Gambogicacid derivative and its preparation method and uses in pharmacy
A technology of derivatives, gambogic acid, applied in the field of gambogic acid derivatives, preparation method and application in pharmacy
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Embodiment 1
[0064] Embodiment 1: Gambogic acid-2'-nitrooxyethyl ester (I-1)
[0065] Dissolve 250mg (0.4mmol) of gambogic acid in 15ml of acetone, add 0.18ml (2.08mmol) of dibromoethane and 0.4ml of triethylamine respectively at room temperature, the reaction solution is yellow and transparent, after the addition, reflux for 6 hours , concentrated the reaction liquid directly, put it on the column by dry method, column chromatography, eluting with petroleum ether / ethyl acetate (4:1), and prepared 80 mg of yellow oil (A-1) with a yield of about 27%. Then, 80mg (0.11mmol) of compound (A-1) was dissolved in 10ml (1:1) of anhydrous tetrahydrofuran and acetonitrile mixed solvent, and 28mg (0.17mmol) of silver nitrate was added at room temperature, and the reaction was done under reflux in the dark for 5 hours. , the reaction solution was filtered to remove the precipitate, the filtrate was concentrated, put on the column by dry method, column chromatography, petroleum ether / ethyl acetate (4:1)...
Embodiment 2
[0070] Embodiment 2: Gambogic acid-3'-nitrooxypropyl ester (I-2)
[0071] With reference to the preparation method of compound (A-1), the yellow oil (A-2 ) 750mg, yield 95%. With reference to the preparation method of compound I-1, 710mg (0.95mmol) of compound (A-2) and 242mg (1.43mmol) of silver nitrate were refluxed, and the aftertreatment was the same as above to obtain 140mg of yellow sticky substance (I-2). Rate 20%.
[0072] IR(KBr): v=3456, 2967, 2924, 2858, 1736, 1710, 1632, 1593, 1438, 1383, 1331, 1279, 1228, 1177, 1140, 1048cm -1 .
[0073] 1 HNMR (300M, CDCl 3 ): δ 12.86 (1H, s, 6-OH), 7.56 (1H, brs, H-10), 6.67 (1H, m, H-4), 6.14 (1H, m, H-27), 5.45 (1H , m, H-3), 5.06(2H, m, H-32, H-37), 4.39((2H, m, H-1'), 3.90(2H, m, H-3'), 3.48( 3H, m, H-2', H-11), 3.30 (1H, m, H-31a), 3.23 (1H, m, H-31b), 2.98 (2H, dd, J=9.7Hz, 7.9Hz, H-26), 2.52 (1H, m, H-22), 2.36 (1H, dd, J=13.0Hz, 4.6Hz, H-21a), 2.03 (2H, m, H-36), 1.75 (3H, s, H-25), 1.72 (2H, m, H-20), 1.66 (3H,...
Embodiment 3
[0076] Embodiment 3: Gambogic acid-4'-nitrooxybutyl ester (I-3)
[0077] With reference to the preparation method of compound (A-1), yellow oil (A- 3) 630 mg, yield 83%. Referring to the preparation method of compound (I-1), 630mg (1.22mmol) of compound (A-3) and 311mg (1.83mmol) of silver nitrate were refluxed, and the aftertreatment was the same as above to obtain a yellow sticky substance (I-3) 160 mg, yield 39%.
[0078] IR(KBr): v=3455, 2967, 2924, 2858, 1736, 1710, 1632, 1593, 1438, 1382, 1331, 1278, 1228, 1176, 1140, 1048cm -1 .
[0079] 1 HNMR (300M, CDCl 3 ): δ 12.86 (1H, s, 6-OH), 7.56 (1H, brs, H-10), 6.67 (1H, m, H-4), 6.11 (1H, m, H-27), 5.45 (1H , m, H-3), 5.07 (2H, m, H-32, H-37), 4.54 ((2H, m, H-1'), 3.53 (4H, m, H-2', H-3 '), 4.10(2H, m, H-4'), 3.48(1H, m, H-11), 3.30(1H, m, H-31a), 3.21(1H, m, H-31b), 2.98( 2H, dd, J=9.7Hz, 7.9Hz, H-26), 2.51(1H, m, H-22), 2.36(1H, dd, J=13.0Hz, 4.6Hz, H-21a), 2.02(2H , m, H-36), 1.75 (3H, s, H-25), 1.71 (2H, m, H-20...
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