Preparation method of anti-tumor indole compound, indole compound and application

A compound and indole technology, applied in the field of chemical synthesis, can solve the problems of difficult preparation, high toxicity and side effects, and low drug efficacy, and achieve the effects of environmental friendliness, low toxicity and side effects, and simple and practical operation

Active Publication Date: 2020-02-18
HKUST SHENZHEN RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to provide a preparation method of anti-tumor indole compounds, aiming to solve the technical problems of existing anti-tumor drugs such as high difficulty in preparation, low drug efficacy and great toxicity and side effects.

Method used

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  • Preparation method of anti-tumor indole compound, indole compound and application
  • Preparation method of anti-tumor indole compound, indole compound and application
  • Preparation method of anti-tumor indole compound, indole compound and application

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preparation example Construction

[0037] The embodiment of the present invention provides a preparation method of an anti-tumor indole compound, comprising the following preparation steps:

[0038] Obtain the compound of formula II and the compound of formula III, dissolve the compound of formula II and the compound of formula III in an organic solvent, carry out the synthesis reaction under the condition that the temperature is 0°C to 40°C, and the catalyst is chiral phosphoric acid, to obtain the compound of formula I anti-tumor indole compounds;

[0039] Ar 3 H, formula III;

[0040] Among them, R 1 and R 2 Any one independently selected from alkyl, aryl, heteroaryl, substituted aryl and substituted heteroaryl, Ar 1 、Ar 2 and Ar 3 are independently selected from any one of aryl, heteroaryl, substituted aryl and substituted heteroaryl, and Ar 1 、Ar 2 and Ar 3 different from each other.

[0041] The preparation method of the anti-tumor indole compound provided by the embodiment of the present in...

Embodiment 1

[0070] An indole compound Ia, Including the following preparation steps:

[0071] At room temperature, the R 1 for hydrogen, R 2 is phenyl, Ar 2 is 2-methoxyphenyl, Ar 3 Triarylmethanol (81.3mg, 0.2mmol) and pyrrole (26.8mg, 0.4mmol), which are phenyl groups, were dissolved in dichloromethane (1.6mL), and dichloromethane (14.9mg, 0.015mmol) of chiral phosphoric acid (14.9mg, 0.015mmol) was slowly added dropwise. Methane (0.4 mL) solution was stirred at room temperature for 24 hours, and the reaction solution was directly separated by silica gel column chromatography to obtain Compound Ia, 87.0 mg of white foamy solid, with a calculated yield of 96%.

[0072] In order to further verify that the compound obtained is indeed the target product to be prepared in this embodiment, the obtained product is qualitatively analyzed by measuring the specific rotation, high performance liquid chromatography analysis, ee value, and nuclear magnetic resonance. The analysis of the test is...

Embodiment 2

[0082] A kind of indole compound Ib, Including the following preparation steps:

[0083] At room temperature, the R 1 for hydrogen, R 2 is phenyl, Ar 2 For 2-trifluoromethoxyphenyl, Ar 3 Triarylmethanol (91.9mg, 0.2mmol) and pyrrole (26.8mg, 0.4mmol), which are phenyl groups, were dissolved in dichloromethane (1.6mL), and dichloromethane (14.9mg, 0.015mmol) of chiral phosphoric acid (14.9mg, 0.015mmol) was slowly added dropwise. Methane (0.4 mL) solution was stirred at room temperature for 24 hours, and the reaction solution was directly separated by silica gel column chromatography to obtain compound Ib, 86.5 mg of white foamy solid, and the calculated yield was 85%.

[0084] In order to further verify that the compound obtained is indeed the target product to be prepared in this embodiment, the obtained product is qualitatively analyzed by measuring the specific rotation, high performance liquid chromatography analysis, ee value, and nuclear magnetic resonance. The anal...

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Abstract

The invention belongs to the technical field of chemical synthesis, and particularly relates to a preparation method of an anti-tumor indole compound. The preparation method comprises the following steps: obtaining a compound shown in a formula II and a compound shown in a formula III, dissolving the compound shown in the formula II and the compound shown in the formula III in an organic solvent,and carrying out a synthetic reaction under a condition that the temperature is 0-40 DEG C and a catalyst is chiral phosphoric acid to obtain the anti-tumor indole compound shown in a formula I, wherein R<1> and R<2> are ones separately selected from alkyl, aryl, heteroaryl, substituted aryl and substituted heteroaryl; Ar<1>, Ar<2> and Ar<3> are ones separately selected from aryl, heteroaryl and substituted heteroaryl; and the Ar<1>, the Ar<2> and the Ar<3>differ from each other. The preparation method provided by the invention has the characteristics of simple and practical operation, high yield, greenness and economy, environmental friendliness and easy industrialization. The formula II the formula III and the formula I are represented as in the description.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to an indole compound, a preparation method of an anti-tumor indole compound, and a tumor suppressor. Background technique [0002] With the continuous improvement of social development and human living standards, people pay more and more attention to health problems. As one of the deadliest diseases in the world, cancer remains the most serious challenge to human health. For the treatment of cancer, drug therapy, namely chemotherapy, as one of the most commonly used traditional treatment methods in clinical practice, still faces huge problems and challenges. On the one hand, the drug molecules used in chemotherapy need to be able to efficiently act on cancer cells or pathogenic microorganisms, and kill a large proportion of cancer cells by interacting with them; Cells can also cause greater damage to normal cells. In addition, the preparation of anticancer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/06C07D409/14A61K31/404A61P35/00
CPCC07D403/06C07D409/14A61P35/00C07B2200/07
Inventor 孙建伟李星光
Owner HKUST SHENZHEN RES INST
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