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
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[0054] Preparation Example 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. Appropriate amount of water was added to the reaction solution to precipitate a white solid. The precipitated solid was filtered and dried to obtain 0.70 g. Silica gel column chromatography, eluted with chloroform, to obtain 2 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: 130.7...
Example
[0064] Preparation Example 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. Appropriate amount of water was added to the reaction solution to precipitate a white solid. The precipitated solid was filtered and dried to obtain 0.70 g. The crude product was refined by column chromatography and eluted with chloroform to obtain 2 components: component 1 was 0.13g oily substance, namely 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...
Example
[0073] Preparation Example 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, 0.38 g (0.31 mL) of n-pentane bromide is added, heated to 70° C., and reacted for 5 hours. Cool to room temperature, add 50 mL of water, precipitate an oil, and let it stand overnight. The supernatant was decanted, washed once with water, the oily substance was extracted with chloroform, and the extract was dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 1.05 g of 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, ), ...
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