where R 1 is a hydrogen atom, R 2 is a hydrogen atom, R 3 is an alkyl group, that is N -Benzyl-1-oxo-3-phenyl-1,2-dihydro-2 aH -Methyl[1,2- a ]quinoxaline-2 a -The synthesis of formamide, concrete 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, followed by 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), 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 orga...

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-2 HH -Methyl[1,2- a ]quinoxaline-2 a -The synthesis of formamide, concrete 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, followed by bromoacetic acid (1.0 mol) and cyclohexane 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 with nitrogen Dry, then redissolve with 5.0 mL of dimethylformamide (DMF), then add diisopropylamine (DIPA) (2.0 mmol), 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 ...

Embodiment 3

[0047] where R 1 is methoxy, R 2 is a hydrogen atom, R 3 is an alkyl group, that is N -Benzyl-3-(4-methoxyphenyl)-1-oxo-1,2-dihydro-2 HH -Methyl[1,2- a ]quinoxaline-2 a -The synthesis of formamide, concrete steps are as follows:

[0048] In a 10-mL microwave reaction tube, first dissolve p-methoxybenzoylglyoxal (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 isocyanide (1.0 mmol) were sequentially added to the solution, 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 isocyanate, the solution Blow dry with nitrogen, then dissolve with 5.0 ml of dimethylformamide (DMF), then add diisopropylamine (DIPA) (2.0 mmol), 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. Aft...

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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. The research on this basis has always attracted much attention, and many of them have ...

Claims

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Application Information

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Patent Type & Authority Applications(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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