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Method for preparing composite with antineoplastic activity by panoxadiol

A technology of anti-tumor activity and panaxadiol, which is applied in the field of anti-tumor compounds produced by panaxadiol through side chain opening, can solve the problems of no discovery and no preparation method, and achieve the effect of mild conditions

Active Publication Date: 2009-09-23
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no related preparation method of the above compound at present, and no method for preparing the above compound by panaxadiol has been found

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Add ginseng diol (5g) and 250ml methanol into a sealable container, dissolve it by ultrasonic, add 250ml (1%-37%) HCL, and react ultrasonically at 20-60°C for 0.5-2 hours. The hydrolyzate was analyzed by HPLC, and the PD conversion rate was ≥85%. After the reaction solution was neutralized, it was extracted with ethyl acetate, and the total reaction product was separated through a silica gel (200-300 mesh) column, and the mobile phase was selected as petroleum ether: acetone gradient elution (10:1, 5:1, 3:1 , 1:1), to obtain 20(R)-dammarane-3β,12β,20,25-tetraol (1.3g), 20(R)-25-methoxy-dammarane-3β,12β, 20-triol (1.6g), 20(R)-20-methoxy-dammarane-3β,12β,25-triol (0.5g) and 20(R)-22,25-dimethoxy - Dammarane-3β, 12β-diol (0.3 g).

Embodiment 2

[0019] Add 250ml of methanol to panaxadiol (5g) in a sealable container, ultrasonically dissolve, add 250ml (1%-37%) HCL, and react with microwave at 20-50°C for 0.5-2 hours. The hydrolyzate was analyzed by HPLC, and the PD conversion rate was ≥85%. After the reaction solution was neutralized, it was extracted with ethyl acetate, and the total reaction product was separated through a silica gel (200-300 mesh) column, and the mobile phase was selected as petroleum ether: acetone gradient elution (10:1, 5:1, 3:1 , 1:1), to obtain 20(R)-dammarane-3β,12β,20,25-tetraol (1.0g), 20(R)-25-methoxy-dammarane-3β,12β, 20-triol (1.1 g), 20(R)-20-methoxy-dammarane-3β,12β,25-triol (0.7g) and 20(R)-22,25-dimethoxy - Dammarane-3β, 12β-diol (0.2 g).

Embodiment 3

[0021] Add 250ml of methanol to panaxadiol (5g) in a sealable container, ultrasonically dissolve, add 250ml (1-30%) NaOH, and ultrasonically react at 20-60°C for 0.5-2 hours. The hydrolyzate was analyzed by HPLC, and the PD conversion rate was ≥80%. After the reaction solution was neutralized, it was extracted with ethyl acetate, and the total reaction product was separated through a silica gel (200-300 mesh) column, and the mobile phase was selected as petroleum ether: acetone gradient elution (10:1, 5:1, 3:1 , 1:1), to obtain 20(S)-dammarane-3β,12β,20,25-tetraol (0.8g), 20(S)-25-methoxy-dammarane-3β,12β, 20-triol (1.0g), 20(S)-20-methoxy-dammarane-3β,12β,25-triol (0.1g) and 20(S)-22,25-dimethoxy - Dammarane-3β, 12β-diol (0.1 g).

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PUM

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Abstract

The invention discloses a method for preparing a composite with antineoplastic activity by panoxadiol, which can prepare a plurality of composites with dammarane mother nuclei, wherein two groups of protopanoxadiol derivatives with obvious antineoplastic activity are contained; the invention also discloses a preparation method of the composites, wherein names of the composites are respectively as follows: 20(S), 20(R)-dammarane-3 beta, 12 beta, 20, 25-tetrol, 20(S), 20(R)-25-methoxyl group (or oxyethyl group)-dammarane-3 beta, 12 beta, 20-triol, 20(S), 20(R)-20-methoxyl group (or oxyethyl group)-dammarane-3 beta, 12 beta, 25-triol and 20(S), 20(R)-22, 25-dimethoxy (or diethoxy)-dammarane-3 beta, 12 beta-diol. The invention is simple and easy to operate and has moderate condition, easy product separation and higher yield coefficient. In the general formula of 20(S) and 20(R)-dammarane-diol derivant, R1 and R2 can be OH and CH3.

Description

Technical field: [0001] The invention relates to the field of medical technology, and relates to a method for preparing a compound with significant antitumor activity from Panaxadiol (PD), in particular to a method for producing an antitumor compound through ring opening of a side chain of Panaxdiol. Background technique: [0002] Studies have shown that 20(S) and 20(R)-dammarane-3β, 12β, 20,25-tetrol, 20(S) and 20(R)-25-methyl (or ethyl)oxy-dammarane -3β, 12β, 20-triol, 20(S) and 20(R) )-22,25-dimethyl (or ethyl)oxy-dammarane-3β, 12β-diol has significant anticancer activity and can inhibit human tumor cells, including: human breast cancer, human small cell lung cancer, Human gastric cancer, human colon cancer, human glial carcinoma, human melanoma, human cervical cancer, human liver cancer, promyelocytic leukemia, sarcoma S-180, liver cancer ascites type, mouse cervical cancer-14 and Ehrlich ascites carcinoma, etc. It can also inhibit the growth and proliferation of prost...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00A61K31/575A61P35/00A61P35/02
Inventor 赵余庆刘振洋曹家庆
Owner SHENYANG PHARMA UNIVERSITY
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