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

Inactive Publication Date: 2009-08-12
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no report on the synthesis of nitric oxide donor-type gambogic acid derivatives using NO donors and gambogic acid

Method used

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  • Gambogicacid derivative and its preparation method and uses in pharmacy
  • Gambogicacid derivative and its preparation method and uses in pharmacy
  • Gambogicacid derivative and its preparation method and uses in pharmacy

Examples

Experimental program
Comparison scheme
Effect test

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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Abstract

The invention discloses a gambogic acid derivative, a preparation method thereof and an application in pharmacy. The gambogic acid derivative is a compound obtained by coupling a nitric oxide donor with gambogic acid through an ester bond or an amide bond. The gambogic acid derivative has an antitumor effect and can be used for preparing antitumor drugs.

Description

technical field [0001] The invention belongs to the field of pharmacy, and relates to a gambogic acid derivative with anti-tumor effect, specifically a compound that uses different types of nitric oxide (abbreviated as NO) donors to couple gambogic acid through an ester bond or an amide bond , the present invention also relates to the preparation method and application of the derivative in pharmacy. Background technique [0002] Gambogic acid, a natural compound, was isolated for the first time from the garcinia resin of plants of the genus Garcinia. Gambogic acid can selectively and effectively kill tumor cells, but has no effect on normal hematopoietic system and immune function. Studies have proved that gambogic acid and its derivatives are agonists of caspases and inducers of apoptosis , can be used as an effective inducer of apoptosis against various tumor lines. [0003] Because gambogic acid and its derivative compounds have significant cytotoxicity, in order to fin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/22C07D493/20C07D493/18A61K31/4245A61K31/352A61P35/00
Inventor 尤启冬王进欣郭青龙
Owner CHINA PHARM UNIV
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