A kind of ursolic acid derivative with anti-inflammatory activity and its preparation method and application
A technology of ursolic acid and its derivatives, which is applied in anti-inflammatory agents, organic chemistry, drug combinations, etc., can solve the problems of low bioavailability, limited clinical application, and lack of target specificity, and achieve high yield and significant anti-inflammatory effects. The effect of inflammatory activity
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Embodiment 1
[0039] Synthesis of compound Ⅰ-3:
[0040] Add UA (2.0g, 4.38mmol) into a 50mL eggplant-shaped bottle, dissolve it in 15mL of pyridine, control the temperature at 0°C to 10°C, slowly add acetic anhydride (1.0mL, 10.58mmol) dropwise, and stir the reaction at room temperature after the dropwise addition 14h, TLC (cyclohexane / acetone=3:1) detection showed that the reaction was complete. The reaction solution was poured into 60 mL of ice water, solids were precipitated, filtered with suction, and the filter cake was dissolved in 100 mL of ethyl acetate, washed with 1 mol / L hydrochloric acid, distilled water, and saturated aqueous sodium chloride solution, and dried overnight over anhydrous sodium sulfate. Concentrate under reduced pressure and dry in vacuo to obtain 2.02 g of 3-acetoxy-UA (2), with a yield of 92.5%.
[0041] Add compound 2 (1.16g, 2.33mmol) to a 50mL eggplant-shaped bottle, dissolve it in 15mL DMF, add 2-chloroethanol (0.58g, 7.20mmol), potassium carbonate (0.49g...
Embodiment 2
[0046] Synthesis of compound Ⅰ-6:
[0047] Add compound 5 (0.5g, 0.81mmol) into a 25mL eggplant-shaped bottle, dissolve it in 8mL DMF, add imidazole (0.1g, 1.47mmol), anhydrous potassium carbonate (0.15g, 1.09mmol) and react in an oil bath at 80°C for 30min TLC (cyclohexane / acetone=3:1) detection showed that the reaction was complete. The reaction solution was poured into 40 mL of ice water, white solids precipitated out, suction filtered, and the filter cake was dissolved in 100 mL of ethyl acetate, washed with distilled water and saturated aqueous sodium chloride solution (twice) successively, dried over anhydrous sodium sulfate, and placed on a silica gel column. Chromatographic purification (petroleum ether / ethyl acetate=5:1) gave 0.40 g of compound I-1 as a white powder with a yield of 83.8%.
[0048] Add Ⅰ-1 (0.3g, 0.51mmol) into a 50mL eggplant-shaped bottle, dissolve it in 24mL methanol / water (v / v=5:1), add sodium hydroxide (0.1g, 2.50mmol), and stir the reaction at 3...
Embodiment 3
[0052] Synthesis of compound Ⅰ-10:
[0053] Add compound 5 (0.5g, 0.81mmol) into a 25mL eggplant-shaped bottle, dissolve it in 8mL DMF, add pyrrole (80mg, 1.19mmol), anhydrous potassium carbonate (0.15g, 1.09mmol) and react in an oil bath at 80°C for 30min, then TLC (cyclohexane / acetone=3:1) detection showed that the reaction was complete. The reaction solution was poured into 40 mL of ice water, white solids precipitated out, suction filtered, and the filter cake was dissolved in 100 mL of ethyl acetate, washed with distilled water and saturated aqueous sodium chloride solution (twice) successively, dried over anhydrous sodium sulfate, and placed on a silica gel column. Chromatographic purification (petroleum ether / ethyl acetate 5:1) gave 350 mg of compound Ⅰ-5 as a white powder with a yield of 73.4%.
[0054] Referring to the synthesis method of compound I-6, substituting I-1 with I-5, the compound I-10 was obtained as a white powder with a yield of 83.5%. mp: 89.5-91.0°C....
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