20(S) or 20(R)-dammarane-3 beta,12 beta, 20,25-tetraalcohol derivative, its salt and use thereof

A technology of dammarane and derivatives, which is applied in the field of medicine to achieve the effect of reducing activity and strong anti-virus

Inactive Publication Date: 2008-08-27
SHENYANG PHARMA UNIVERSITY
View PDF0 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For 20(S) or 20(R)-dammarane-3β, 12β, 20,25-tetraol derivatives and their uses have not been reported yet

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 20(S) or 20(R)-dammarane-3 beta,12 beta, 20,25-tetraalcohol derivative, its salt and use thereof
  • 20(S) or 20(R)-dammarane-3 beta,12 beta, 20,25-tetraalcohol derivative, its salt and use thereof
  • 20(S) or 20(R)-dammarane-3 beta,12 beta, 20,25-tetraalcohol derivative, its salt and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Preparation of dammarane-3β, 12β, 20,25-tetraol-12β-monomethyl ether and dammarane-3β, 12β, 20,25-tetraol-3β, 12β-dimethyl ether

[0033] 0.3g of dammarane-3β,12β,20,25-tetraol was dissolved in 15ml of DMF, and 0.3g of sodium hydride (60%) was added. After all the sodium hydride was dissolved, 0.2ml of methyl iodide was added, heated to 70°C, and refluxed for 8 hours. An appropriate amount of water was added to the reaction solution, and a white solid was precipitated. The precipitated solid was filtered, dried, and subjected to silica gel column chromatography, eluting with petroleum ether: acetone (3:1), to obtain two components: component 1 was a white oily dammarane-3β, 12β, 20, 25-tetra Alcohol-3β, 12β-dimethyl ether (69.7%), Fraction 2 was dammarane-3β, 12β, 20,25-tetraol-12β-monomethyl ether (48.6%) as a white solid. Example 2: Preparation of dammarane-3β, 12β, 20,25-tetraol-12β-monoethyl ether and dammarane-3β, 12β, 20,25-tetraol-3β, 12β-diethyl eth...

Embodiment 2

[0034] 0.5 g of dammarane-3β, 12β, 20, 25-tetraol was dissolved in 15 ml of DMF, and 0.5 g of sodium hydride (60%) was added. After all the sodium hydride was dissolved, 0.4 ml of ethyl bromide was added, heated to 75°C, and refluxed for 10 hours. An appropriate amount of water was added to the reaction solution, and a white solid was precipitated. The solid was separated out by filtration, dried, and subjected to silica gel column chromatography, eluting with petroleum ether: ethyl acetate (4:1), to obtain two components: component 1 was a white oily dammarane-3β, 12β, 20, 25 - Tetrol-3β, 12β-diethyl ether (25.2%), Fraction 2 is a white solid dammarane-3β, 12β, 20,25-tetraol-12β-monoethyl ether (47.3%).

Embodiment 3

[0035] Example 3: Preparation of dammarane-3β, 12β, 20,25-tetraol-12β-n-pentyl ether

[0036] 0.4 g of dammarane-3β, 12β, 20, 25-tetraol was dissolved in 18 ml of DMF, and 0.4 g of sodium hydride (60%) was added. After all the sodium hydride was dissolved, 0.3 ml of n-bromoalkane was added, heated to 80°C, and refluxed for 5 hours. An appropriate amount of water was added to the reaction solution, and an oily substance was precipitated, which was left overnight. The supernatant was decanted, washed once with water, and the oil was extracted with chloroform, and the extract was dried with anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give dammarane-3β,12β,20,25-tetraol-3β,12β-n-pentyl ether (89.5%) as a pale yellow oil.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention provides a 20(S) / 20(R)-dammarane-3beta, 12beta, 20, 25-tetraol derivative, relative salt and anti-tumor application, belonging to medical technical field, wherein the 20(S) / 20(R)-dammarane-3beta, 12beta, 20, 25-tetraol derivative and relative salt are respresented as below, the 20(S) / 20(R)-dammarane-3beta, 12beta, 20, 25-tetraol derivative and relative salt can be combined with medical acceptable carrier into drug compound, to prepare anti-virus and anti-tumor drugs. The 20(S) / 20(R)-dammarane-3beta, 12beta, 20, 25-tetraol derivative and relative salt have stronger anti-viruse and anti-tumor activity than dammarane-3beta, 12beta, 20, 25-tetraol, which can improve the activity of other anti-virus and anti-tumor drugs and reduce the toxicity.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to 20(S) or 20(R)-dammarane-3β, 12β, 20,25-tetraol derivatives, salts thereof and uses thereof. The medicine provided by the present invention containing 20(S) or 20(R)-dammarane-3β, 12β, 20,25-tetrol derivatives and salts thereof is more than 20(S) and 20(R)-protoginseng two Alcohol has stronger anticancer activity, and can also more obviously enhance the activity of other antiviral and anticancer drugs and reduce the toxic and side effects of these drugs. Background technique [0002] 20(R)-dammarane-3β, 12β, 20,25-tetrol [20(R)-25-OH-PPD] has strong anticancer activity and can inhibit human tumor cells (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 with ascites, mouse cervical cancer-14 and AI Ascites...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00A61K31/575A61P35/00A61P31/12
Inventor 赵余庆刘娜李宁
Owner SHENYANG PHARMA UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap