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Hedera saponin derivatives and their application in the preparation of drugs for preventing and treating senile dementia

A technology of helexin and senile dementia, which can be used in drug combinations, steroids, organic chemistry, etc., and can solve problems such as reports that no application has been found.

Inactive Publication Date: 2019-06-07
JILIN ACAD OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Before the completion of the present invention, there was no report in the literature that the acylaminoethanol derivatives of helexin had the ability to prevent and treat senile dementia, and there was no report on the application of the derivatives in the preparation of drugs for preventing and treating senile dementia.

Method used

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  • Hedera saponin derivatives and their application in the preparation of drugs for preventing and treating senile dementia
  • Hedera saponin derivatives and their application in the preparation of drugs for preventing and treating senile dementia
  • Hedera saponin derivatives and their application in the preparation of drugs for preventing and treating senile dementia

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0052] Preparation of (3β,4a)-3,23-dihydroxyolean-12-en-28-acid (compound Ⅰ, hedera saponin)

[0053] Take 1 kg of Dipsacus medicinal material, and reflux extract with 8 times the amount of 75% ethanol for 3 times. For 3 hours each time, combine three extracts, add 30g of calcium oxide, stir, stand overnight, filter, adjust the pH of the filtrate to 6-7 with dilute hydrochloric acid, add 200g of activated carbon, stir, filter, and recover ethanol from the filtrate until it is free of alcohol Add water to 2000ml, pass through the treated macroporous resin column, first wash 3 times the column volume with 20% ethanol with a pH value of 12, then wash with water until neutral, finally elute with 70% ethanol, collect 70% The eluate was concentrated to dryness under reduced pressure; hydrolyzed with 12 times the amount of 2N hydrochloric acid and 40% ethanol for 3 hours. Filtrate, discard the hydrolyzate, wash the filter cake with deionized water until neutral; then heat to boiling...

example 2

[0055] Preparation of (3β,4a)-3,23-diacetyl-olean-12-ene-28-acid (compound Ⅱ):

[0056] Take 10mmol of compound N1 (RA, 4.72g), add 200mL of pyridine, 100mL of acetic anhydride, react at 80°C, and detect the end point of the reaction by TLC. After the reaction is completed, recover the solvent under reduced pressure, add water to 250mL, and adjust the pH to 5 with dilute hydrochloric acid. , filtered, the filter cake was washed with water until colorless, dissolved in 250 mL of ethyl acetate, washed twice with water, 100 mL each time, washed three times with 10% sodium carbonate, 100 mL each time, and then washed with 100 mL of 1mol / L hydrochloric acid Wash once, and finally wash twice with water, 100 mL each time, recover ethyl acetate to dryness, add 300 mL of ethanol for recrystallization, and dry to obtain compound II (3.88 g). Yield 69.9%. White powder; mp 298~299℃; IR(KBr)ν max :3 597,3 443,2 955,2 873,1 727,1 704,1 472,1 370,1 036,924cm -1 ; HR-ESI-MS m / z: 557.380 4 ...

example 3

[0058] Preparation of 2-[(3β,4a)-3,23-diacetyl-olean-12-en-28-yl]-aminoethanol (compound Ⅲ)

[0059] Take 1.3mmol of compound N2 (0.723g), dissolve it in 15mL of dichloromethane, add 1.2mL of oxalyl chloride, react in ice bath for 1h, then react at room temperature, and detect the end point of the reaction by TLC. After the reaction is completed, concentrate under reduced pressure at 30°C to dry. Add dichloromethane to recover under reduced pressure, repeat 3 times, 50mL each time, dissolve with 8mL of dichloromethane, adjust the pH to 9-10 with triethylamine, add 0.8mL of ethanolamine, react at room temperature for 1.5h, add 50mL of water, dissolve with dilute hydrochloric acid Adjust the pH to 3-4, recover the solvent, filter, recrystallize the filter residue with 300mL of ethanol, dry, separate by silica gel column chromatography, and wash with petroleum ether (60-90°C)-ethyl acetate (1:3) as developing solvent Removed, combined the same components, recovered the solvent, ...

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PUM

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Abstract

The invention discloses a series of derivatives prepared with hederagenin as a lead compound through corresponding chemical reactions, wherein hederagenin is extracted, separated and purified from dried root of a dipsacaceous plant Dipsacus asperoides C. Y. Cheng et T. M. Ai. The derivatives have obviously improved solubility and an increased drug dissolution degree compared with the parent nucleus of hederagenin. Results of animal experiments show that the hederagenin derivative 2-[(3beta,4alpha)-3,23-diacetyl-12-oleanene-28-acyl]aminoethanol has good prevention and treatment effect on senile dementia.

Description

technical field [0001] The present invention relates to a kind of hedera saponin obtained from natural medicine, and the preparation method of synthesizing derivatives, precisely a kind of chemical composition extracted from traditional Chinese medicine is used as lead compound to prepare 2-[(3β,4a) -3,23-Diacetyl-olean-12-en-28-yl]-aminoethanol. Pharmacodynamic experiments prove that the derivative has the effect of preventing and treating senile dementia, and belongs to the technical field of medicine. Background technique [0002] Hederagenin is a pentacyclic triterpenoid obtained from the dried root of Dipsacus asperoides C.Y.Cheng et T.M.Ai through extraction, purification, separation and alkali degradation. The research of Lou Lili et al. has shown that hedera saponin has the pharmacological activity of preventing and treating senile dementia (Lou Lili et al., Research progress of anti-senile dementia natural products, Journal of Shenyang Pharmaceutical University, 20...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00A61P25/28
CPCC07J63/008
Inventor 赫玉芳南敏伦赵昱玮吕娜马吉胜王莲萍
Owner JILIN ACAD OF TRADITIONAL CHINESE MEDICINE