Diosgenin amino acid derivative and application thereof to antitumor drug

A technology of diosgenin and derivatives, applied in the field of medicine

Inactive Publication Date: 2014-12-31
JILIN AGRICULTURAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the method of forming a salt with an acid or a base has great limitations, and this method can only be used for components with acidity or alkalinity; It is slow, but the bioavailability is very high....

Method used

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  • Diosgenin amino acid derivative and application thereof to antitumor drug
  • Diosgenin amino acid derivative and application thereof to antitumor drug
  • Diosgenin amino acid derivative and application thereof to antitumor drug

Examples

Experimental program
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Effect test

example 1

[0034] Preparation of L-phenylalanine diosgenin ester:

[0035]Weigh 0.1000 g (0.24 mmol) of diosgenin, 0.1280 g (0.48 mmol) of N-BOC-L phenylalanine, 0.1000 g (0.48 mmol) of DCC, 0.058 g (0.48 mmol) of DMAP, and an appropriate amount of molecular sieves into 50 mL of reaction Add 25 mL of dichloromethane to the bottle, place the reaction mixture on a magnetic stirrer at room temperature to accelerate the reaction, and use TLC (petroleum ether-ethyl acetate = 4:1 v:v) to detect the reaction progress, and each Check every 15 minutes. During the reaction process, new substances will be produced, and the reaction is stopped when the reaction is complete, and the reaction time is about 2 h. Filter the liquid in the reaction bottle, evaporate the solvent under reduced pressure until 2-3 mL of liquid remains in the round bottom flask to stop the reaction, pour the remaining liquid into an evaporating dish, and evaporate in a water bath (temperature 45 ℃) in a fume hood , evaporate...

example 2

[0037] Preparation of L-alanine diosgenin ester:

[0038] Weigh 0.1000 g (0.24 mmol) of diosgenin, 0.0908 g (0.48 mmol) of N-BOC-L-alanine, 0.1000 g (0.48 mmol) of DCC, 0.058 g (0.48 mmol) of DMAP, and an appropriate amount of molecular sieves into 50 mL of reaction 25 mL of dichloromethane was added to the bottle, and the reaction mixture was reacted under magnetic stirring at room temperature, and the reaction progress was detected by TLC (petroleum ether-ethyl acetate=4:1 v:v) every 15 min. During the reaction process, new substances will be produced, and the reaction is stopped when the reaction is complete, and the reaction time is about 24 h. Filter the liquid in the reaction bottle, evaporate the solvent under reduced pressure until 2-3 mL of liquid remains in the round bottom flask to stop the reaction, pour the remaining liquid into an evaporating dish, and evaporate in a water bath (temperature 45 ℃) in a fume hood , evaporated until it was mucus, and purified by si...

example 3

[0040] Preparation of L-proline diosgenin ester:

[0041] Weigh 0.1000 g (0.24 mmol) of diosgenin, 0.1033 g (0.48 mmol) of N-BOC-L-proline, 0.1000 g (0.48 mmol) of DCC, 0.058 g (0.48 mmol) of DMAP, and appropriate amount of molecular sieves into 50 mL of reaction Add 25 mL of tetrahydrofuran to the bottle, and the reaction mixture reacts under magnetic stirring at room temperature. TLC (petroleum ether-ethyl acetate=4:1 v:v) is used to detect the reaction progress, and the detection is performed every 15 min. During the reaction process, new substances will be produced, and the reaction is stopped when the reaction is complete, and the reaction time is about 2 h. Filter the liquid in the reaction bottle, evaporate the solvent under reduced pressure until 2-3 mL of liquid remains in the round bottom flask to stop the reaction, pour the remaining liquid into an evaporating dish, and evaporate in a water bath (temperature 45 ℃) in a fume hood , evaporated until it was mucus, ...

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Abstract

The invention discloses a series of amino acid derivatives prepared by using diosgenin as a lead compound through corresponding chemical reaction. Solubility test finds that the solubility of derivatives is increased compared with the raw material medicine of diosgenin; and the pharmacological experiments prove that the diosgenin amino acid derivatives have in vitro antitumor activity, have different degrees of growth inhibition on human colon cancer cell Caco-2, human gastric carcinoma cell MGC-709, human lung adenocarcinoma cell SPC-A-1 and human neuroblastoma cell SH-SY5Y, and have anti tumor activity similar to that of a nuclear parent compound diosgenin.

Description

technical field [0001] The present invention relates to a method for preparing amino acid derivatives of diosgenin. Specifically, a series of derivatives are prepared by using diosgenin, a raw material extracted and separated from traditional Chinese medicine, as a lead compound, and the structure is modified by taking antitumor activity as an index. , belonging to the field of medicine. Background technique [0002] Diosgenin (diosgenin) is a class of steroidal saponins, widely found in plants such as Dioscoreaceae, Liliaceae, Caryophyllaceae, Rosaceae, etc. It is an active ingredient of various plants and an important raw material for the synthesis of steroid hormone drugs. It has significant pharmacological activities such as anti-tumor, lowering blood fat, lowering blood sugar, anti-thrombotic, anti-inflammatory, etc., especially its anti-tumor effect has attracted great attention of scholars at home and abroad. [0003] There have been many reports on the anti-tumor me...

Claims

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Application Information

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IPC IPC(8): C07J71/00A61P35/00
Inventor 何忠梅祝洪艳赵岩郜玉钢陈红岩李阔南敏伦徐冰芳
Owner JILIN AGRICULTURAL UNIV
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