Naringenin fatty acid ester, preparation method thereof, pharmaceutical composition containing the compound as active ingredient and application thereof
A technology of fatty acid esters and naringenin, which is applied in the field of anti-platelet aggregation, can solve the problems of literatures where the 5-hydroxyl esterification of naringenin has not been found, and achieve improved druggability, solubility, and industrialization The effect of production
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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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