Novel oleanolic acid derivatives, and preparation method and application thereof

A technology of oleanolic acid and derivatives, applied in the field of new oleanolic acid derivatives, can solve the problems of low water solubility and low bioavailability

Inactive Publication Date: 2015-08-26
上海兰蒂斯生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, oleanolic acid itself has low water solubility and low bioavailability

Method used

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  • Novel oleanolic acid derivatives, and preparation method and application thereof
  • Novel oleanolic acid derivatives, and preparation method and application thereof
  • Novel oleanolic acid derivatives, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Embodiment 1: the preparation of compound 1

[0062]

[0063] Suspend 2g of oleanolic acid in 20ml of toluene solution, add 1 equivalent of DPPA (diphenylphosphoryl azide) and 1 equivalent of triethylamine, under nitrogen flow environment, reflux for 3 hours, down to room temperature, the reaction solution with Wash once with 20 ml of saturated potassium carbonate, once with 20 ml of saturated citric acid solution, dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to obtain 1.5 g of compound 1. LC-Ms: ESI: (M+H) 457.2. 1 H NMR (400MHz, CDCl 3 )δ5.28(t, 1H), 3.24(dd, 1H), 2.39(d, 1H), 2.05(d, 1H), 1.91(m4H), 1.69-1.53(m, 7H), 1.52-1.20(m , 6H), 1.16(s, 3H), 1.08-1.10(m, 1H), 1.04(s, 1H), 1.00(s, 3H), 0.96(d, J=4.4Hz, 1H), 0.93(s, 3H), 0.89(s, 3H), 0.87(s, 3H), 0.83(s, 3H), 0.79(s, 3H), 0.70(d, J=8Hz, 1H).

Embodiment 2

[0064] Embodiment 2: Preparation of OA-1

[0065]

[0066] Dissolve isocyanate in dichloromethane, add 3 equivalents of trifluoroacetic acid, react at room temperature for 3 hours, and concentrate the reaction solution to obtain compound 2 (OA-1). LC-Ms: ESI: (M+H) 428.2. 1 H NMR (400MHz, CDCl 3)δ5.25(t, 1H), 3.28(dd1H), 2.42(d, 1H), 2.10(d, 1H), 1.92(m4H), 1.70-1.54(m, 7H), 1.50-1.20(m, 6H ), 1.18(s, 3H), 1.07-1.09(m, 1H), 1.05(s, 1H), 1.01(s, 3H), 0.96(d1H), 0.93(s, 3H), 0.90(s, 3H) , 0.88(s, 3H), 0.83(s, 3H), 0.81(s, 3H), 0.76(d, J=8Hz, 1H).

Embodiment 3

[0067] Embodiment 3: Preparation of OA-2

[0068]

[0069] Suspend the trifluoroacetic acid salt of compound 2 in dichloromethane, add 2 equivalents of triethylamine dropwise at 0°C, and then add 1.5 equivalents of acetyl chloride dichloromethane solution dropwise at this temperature, and raise the temperature to React at 20°C for 3 hours. The reaction solution was washed with water, dried, concentrated under reduced pressure, and purified by column chromatography to obtain compound 3 (OA-2). LC-Ms: ESI: (M+H) 470.2. 1 H NMR (400MHz, CDCl 3 ( m, 7H), 1.50-1.25(m, 6H), 1.16(s, 3H), 1.06-1.04(m, 1H), 1.03(s, 1H), 1.01(s, 3H), 0.95(d, J= 4.0Hz, 1H), 0.93(s, 3H), 0.89(s, 3H), 0.87(s, 3H), 0.81(s, 3H), 0.77(s, 3H), 0.74(d, 1H).

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Abstract

The invention relates to novel oleanolic acid derivatives, and a preparation method and an application thereof. The compounds are modification compounds of 3-site and 28-site substitutes in an oleanolic acid structural formula, are prepared with oleanolic acid as a raw material and by a chemical synthesis method, and can be used for treatment of cancer, diabetes, AIDS, hepatitis B and hepatitis C.

Description

technical field [0001] The invention discloses a novel oleanolic acid derivative, its preparation method and application. Background technique [0002] Oleanolic acid (OA) mainly has the functions of protecting the liver and reducing enzymes, promoting liver cell regeneration, anti-inflammation, anti-oxidation, strengthening the heart, diuresis, anti-tumor, etc. It also has the effects of lowering blood sugar, blood fat, and sedation. It is an active ingredient in the development of drugs for treating liver diseases and lowering blood sugar. However, oleanolic acid itself has low water solubility and low bioavailability. The present invention synthesizes a series of novel oleanolic acid derivatives from cheap and easy-to-get oleanolic acid as a raw material, and provides an effective method for synthesizing novel oleanolic acid derivatives, which can be represented by the following general formula: [0003] Formula 1: [0004] [0005] Formula 2: [0006] [0007] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/56A61K31/58A61P35/00A61P3/10A61P31/18A61P31/20A61P31/14A61P35/02
CPCC07J63/008A61K31/56A61K31/58
Inventor 栾德刚黄文武栾松平肖智俊
Owner 上海兰蒂斯生物医药科技有限公司
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