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A kind of synthetic method and antitumor application of indazole derivatives

A technology of derivatives and indazoles, which is applied in the field of rapid preparation of indazole derivatives, and achieves the effects of simple operation process, strong inhibitory effect and short synthetic route

Active Publication Date: 2020-03-20
CHONGQING UNIV OF ARTS & SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are not many reports on the compounds constructed by indazole derivatives through multi-component reactions, and more attention and research are urgently needed

Method used

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  • A kind of synthetic method and antitumor application of indazole derivatives
  • A kind of synthetic method and antitumor application of indazole derivatives
  • A kind of synthetic method and antitumor application of indazole derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0043] where R 1 is benzyl, R 2 is aryl, R 3 Synthesis of N, 1,4-dibenzyl-1-oxo-2-phenyl-1,2-dihydropyrazino[1,2-b]indazole-3-carboxamide ,Specific steps are as follows:

[0044] In a 5 mL microwave reaction tube, dissolve 1.0 mmol of 3-phenylpropargylaldehyde in 2 mL of trifluoroethanol, add 1.0 mmol of aniline, stir at room temperature for 10 minutes, and then add 1.0 mmol of 1H-indazole-3-carboxylate acid and 1.0 mmol benzyl isonitrile, stirred overnight at room temperature. TLC detection reaction. After the reaction was complete, the solvent was removed, the residue was dissolved in DMF (5.0 mL), and placed in a microwave reactor for 110 oC for 20 minutes. After the reaction was completed, it was cooled to room temperature, the reaction solution was poured into 15 mL ethyl acetate, washed with saturated brine, the organic phase was dried over anhydrous magnesium sulfate, concentrated, and separated by gradient elution with ethyl acetate / n-hexane (0-60%) to obtain Th...

Embodiment 2

[0047] where R 1 is benzyl, R 2 is aryl, R 3 is a hydrogen atom, namely N,1,4-dibenzyl-2-(4-methoxyphenyl)-1-oxo-1,2-dihydropyrazino[1,2-b]indazole The synthesis of -3-carboxamide, concrete steps are as follows:

[0048] In a 5 mL microwave reaction tube, dissolve 1.0 mmol of 3-phenylpropargylaldehyde in 2 mL of trifluoroethanol, add 1.0 mmol of p-methoxyaniline, stir at room temperature for 10 minutes, and then add 1.0 mmol of 1H-indole Azole-3-carboxylic acid and 1.0 mmol benzyl isonitrile were stirred overnight at room temperature. TLC detection reaction. After the reaction was completed, the solvent was removed, the residue was dissolved in DMF (5.0 mL), and placed in a microwave reactor for 110 o C for 20 minutes. After the reaction was completed, it was cooled to room temperature, the reaction solution was poured into 15 mL ethyl acetate, washed with saturated brine, the organic phase was dried over anhydrous magnesium sulfate, concentrated, and separated by gradie...

Embodiment 3

[0051] where R 1 is phenethyl, R 2 is aryl, R 3 is a hydrogen atom, namely 4-benzyl-1-oxo-N-phenethyl-2-phenyl-1,2-dihydropyrazino[1,2-b]indazole-3-carboxamide Synthesis, the specific steps are as follows:

[0052] In a 5 mL microwave reaction tube, dissolve 1.0 mmol of 3-phenylpropargylaldehyde in 2 mL of trifluoroethanol, add 1.0 mmol of aniline, stir at room temperature for 10 minutes, and then add 1.0 mmol of 1H-indazole-3- Carboxylic acid and 1.0 mmol phenethylisonitrile were stirred overnight at room temperature. TLC detection reaction. After the reaction was complete, the solvent was removed, the residue was dissolved in DMF (5.0 mL), and placed in a microwave reactor for 110 o C for 20 minutes. After the reaction was completed, it was cooled to room temperature, the reaction solution was poured into 15 mL ethyl acetate, washed with saturated brine, the organic phase was dried over anhydrous magnesium sulfate, concentrated, and separated by gradient elution with e...

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Abstract

The invention relates to a preparation method and application of carbazole derivatives. On the basis of a four-component Ugi reaction, the carbazole derivatives are synthesized through cyclization ofsynthesized intermediates by a microwave assisted reaction in a DMF (dimethyl formamide) solvent on the basis of no purification. The carbazole derivatives have antitumor activity.

Description

technical field [0001] The application relates to the field of drug synthesis, especially a rapid preparation method of indazole derivatives and its application in antitumor drugs. Background technique [0002] Indazole derivatives are a very important class of pharmacologically active compounds. It has biological activities such as anti-tumor, anti-virus, anti-bacteria and anti-microbial, and some indazole derivatives can be used as inhibitors of CDK7 for the study of tumor activity, and have remarkable efficacy. CDK7 is an important member of the CDKs family, which has dual functions of activating CDK1, 2, 3, 4 and 6 and regulating the transcription process. By inhibiting the activity of CDK7, the proliferation of tumor cells can be effectively inhibited. Therefore, it is of great significance to develop new CDK7 inhibitors. [0003] There are many methods for the synthesis of indazole derivatives, among which the cyclization reaction of aromatic ketone phenylhydrazone i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61P35/00
CPCA61P35/00C07D487/04
Inventor 徐志刚陈中祝张亚军
Owner CHONGQING UNIV OF ARTS & SCI
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