18 beta-glycyrrhetinic acid derivative and application thereof

A kind of derivative, propionic acid technology, applied in the field of medicine, can solve the problem of not meeting clinical needs and so on

Active Publication Date: 2017-09-01
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional chemotherapy drugs are far from meeting clinical needs

Method used

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  • 18 beta-glycyrrhetinic acid derivative and application thereof
  • 18 beta-glycyrrhetinic acid derivative and application thereof
  • 18 beta-glycyrrhetinic acid derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] Example 1: 3-(1-(2-((11-oxo-18β-oleanane-12-ene-30-methyl carboxylate)-3β-oxo)-2-oxoethyl) Preparation of -1H-benzimidazol-2-yl)propionic acid

[0081] Step A:

[0082]

[0083] Glycyrrhetinic acid methyl ester (2.00g, 4.13mmol) was dissolved in 70mL dry dichloromethane, triethylamine (2.00mL) was added, 2-chloroacetyl chloride (2.00mL, 25.36mmol) was added dropwise under ice-cooling, room temperature The reaction was monitored by TLC. After the reaction was completed, water was added to quench, the organic phase was separated, and the aqueous phase was extracted 3 times with dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, and purified by column chromatography. The yield is about 68%.

[0084] Step B:

[0085]

[0086] Put o-phenylenediamine (5.00g, 46mmol) in a 250mL eggplant-shaped bottle, add 110mL of dioxane at room temperature, stir and dissolve, then add succinic anhydride (5.55g, 55.5mmol). Transfer to an oil ba...

Embodiment 2

[0096] Example 2: 3-(1-(2-((18β-Oleanane-12-ene-30-carboxylic acid methyl ester)-3β-oxygen)-2-oxoethyl)-1H-benzo Preparation of imidazol-2-yl)propionic acid

[0097] According to the preparation method of Example 1, the title compound was prepared.

Embodiment 3

[0098] Example 3: 3-(1-(2-((12-oxo-18β-oleanane-30-carboxylic acid methyl ester)-3β-oxygen)-2-oxoethyl)-1H-benzene Preparation of imidazol-2-yl)propionic acid

[0099] According to the preparation method of Example 1, the title compound was prepared.

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PUM

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Abstract

The invention relates to the technical field of medicines, in particular to an 18 beta-glycyrrhetinic acid derivative with Pin1 inhibitory activity and pharmacologically-acceptable salt thereof, a preparation method of the derivative, a pharmaceutical composition taking the derivative as an active ingredient and application of the derivative to the preparation of a Pin1 inhibitor and the preparation of a drug for treating and / or preventing various cancers. The derivative shown in a general formula I or the pharmacologically-acceptable salt thereof has the following structure, wherein R, X, Y and n are stated in the claims and the descriptions.

Description

[0001] Technical field: [0002] The present invention belongs to the technical field of medicine, and specifically relates to 18β-glycyrrhetinic acid derivatives with Pin1 inhibitory activity and pharmaceutically acceptable salts thereof, a preparation method of such derivatives, and a pharmaceutical composition using the derivatives as active ingredients. As well as the use in the preparation of Pin1 inhibitors for the preparation of medicines for treating and / or preventing various cancers. [0003] Background technique: [0004] Malignant tumors seriously endanger human health, and their morbidity and mortality continue to increase. Among the many cancer treatment methods, chemotherapy is still one of the effective methods for treating tumors. Traditional chemotherapy drugs are far from meeting clinical needs. In recent years, breakthroughs have been made in the research of anti-tumor targeted drugs, which has alleviated the pain of cancer patients in the course of disease...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/58A61P35/00
CPCC07J63/008
Inventor 赵临襄刘丹李坤马天一景永奎
Owner SHENYANG PHARMA UNIVERSITY
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