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20(SO)ortho ginseng diol derivative, medicinal composition containing them and its application

A technology of protopanaxadiol and its derivatives, which is applied in the direction of drug combination, medical preparations containing active ingredients, drug delivery, etc., to achieve the effect of reducing the activity of strong antiviral and anticancer drugs

Active Publication Date: 2005-08-10
HAINAN ASIA PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the research on 20(S)-protopanaxadiol derivatives and their medicinal uses has not been reported

Method used

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  • 20(SO)ortho ginseng diol derivative, medicinal composition containing them and its application
  • 20(SO)ortho ginseng diol derivative, medicinal composition containing them and its application
  • 20(SO)ortho ginseng diol derivative, medicinal composition containing them and its application

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0055] Preparation of 20(S)-protopanaxadiol-12β-monomethyl ether and 20(S)-protopanaxadiol-3β, 12β-dimethyl ether

[0056] 0.38g 20(S)-protopanaxadiol was dissolved in 10mL DMF, and 0.10g sodium hydride (60%) was added. After the sodium hydride is completely dissolved, add 0.20 mL of methyl iodide, heat to 70°C, and react for 5 hours. An appropriate amount of water was added to the reaction solution, and a white solid was precipitated. The precipitated solid was filtered and dried to obtain 0.70 g. Silica gel column chromatography, eluted with chloroform, to obtain two components: component 1 is 0.27g oily substance, namely 20(S)-protopanaxadiol-3β, 12β-dimethyl ether; component 2 is 0.19g white The solid is 20(S)-protopanaxadiol-12β-monomethyl ether.

[0057] R-OCH 3

[0058] 1 H-NMR (CDCl 3 )δ: 0.79, 0.88, 0.98, 1.11 (18Hs×4+CH 3 ),, 1.69, 1.82 (6Hs, s, ), 3.35 (3H, s, -O-CH 3 ),

[0059] 5.14 (1H,t,=C-H)

[0060] 13 C-NMR (CDCl 3 )δ: 130.77, 125.50 (-C=C-), 8...

preparation Embodiment 2

[0065] Preparation of 20(S)-protopanaxadiol-12β-monoethyl ether and 20(S)-protopanaxadiol-3β, 12β-diethyl ether

[0066] 0.38g 20(S)-protopanaxadiol was dissolved in 10mL DMF, and 0.10g sodium hydride (60%) was added. After the sodium hydride is completely dissolved, add 0.20 mL of bromoethane, heat to 70°C, and react for 5 hours. An appropriate amount of water was added to the reaction solution, and a white solid was precipitated. The precipitated solid was filtered and dried to obtain 0.70 g. The crude product was purified by column chromatography and eluted with chloroform to obtain two components: component 1 was 0.13g oily substance, that is, 20(S)-protopanaxadiol-3β, 12β-diethyl ether; component 2 was 0.20g white The solid is 20(S)-protopanaxadiol-12β-monoethyl ether.

[0067] R-OCH 2 CH 3

[0068] 1 H-NMR (CDCl 3 )δ: 0.67, 0.81, 0.84, 0.88, 0.90, 0.98 (18H, s×6, +CH 3 ), 1.56, 1.64 (6H, s, s, ), 1.07 (3H, t, -CH 3 ), 3.01, 3.71 (2H, q, q, -OCH 2 -), 5.12 (=...

preparation Embodiment 3

[0074] Preparation of 20(S)-protopanaxadiol-12β-n-pentyl ether

[0075] 0.38g 20(S)-protopanaxadiol was dissolved in 10mL DMF, and 0.10g sodium hydride (60%) was added. After the sodium hydride is completely dissolved, add 0.38g (0.31mL) n-pentane bromide, heat to 70°C, and react for 5 hours. Cool to room temperature, add 50mL of water, an oily substance precipitates, and stand overnight. The supernatant was decanted, washed once with water, the oil was extracted with chloroform, and the extract was dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.05 g of a light yellow oil. The crude product was purified by silica gel column chromatography and eluted with chloroform to obtain 0.38 g of the title product as a pale yellow liquid.

[0076] 1 H-NMR (CDCl 3 )δ: 0.78, 0.88, 0.95, 0.98, 1.10 (18H, s×4, +CH 3 ), 0.88 (3H, t, -CH 3 ), 1.57, 1.62 (6H, s, s, ), 5.15 (1H, t, =C-H), 8.01 (1H, s, -OH), 5.60 (1H, broad, -OH) ...

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Abstract

An antineoplastic 20(S)-protopanoxadiol derivative and its medicinal composition for treating tumor and viral diseases are disclosed.

Description

technical field [0001] The present invention relates to 20(S)-protopanaxadiol derivatives with antitumor activity, pharmaceutical compositions containing them and applications thereof. Background technique [0002] 20(S)-Protopanaxadiol (20(S)-Dama-24-ene-3β, 12β, 20β-triol) is the main active ingredient of ginseng, protopanaxadiol group saponin R b1 , R b2 , R b3 , R c , R d , Aglycones such as saponins. Japanese Open Patent Gazette (Shao 58-13199), 20(S)-protopanaxadiol, 20(R)-protopanaxadiol, 20(S)-protopanaxatriol, 20(R)-protopanaxadiol, 20(R)-protopanaxadiol Alcohols have strong anticancer activity, and 20(S)-protopanaxadiol has the strongest anticancer activity. (Tadahideota et al.J.Pharm.Sci.1991, 80(12):1141-1143) reported that 20(S)-protopanaxadiol has more tumor inhibitory activity on melanoma than ginsenoside Rh 2 stronger. Jin Yongri et al. reported (CN1416833) that 20(S)-protopanaxadiol not only has anticancer activity, but also...

Claims

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Application Information

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IPC IPC(8): A61K9/02A61K9/08A61K9/16A61K9/20A61K9/48A61K31/704A61P31/12A61P35/00C07J9/00
Inventor 楼金张龙清张兴权
Owner HAINAN ASIA PHARM CO LTD
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