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Synthetic method of 4-hydroxyquinolinone derivative and application in anti-tumor research

A technology for hydroxyquinolinone and derivatives, which is applied in the field of synthesis of 4-hydroxyquinolinone derivatives, can solve problems such as unreported new structure compounds of 4-hydroxyquinolinone, and achieves low cost and simple operation process. , the effect of short synthetic route

Active Publication Date: 2017-12-05
CHONGQING UNIV OF ARTS & SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Though, quinolinone structure has a lot of researches to carry out, the 4-hydroxyquinolinone new structure compound that the present invention relates to has not yet reported, urgently needs people's attention and research

Method used

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  • Synthetic method of 4-hydroxyquinolinone derivative and application in anti-tumor research
  • Synthetic method of 4-hydroxyquinolinone derivative and application in anti-tumor research
  • Synthetic method of 4-hydroxyquinolinone derivative and application in anti-tumor research

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] where R 1 is an alkyl group, R 2 is an aryl group, that is N -Synthesis of benzyl-4-hydroxyl-2-(4-methoxyphenyl)-1-oxo-1,2-dihydroisoquinoline-3-carboxamide, the specific steps are as follows:

[0045] In a 10-mL microwave reaction tube, ethyl glyoxylate (1.5 mmol) and methoxyaniline (1.0 mmol) were dissolved in 2.0 mL of methanol solution, followed by monomethyl phthalate Ester (1.0 mmol) and benzyl isocyanide (1.0 mmol) were sequentially added to the solution, 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 used Blow dry with nitrogen, then dissolve with 5.0 ml of dimethylformamide (DMF), then add 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU) (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 or...

Embodiment 2

[0048] where R 1 is an alkyl group, R 2 is an aryl group, that is N -Synthesis of benzyl-2-(4-bromophenyl)-4-hydroxyl-1-oxo-1,2-dihydroisoquinoline-3-carboxamide, the specific steps are as follows:

[0049] In a 10 mL microwave reaction tube, first dissolve ethyl glyoxylate (1.5 mmol) and 4-bromoaniline (1.0 mmol) in 2.0 mL of methanol solution, and then add phthalate monomethyl Ester (1.0 mmol) and benzyl isocyanide (1.0 mmol) were sequentially added to the solution, 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 used Blow dry with nitrogen, then dissolve with 5.0 ml of dimethylformamide (DMF), then add 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU) (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 org...

Embodiment 3

[0052] where R 1 is an alkyl group, R 2 is an alkyl group, that is, 4-hydroxy-2-isobutyl-1-oxo- N -Synthesis of phenethyl-1,2-dihydroisoquinoline-3-formamide, the specific steps are as follows:

[0053] In a 10 mL microwave reaction tube, first dissolve ethyl glyoxylate (1.5 mmol) and 2-isobutylamine (1.0 mmol) in 2.0 mL of methanol solution, and then add phthalic acid Monomethyl ester (1.0 mmol) and phenylethyl isocyanide (1.0 mmol) were sequentially added to the solution, 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 materials, the solution was blown dry with nitrogen, then dissolved in 5.0 ml of dimethylformamide (DMF), and then added 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU) ( 2.0 mmol), 90 in the microwave 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 o...

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Abstract

The invention relates to a preparation method and application of a 4-hydroxyquinolinone derivative. Based on Ugi reaction and under the alkaline condition, a quinolinone compound is formed through ring closing. The 4-hydroxyquinolinone derivative has latent anti-tumor activity.

Description

technical field [0001] This application relates to the field of drug synthesis, especially the synthesis method of 4-hydroxyquinolinone derivatives and their application in antitumor research. Background technique [0002] After nearly 50 years of research and development, quinolinone derivatives have been widely used in clinical research as broad-spectrum, high-efficiency, low-toxicity anti-tumor inhibitors. It has been found through research that the targets of this kind of quinolinone derivatives on tumor cells include topoisomerase I, microprotein, CK2 protein kinase receptor and JAK-STAT3 signal transduction pathway in addition to topoisomerase II. Wait. [0003] Although quinoline exists in coal tar, its content is not much. Quinolinone and its derivatives are generally synthesized by ring-closure of benzene derivatives. In addition to some classic synthetic methods, the common synthetic methods of quinolinone and its derivatives in recent years are: microwave radiat...

Claims

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Application Information

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IPC IPC(8): C07D217/26A61P35/00
CPCC07D217/26
Inventor 徐志刚陈中祝
Owner CHONGQING UNIV OF ARTS & SCI
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