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Naringenin fatty acid ester and preparation method thereof as well as pharmaceutical composition with naringenin fatty acid ester as active component and application of pharmaceutical composition

A technology of fatty acid ester and naringenin, which is applied in the application field of anti-platelet aggregation, can solve the problems such as the literature that has not found the 5-hydroxyl esterification of naringenin, and achieves improved druggability, high yield, and improved drug resistance. effective effect

Active Publication Date: 2015-03-04
WEIFANG MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] However, so far, no literature on the esterification of the 5-hydroxyl group of naringenin has been found, and there is no report on the application of the esterified product naringenin-5-O-fatty acid ester to platelet aggregation.

Method used

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  • Naringenin fatty acid ester and preparation method thereof as well as pharmaceutical composition with naringenin fatty acid ester as active component and application of pharmaceutical composition
  • Naringenin fatty acid ester and preparation method thereof as well as pharmaceutical composition with naringenin fatty acid ester as active component and application of pharmaceutical composition
  • Naringenin fatty acid ester and preparation method thereof as well as pharmaceutical composition with naringenin fatty acid ester as active component and application of pharmaceutical composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Synthesis of Naringenin-5-O-Acetate

[0069] (1) Synthesis of 7,4'-O,O-dibenzylnaringenin

[0070] Naringenin (0.01mol, 2.72g) was dissolved in anhydrous N,N-dimethylformamide at a concentration of 0.3mol / L under nitrogen protection, and K was added at a concentration of 0.6mol / L 2 CO 3 (0.02mol, 2.76g), stirred at room temperature 25°C for 1 hour, then slowly added benzyl bromide (0.02mol, 2.40mL) dropwise at a concentration of 0.6mol / L under stirring, after the addition was completed, the temperature was raised to 40°C and the reaction was stirred . The progress of the reaction was monitored with GF254 silica gel thin-layer chromatography plate, developing solvent: ethyl acetate / acetone / glacial acetic acid (6:6:1.5). After 4 hours of reaction, the naringenin spots disappeared, and the benzylation reaction was complete. The reaction solution was poured into ice water, adjusted to pH=6 with 10wt% acetic acid aqueous solution, filtered, and the filter cake was washed...

Embodiment 2

[0081] Synthesis of Naringenin-5-O-propionate

[0082] (1) Synthesis of 7,4'-O,O-dibenzylnaringenin

[0083] Naringenin (0.01mol, 2.72g) was dissolved in anhydrous N,N-dimethylformamide at a concentration of 0.05mol / L under nitrogen protection, and K was added at a concentration of 0.1mol / L 2 CO 3 (0.02mol, 2.76g), stirred at room temperature 25°C for 1 hour, then slowly added benzyl bromide (0.02mol, 2.40mL) dropwise at a concentration of 0.1mol / L under stirring, after the dropwise addition was completed, the temperature was raised to 100°C and the reaction was stirred . The progress of the reaction was monitored with GF254 silica gel thin-layer chromatography plate, developing solvent: ethyl acetate / acetone / glacial acetic acid (6:6:1.5). After 6 hours of reaction, the naringenin spots disappeared, and the benzylation reaction was complete. The reaction solution was poured into ice water, adjusted to pH=6 with 10wt% acetic acid aqueous solution, filtered, and the filter c...

Embodiment 3

[0094] Synthesis of naringenin-5-O-n-butyrate

[0095] (1) Synthesis of 7,4'-O-dibenzylnaringenin

[0096] Naringenin (0.01mol, 2.72g) was dissolved in anhydrous N,N-dimethylformamide at a concentration of 0.5mol / L under nitrogen protection, and K was added at a concentration of 1.0mol / L 2 CO 3 (0.02mol, 2.76g), stirred at room temperature 25°C for 1 hour, then slowly added benzyl bromide (0.02mol, 2.40mL) dropwise at a concentration of 1.0mol / L under stirring, and stirred at 10°C after the addition was complete. The progress of the reaction was monitored with GF254 silica gel thin-layer chromatography plate, developing solvent: ethyl acetate / acetone / glacial acetic acid (6:6:1.5). After 5 hours of reaction, the naringenin spots disappeared, and the benzylation reaction was complete. The reaction solution was poured into ice water, adjusted to pH=6 with 10wt% acetic acid aqueous solution, filtered, and the filter cake was washed with water until neutral to obtain 7,4'-O,O-di...

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Abstract

The invention discloses a naringenin fatty acid ester. The naringenin fatty acid ester is naringenin fatty acid ester-5-O-fatty acid ester obtained by esterification of the fifth potential hydroxyl of naringenin. The invention also discloses a method for preparing the naringenin fatty acid ester-5-O-fatty acid ester, a pharmaceutical composition prepared with the naringenin fatty acid ester-5-O-fatty acid ester as the active component and an application of the pharmaceutical composition in inhibition of ADP, AA and collagen-induced platelet aggregation as well as cardiovascular diseases caused by platelet aggregation.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to naringenin-5-O-fatty acid ester, a preparation method thereof, a pharmaceutical composition containing the compound as an active ingredient, and their application in anti-platelet aggregation. Background technique [0002] Naringenin is a kind of natural flavonoids, which widely exists in natural plants such as Citrus aurantium, Juhong, peach leaf, and Smilax, and has low toxic and side effects, and the extraction and separation process is mature and simple. Naringenin is the aglycone of naringin, which belongs to dihydroflavonoids, has antibacterial, anti-inflammatory, free radical scavenging, anti-oxidation, cough and expectorant, blood lipid lowering, anti-cancer and anti-tumor, antispasmodic and choleretic, preventive And treatment of liver disease, inhibition of platelet aggregation, anti-atherosclerosis, etc., can be widely used in medicine, food and other field...

Claims

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Application Information

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IPC IPC(8): C07D311/32A61K31/352A61P7/02A61P9/00
CPCC07D311/32
Inventor 段煜
Owner WEIFANG MEDICAL UNIVERSITY
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