Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

(20S,24S)-ocotillol ginsenoside derivatives with antibacterial activity, and preparation method and application thereof

A technology of compounds and medicinal salts, applied in the field of new -ocotillol ginsenoside derivatives, which can solve the problems of low water solubility and limited application of ginsenosides

Inactive Publication Date: 2013-01-16
CHINA PHARM UNIV
View PDF5 Cites 19 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the low water solubility of ginsenosides, its clinical application is limited

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
  • (20S,24S)-ocotillol ginsenoside derivatives with antibacterial activity, and preparation method and application thereof
  • (20S,24S)-ocotillol ginsenoside derivatives with antibacterial activity, and preparation method and application thereof
  • (20S,24S)-ocotillol ginsenoside derivatives with antibacterial activity, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] (20S, 24S)-epoxydammarane-3β, 12β, 25-triol

[0074] Dissolve 20(S)-protopanaxadiol (500mg, 1.08mmol) in anhydrous pyridine (3ml), add DMAP (20mg, 0.16mmol), stir well and slowly add acetic anhydride (0.42ml, 4.43mmol) dropwise , stirred at room temperature for 12h. Dilute with ethyl acetate (20ml), wash with 10% hydrochloric acid until acidic, wash with water, wash with saturated brine, dry over anhydrous sodium sulfate, filter, concentrate, and column chromatography (petroleum ether: ethyl acetate = 10:1) to give white Solid A-1 (508 mg, 85%).

[0075] The A-1 (208mg, 0.38mmol) obtained above was dissolved in anhydrous dichloromethane (6ml), and m-chloroperoxybenzoic acid (185mg, 75%, 0.16mmol) was slowly added dropwise under pre-cooling in an ice-salt bath. Dichloromethane (5ml) solution, half an hour after the dropwise addition was completed, it was raised to room temperature and stirred for 2h. Add isopropanol (0.1ml), continue to stir for one hour, add saturate...

Embodiment 2

[0078] (20S, 24S)-epoxydammarane-3β, 6α, 12β, 25-tetrol

[0079] Using 20(S)-protopanaxatriol as raw material, the reference (20S, 24S)-epoxydammarane-3β, 12β, 25-triol synthesis method was implemented to obtain a white solid (58 mg, 48.3%). 1 H NMR (CDCl 3 , 300MHz) δ4.09-4.15 (dd, J = 11.0Hz, 7.1 Hz, 1H), 3.84-3.90 (dd, J = 10.4Hz, 5.1 Hz, 1H), 3.48-3.57 (td, J = 10.2Hz, 4.6Hz, 1H), 3.15-3.21(dd, J=11.1Hz, 5.0 Hz, 1H), 2.21-2.29(td, J=10.6Hz, 4.1Hz, 1H), 1.32(s, 3H), 1.27(s , 3H), 1.23(s, 3H), 1.10(s, 3H), 1.09(s, 3H), 0.98(s, 3H), 0.94(s, 6H). MS (ESI) m / z: 493.3 [M+H ] +.

Embodiment 3

[0081] (20S, 24S)-epoxydammarane-12β, 25-diol-3-one

[0082] Compound 2 (40mg, 0.08mmol) was dissolved in anhydrous dichloromethane (3ml), PCC (pyridinium chlorochromate, 36mg, 0.17mmol) was added, and stirred at room temperature for 3 hours. The solvent was removed under reduced pressure, dissolved in ethyl acetate, extracted, the organic layer was washed with water, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated, and column chromatography (petroleum ether:ethyl acetate=10:1) to obtain a white solid ( 23 mg, 58%). 1 H NMR (CDCl 3 , 500 MHz) δ3.87-3.90 (dd, J = 10.5Hz, 5.0 Hz, 1H), 3.52-3.57 (td, J = 10.0Hz, 4.5Hz, 1H), 2.49-2.54 (m, 1H), 2.42 -2.48(ddd, J=11.0Hz, 8.0Hz, 3.5Hz, 1H), 2.24-2.29(td, J=10.5Hz, 4.5Hz, 1H), 1.28(s, 3H), 1.23(s, 3H), 1.11(s, 3H), 1.08(s, 3H), 1.053(s, 3H), 1.046(s, 3H), 0.96(s, 3H), 0.93(s, 3H). MS (ESI) m / z: 475.3 [M+H] + .

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 relates to the fields of organic synthesis and pharmacochemistry, particularly (20S,24S)-ocotillol ginsenoside derivatives, of which the structure is disclosed as general formula (I). The invention also discloses a preparation method of the (20S,24S)-ocotillol ginsenoside derivatives, a pharmaceutical composition containing the (20S,24S)-ocotillol ginsenoside derivatives, and application of the (20S,24S)-ocotillol ginsenoside derivatives in bacterial infection disease inhibition. General formula (I).

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a new class of (20S, 24S)-ocotillol type ginsenoside derivatives, their preparation method, their pharmaceutical composition and their antibacterial infection and disease application. Background technique [0002] The traditional Chinese medicine ginseng (Panax ginseng C.A. Mey) has been used for thousands of years in my country. Ginsenosides are considered to be the main active components of ginseng. Modern medical research has proved that ginsenosides have anti-tumor, immune regulation, anti-inflammatory and anti-allergic, anti-diabetic, anti-atherosclerosis and anti-hypertensive, central and metabolic regulation activities (see Lars P. Christensen. Ginsenosides: Chemistry , Biosynthesis, Analysis, and Potential Health Effects. Advances is Food and Nutrition Research, 2008, 55: 1-99). The structural types of ginsenosides are roughly divided into three...

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
IPC IPC(8): C07J17/00C07J43/00A61K31/58A61P31/04
Inventor 徐进宜毕毅张恒源周志文彼得・约翰・刘易斯马聪陈夏张冬田华解晓妮黄文文卓小斌
Owner CHINA PHARM UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com