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

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

Inactive Publication Date: 2015-12-02
CHINA PHARM UNIV
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  • 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

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  • (20s, 24s)-ocotillol type ginsenoside derivatives with antibacterial activity, preparation method and application thereof
  • (20s, 24s)-ocotillol type ginsenoside derivatives with antibacterial activity, preparation method and application thereof
  • (20s, 24s)-ocotillol type ginsenoside derivatives with antibacterial activity, 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 (58mg, 48.3%). 1 HNMR (CDCl 3 , 300MHz) δ4.09-4.15 (dd, J=11.0Hz, 7.1Hz, 1H), 3.84-3.90 (dd, J=10.4Hz, 5.1Hz, 1H), 3.48-3.57 (td, J=10.2Hz, 4.6Hz, 1H), 3.15-3.21(dd, J=11.1Hz, 5.0Hz, 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 HNMR (CDCl 3 , 500MHz) δ3.87-3.90(dd, J=10.5Hz, 5.0Hz, 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] + .

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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] Traditional Chinese medicine ginseng (PanaxginsengC.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 LarsP.Christensen.Ginsenosides: Chemistry, Biosynthesis, Analysis, and Potential Health Effects. Advances in Food and Nutrition Research, 2008, 55: 1-99). The structural types of ginsenosides are roughly divided into three types: dam...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J17/00C07J43/00A61K31/58A61P31/04
Inventor 徐进宜毕毅张恒源孟庆国周志文彼得·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