Ginsenoside CK derivative and application thereof in preparation of antitumor drugs

A technology of ginsenosides and derivatives, applied in the direction of antineoplastic drugs, drug combinations, glycoside steroids, etc., can solve the problems of limited CK sources, poor water solubility of ginsenoside CK derivatives, difficult separation and purification, etc., and achieve good inhibitory effect

Active Publication Date: 2021-10-22
SHAANXI GIANT BIOTECHNOLOGY CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, CK sources are limited and difficult to separate and purify
However, the series of ginsenoside CK derivatives obtained by chemical synthesis technology have poor water solubility.

Method used

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  • Ginsenoside CK derivative and application thereof in preparation of antitumor drugs
  • Ginsenoside CK derivative and application thereof in preparation of antitumor drugs
  • Ginsenoside CK derivative and application thereof in preparation of antitumor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0095] Embodiment 1 synthetic compound CK-1

[0096] Weigh 500mg of ginsenoside CK with an electronic balance, dissolve it in 25mL of anhydrous dichloromethane, add 5mL of triethylamine and 1mL of tert-butyldiphenylchlorosilane in turn at 0°C, keep this temperature for 10min, and naturally rise to Reaction at room temperature for 8h. After thin-layer chromatography TLC (D / M=10:1) monitoring is complete, add saturated ammonium chloride to stop the reaction, extract 3 times with 25mL dichloromethane, the obtained organic phase is washed with saturated brine, dried over anhydrous sodium sulfate, filtered, Concentrated under reduced pressure, the obtained concentrate was purified by silica gel column chromatography (D / M=10:1), and the obtained product CK-1 (600 mg, yield 88.4%) was a white solid. MS(ESI): calcd for C 52 h 81 o 8 Si[M+H] + 861.5695, found 861.5678.

Embodiment 2

[0097] Embodiment 2 synthetic compound CK-2 and CK-2-2

[0098] Weigh 136mg of ginsenoside CK-1 with an electronic balance, then weigh 10mg of 4-dimethylaminopyridine (DMAP), dissolve it in 3mL of triethylamine and 5mL of dichloromethane, and fully stir , into the nitrogen protection. Then place the three-necked round-bottomed flask under ice bath conditions, and add 0.30 mL of acetic anhydride AC to the reaction solution. 2 O, after 10 min, it was raised to room temperature to continue the reaction, and the reaction progress was monitored by TLC (P / E=1:1). After reacting for 6 hours, add saturated ammonium chloride to stop the reaction, extract 3 times with 5 mL of dichloromethane, wash the obtained organic phase with saturated brine, dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure, and the obtained concentrate is subjected to silica gel column chromatography After purification (P / E=3:1), the obtained products CK-2 (131 mg, yield 77.5%) and...

Embodiment 3

[0101] Embodiment 3 synthetic compound CK-2A

[0102] Take by weighing the ginsenoside CK of 100mg with electronic balance, then weigh the 4-dimethylaminopyridine (DMAP) of 12mg, it is dissolved in the dichloromethane of the triethylamine of 2.5mL and 5mL, and carry out sufficient stirring, Introduce nitrogen protection. Then place the three-necked round-bottomed flask under ice bath conditions, and add 0.30 mL of acetic anhydride AC to the reaction solution. 2 O, rose to room temperature after 10 min to continue the reaction. Thin-layer chromatography TLC (P / E=1:1) monitors that the reaction is complete, add saturated ammonium chloride to stop the reaction, extract 3 times with 5mL dichloromethane, wash the obtained organic phase with saturated brine, dry over anhydrous sodium sulfate, and filter , concentrated, and the obtained concentrate was purified by silica gel column chromatography (P / E=2:1), and the obtained product CK-2A (130 mg, yield 92.8%) was a white solid. Th...

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PUM

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Abstract

The invention relates to a ginsenoside CK derivative, a pharmaceutical composition containing the ginsenoside CK derivative and application of the ginsenoside CK derivative and the pharmaceutical composition.

Description

technical field [0001] The invention belongs to the technical field of chemical medicines, and in particular relates to ginsenoside CK derivatives and their application in the preparation of antitumor drugs. Background technique [0002] Ginseng has anti-aging, anti-inflammatory, anti-allergic, hypoglycemic, repairing nerve damage and liver protection effects. Studies in recent years have shown that ginsenosides have anti-tumor effects, and most of them focus on Rg3, Rh1, Rh2, etc. as the main research objects. They have shown significant effects in promoting tumor cell apoptosis and tumor cell differentiation. Ginsenosides with different structures have different antitumor activities, and the antitumor activity of diol-type ginsenosides is significantly stronger than that of triol-type ginsenosides. With the in-depth study of saponin pharmacokinetics, it is found that the real anti-tumor effect is the secondary metabolite Compound K of saponins in animals, also known as gi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J17/00C07J43/00C07J41/00A61K31/7032A61K31/7056A61P35/00
CPCC07J17/005C07J43/003C07J41/0055A61P35/00
Inventor 范代娣刘庆超段志广殷诗玉同杨柳严建亚
Owner SHAANXI GIANT BIOTECHNOLOGY CO LTD
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