A kind of paeonol acetic acid compound, its preparation method and medical application
A technology of paeonol acetic acid and compound, which is applied in the fields of medicinal chemistry and pharmacotherapeutics, and can solve the problems of easy volatility, easy metabolism, poor water solubility, limited clinical application and the like
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Embodiment 1
[0122] Preparation of paeonol acetic acid (2)
[0123]Put paeonol (1.0g, 6.0mmol), sodium hydroxide (1.5g, 37.5mmol), and appropriate amount of DMF in a 100mL round bottom flask, and stir at room temperature for 20min. Bromoacetic acid (1.5 g, 10.8 mmol) was added with stirring, and the progress of the reaction was monitored by TLC. After the reaction was complete, the reaction solution was poured into 100 mL of water, adjusted to pH 2 with hydrochloric acid, and extracted with ethyl acetate (30 mL*3). The organic layer was washed with saturated NaCl solution, anhydrous Na 2 SO 4 After drying, filter. The filtrate was concentrated under reduced pressure, and column chromatography (methanol:dichloromethane=1:20) gave 1.1 g of white solid, yield 81%.
[0124] Preparation of Paeonol Acetate-2-Bromoethyl Ester (3)
[0125] Weigh 2.0g (8.9mmol) paeonol acetic acid in a 50mL round bottom flask, add 10ml DMF to dissolve. Join K 2 CO 3 (1.8g, 13.4mmol), after stirring for five...
Embodiment 2
[0129] The method for preparing paeonol acetic acid with reference to embodiment 1.
[0130] Preparation of Paeonol Acetate-3-Bromopropyl Ester (3)
[0131] Weigh 2.0g (8.9mmol) paeonol acetic acid in a 50mL round bottom flask, add 10ml DMF to dissolve. Join K 2 CO 3 (1.8g, 13.4mmol), after stirring for five minutes, 1,3-dibromopropane (2.8ml, 26.7mmol) was added, and the reaction progress was monitored by TLC. After 2 hours of reaction, the reaction solution was poured into 100 mL of water, extracted with dichloromethane (50 mL×3), the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated, and subjected to column chromatography (ethyl acetate:petroleum ether (v: v)=1:4) to obtain 2.5 g of white solid, with a yield of 81.4%.
[0132] Paeonol acetate-3-(1-piperidinyl)propyl ester (I 8 ) preparation
[0133] Weigh 2.0g (5.8mmol) paeonol acetate-3-bromopropyl acetate, piperidine (1.7mL, 17.4mmol) in a 50mL round bottom flask, add 1...
Embodiment 3
[0135] The method for preparing paeonol acetic acid with reference to embodiment 1.
[0136] Preparation of 4-bromobutyl paeonol acetate (3)
[0137] Weigh 2.0g (8.9mmol) paeonol acetic acid in a 50mL round bottom flask, add 10ml DMF to dissolve. Join K 2 CO 3 (1.8g, 13.4mmol), after stirring for five minutes, 1,4-dibromobutane (3.2ml, 26.7mmol) was added, and the reaction progress was monitored by TLC. After 2 hours of reaction, the reaction solution was poured into 100 mL of water, extracted with dichloromethane (50 mL×3), the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated, and subjected to column chromatography (ethyl acetate:petroleum ether (v: v)=1:4) to obtain 2.6 g of white solid, yield 81.3%.
[0138] Paeonol acetate-4-[(4-methyl)-1-piperazinyl]butyl ester (I 17 ) preparation
[0139] Weigh 2.0g (5.6mmol) of 4-bromobutyl paeonol acetate and N-methylpiperazine (1.8ml, 16.2mmol) into a 50mL round bottom flask, add 1...
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