Anti-cancer activity indole derivative, synthesis method and uses thereof

A technology of indole derivatives and anticancer drugs, applied in the direction of organic active ingredients, drug combinations, medical preparations containing active ingredients, etc., can solve the problem of undiscovered anticancer activity, active targets and substituents of indole derivatives There is no clear understanding and other issues

Active Publication Date: 2015-05-06
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] But so far, people have not found that indole derivatives have anticancer activity, and there is still no clear understanding of their active targets and substituents

Method used

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  • Anti-cancer activity indole derivative, synthesis method and uses thereof
  • Anti-cancer activity indole derivative, synthesis method and uses thereof
  • Anti-cancer activity indole derivative, synthesis method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Example 1: 7-(4-fluorobenzoyl)indole

[0066]

[0067] At room temperature, add 100ml of solvent (a mixture of 2-MeTHF and water, the volume ratio of which is 2:1), 20mmol of 7-cyanindole, 40mmol of p-fluorophenylboronic acid, 1mmol of palladium trifluoroacetate, 1.5 mmol of the above-mentioned ligand L2 and 200 mmol of methanesulfonic acid; the temperature was raised to 80° C. under stirring, and the reaction was kept for 35 hours.

[0068] After the reaction is finished, add 100ml of water to the reaction mixture, extract 2-4 times with ether, combine the ether layers, and dry with anhydrous sodium sulfate, filter, evaporate and remove the ether for concentration, pass the concentrate through a 300-400 mesh silica gel column , using a mixture of ethyl acetate / petroleum ether as the eluent, wherein the volume ratio of ethyl acetate to petroleum ether was 1:10, and the eluate was concentrated to obtain the title compound as a yellow solid, named A. It has a yield of...

Embodiment 2

[0072] Example 2: 7-(4-Chlorobenzoyl)indole

[0073]

[0074] At room temperature, add 100ml of solvent (a mixture of 2-MeTHF and water, the volume ratio of which is 2:1), 20mmol of 7-cyanindole, 20mmol of p-chlorophenylboronic acid, 0.4mmol of palladium trifluoroacetate to the reaction vessel , 1 mmol of the above-mentioned ligand L2 and 100 mmol of methanesulfonic acid; the temperature was raised to 60° C. under stirring, and the reaction was kept for 40 hours.

[0075] After the reaction is finished, add 100ml of water to the reaction mixture, extract 2-4 times with ether, combine the ether layers, and dry with anhydrous sodium sulfate, filter, evaporate and remove the ether for concentration, pass the concentrate through a 300-400 mesh silica gel column , using a mixture of ethyl acetate / petroleum ether as the eluent, wherein the volume ratio of ethyl acetate to petroleum ether was 1:5, and the eluate was concentrated to obtain the title compound as a yellow solid, name...

Embodiment 3

[0079] Example 3: 7-(3,4,5-trimethoxybenzoyl)indole

[0080]

[0081] At room temperature, add 100ml of solvent (a mixture of 2-MeTHF and water, the volume ratio of which is 2:1), 20mmol of 7-cyanindole, 60mmol of 3,4,5-trimethoxyphenylboronic acid, 1.5 mmol of palladium trifluoroacetate, 2 mmol of the above-mentioned ligand L2 and 300 mmol of methanesulfonic acid; the temperature was raised to 100° C. under stirring, and the reaction was kept for 30 hours.

[0082] After the reaction is finished, add 100ml of water to the reaction mixture, extract 2-4 times with ether, combine the ether layers, and dry with anhydrous sodium sulfate, filter, evaporate and remove the ether for concentration, pass the concentrate through a 300-400 mesh silica gel column , using a mixture of ethyl acetate / petroleum ether as the eluent, wherein the volume ratio of ethyl acetate to petroleum ether was 1:15, and the eluate was concentrated to obtain the title compound as a yellow solid, named as ...

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Abstract

The present invention relates to an indole derivative and uses of the indole derivative in preparation of anti-cancer drugs for tumor inhibition, wherein a cyano indole compound and a boric acid compound can be subjected to one-step synthesis in the presence of a catalyst, a ligand and an additive so as to obtain the derivative. According to the present invention, the derivative has the excellent anti-cancer activity, and results of the activity test show that the derivative provides good tumor cell growth inhibition effects on human gastric cancer cell line (SGC-7901), human lung cancer cell line (H446) and human gastric cancer cell line (HGC-27), such that the derivative can be adopted as the anti-tumor drug in the medicine field and has good medical research prospects and industrial application values.

Description

technical field [0001] The invention relates to a pharmaceutically active compound, in particular to an indole derivative with excellent anticancer activity, a synthesis method and its use, and belongs to the field of medicinal chemistry. Background technique [0002] Indole derivatives are an important class of nitrogen-containing and oxygen-containing organic compounds, which play an important role in organic and pharmaceutical synthesis. Therefore, it has attracted much attention in the fields of pharmaceutical chemical industry, organic synthesis and material chemistry. [0003] So far, a variety of pharmaceutical compounds having indole structures have been developed. For example, 7-benzoyl indol-2-one is usually used to synthesize non-steroidal anti-inflammatory analgesic drug Amfenac sodium (amfenac sodium); and 7-(p-bromobenzoyl)indole-2- Ketones are commonly used to synthesize the non-steroidal anti-inflammatory analgesic drug Bromfenac sodium (bromfenac sodium): ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/404A61P35/00C07D209/08
Inventor 陈久喜吴华悦高文霞刘妙昌黄小波
Owner WENZHOU UNIVERSITY
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