Preparation of 13 (18)-oleanane-type pentacyclic triterpene and derivatives of 13(18)-oleanane-type pentacyclic triterpene

A technology for oleanane and pentacyclic triterpenes, applied in the field of pharmacy, can solve problems such as limited plant sources, and achieve the effects of low price, little environmental pollution and high yield

Inactive Publication Date: 2011-05-11
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far there is no semi-synthetic method of 13(18)-ene oleanane type pentacycli

Method used

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  • Preparation of 13 (18)-oleanane-type pentacyclic triterpene and derivatives of 13(18)-oleanane-type pentacyclic triterpene
  • Preparation of 13 (18)-oleanane-type pentacyclic triterpene and derivatives of 13(18)-oleanane-type pentacyclic triterpene
  • Preparation of 13 (18)-oleanane-type pentacyclic triterpene and derivatives of 13(18)-oleanane-type pentacyclic triterpene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of 3β-hydroxy-13(18)-eneoleanolic acid-28-benzyl ester

[0038]

[0039] Add 8 grams of 3β-hydroxy-12-ene oleanolic acid-28-benzyl ester, 10 milliliters of trifluoroacetic acid, and 40 milliliters of dichloromethane to the reaction flask in sequence, and stir at room temperature for 4 hours. No obvious raw material residue is detected by TLC. , evaporated to remove the organic solvent, and obtained 3β-hydroxy-13(18)-ene oleanolic acid-28-benzyl ester by column chromatography.

[0040] 1 H NMR (CDCl 3 , 300M) δ0.74(3H, s), 0.78(3H, s), 0.81(3H, s), 0.87(3H, s), 0.88(3H, s), 0.99(3H, s), 1.15(3H , s), 0.72-1.95 (21H, m), 2.19-2.23 (1H, m), 2.42 (1H, d, J=14.2Hz), 2.73-2.77 (1H, m), 3.21-3.26 (1H, m ), 5.10 (1H, d, J = 12.4Hz), 5.16 (1H, d, J = 12.3Hz), 7.35 (5H, brs); 13 C NMR (CDCl 3 , 75M) δ15.5, 16.3, 17.5, 18.3, 21.0, 21.6, 24.2, 25.2, 27.0, 27.3, 28.1, 32.1, 32.6, 33.0, 34.9, 35.8, 36.8, 37.3, 38.8, 41.0, 41.3, 44.4, 48.5 , 50.7, 55.3, 66.2, 79.0...

Embodiment 2

[0042] Preparation of 3β-hydroxy-13(18)-eneoleanolic acid-28-benzyl ester

[0043]

[0044] Dissolve 1.5 ml of concentrated sulfuric acid in acetone, add 97 g of silica gel, stir at room temperature for 3 hours, evaporate the solvent, and obtain a solid acid in which sulfuric acid is adsorbed on silica gel. Add 1 g of 3β-hydroxy-12-ene oleanolic acid-28-benzyl in turn to the reaction flask, 1 g of the solid acid adsorbed on silica gel by the above-mentioned sulfuric acid, and 15 ml of dichloromethane, stir and react at room temperature for 8 hours, and detect by TLC When no obvious raw materials remained, the solid was filtered off, the organic solvent was distilled off, and 3β-hydroxy-13(18)-eneoleanolic acid-28-benzyl ester was obtained by column chromatography.

Embodiment 3

[0046] Preparation of 3β-hydroxy-13(18)-eneoleanolic acid-28-benzyl ester

[0047]

[0048] Add 0.2 g of 3β-hydroxy-12-ene oleanolic acid-28-benzyl ester, 0.26 g of montmorillonite KSF, CH 2 Cl 2 3 ml, heated and stirred to react for 12 hours, TLC detected that there was no obvious raw material residue, filtered with suction, and the filter cake was washed with CH 2 Cl 2 10 ml × 2 washes, and the filtrate was evaporated to dryness to obtain 3β-hydroxy-13(18)-ene oleanolic acid-28-benzyl ester.

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Abstract

The invention relates to the field of pharmacy, in particular to a synthesis method of 13 (18)-oleanane-type pentacyclic triterpene as shown in a formula II and derivatives or pharmaceutically acceptable salts or esters of the 13 (18)-oleanane-type pentacyclic triterpene by 12-oleanane-type pentacyclic triterpene as shown in a formula I and derivatives of the 12-oleanane-type pentacyclic triterpene. Definitions of R1-9 are as shown in specification.

Description

technical field [0001] The invention relates to the field of pharmacy, in particular to the preparation of 13(18)-ene-oleanane-type pentacyclic triterpenes and derivatives thereof from 12-ene-oleanane-type pentacyclic triterpenes and their derivatives or pharmaceutically acceptable Accepted Salt or Ester Preparation Methods. The present invention also provides some novel 13(18)-ene oleanane type pentacyclic triterpenes and their derivatives and their pharmaceutically acceptable salts or esters. Background technique [0002] 12-Oleanane-type pentacyclic triterpenes are important natural products that are widely found in various plants. Many of these compounds have broad and important biological activities. For example, oleanolic acid is an active ingredient of many traditional Chinese medicines, such as Ligustrum lucidum, Acanthopanax, Heart-Yangcao, etc. It is also widely found in health foods, such as hawthorn, olive, papaya, etc. Oleanolic acid and its derivatives have ...

Claims

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Application Information

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IPC IPC(8): C07J63/00
Inventor 孙宏斌张璞郝佳
Owner CHINA PHARM UNIV
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