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Substituted andrographolide derivative, preparing method and pharmaceutical compound thereof

An unsubstituted and compound technology, which is applied in the field of substituted andrographolide derivatives, can solve problems such as no reports on the activity of andrographolide derivatives

Inactive Publication Date: 2007-08-08
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] There is no report in the existing literature about the activity of andrographolide derivatives to inhibit the expression of COX-2, TNF-α and IL-6

Method used

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  • Substituted andrographolide derivative, preparing method and pharmaceutical compound thereof
  • Substituted andrographolide derivative, preparing method and pharmaceutical compound thereof
  • Substituted andrographolide derivative, preparing method and pharmaceutical compound thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0113] 3, the preparation of 19-isopropylidene andrographolide (2):

[0114] In a 500ml round bottom flask, add 15.0g andrographolide (1) (42.9mmol), 20ml2,2-dimethoxypropane, catalytic amount of pyridinium p-toluenesulfonate (PPTs), 300ml benzene, 40ml DMSO, heat to reflux 30min, the reaction is complete. Cool the reaction solution to room temperature, add triethylamine (about 10ml) to adjust the pH to 8, add 200ml benzene to dilute the reaction solution, wash with saturated brine (300ml×3), dry over anhydrous sodium sulfate, filter and concentrate, solids are precipitated, filter 15.0 g of white solid was obtained, yield 90%, mp: 194-196° C. (documentation mp: 194.5° C.).

Embodiment 2

[0116] 3, the preparation of 19-isopropylidene-12-hydroxyl-andrographolide (3):

[0117] Add 4.0g2 (10.3mmol), 5.0gPDC (13.3mmol), and 60ml of dichloromethane into a 100ml round bottom flask, heat to reflux, and monitor the reaction by TLC. After the reaction was completed, the heating was stopped, cooled to room temperature, and separated by column chromatography (petroleum ether: ethyl acetate = 3:2) to obtain 2.8 g of a white solid, with a yield of 70%.

Embodiment 3

[0119] 12-propionyloxy-14-deoxyandrographolide (IA 1 ) preparation:

[0120] Add 1.0g3 (2.6mmol), 2ml propionic anhydride (21.2mol), catalytic amount of DMAP, 25ml dichloromethane into a 50ml round bottom flask, react at 25°C for 12h, evaporate the solvent under reduced pressure, and dissolve the residue with 150ml ethyl acetate , washed with saturated brine, dried over anhydrous sodium sulfate, and evaporated to obtain light-colored oil 4. Add 7ml of acetic acid, 3ml of water, and react at 25°C for 1h. The reaction solution was dissolved in 100ml of ethyl acetate, saturated saline, and saturated carbonic acid Sodium hydrogen solution was washed to pH about 7, dried over anhydrous sodium sulfate, and the solvent was evaporated to obtain a light-colored oil, which was separated by column chromatography (petroleum ether: ethyl acetate = 3:2) to obtain 0.63 g of a white solid. Rate 60%, mp: 141-142°C.

[0121] IR (KBr) v: 3342, 3133, 2939, 2864, 1754, 1730, 1646, 1446, 1341, 11...

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Abstract

The invention discloses a compound and medical acceptable salt with general formula (I) and making method and their drug agent, which possesses better COX-2 expressive inhibiting and TNF-alpha inhibiting and IL-6 inhibiting action.

Description

technical field [0001] The present invention relates to substituted andrographolide derivatives, their synthesis methods, and pharmaceutical compositions containing them. Background technique [0002] Andrographolide is one of the main active ingredients of Andrographis paniculata (Burm.f.) Nees, a plant of the Acanthaceae family. Antipyretic, anti-inflammatory (Deng Wenlong, et al. Acta Pharmaceutica Sinica, 1980, 15(10): 590), analgesic, antibacterial (Xu Luoshan et al., Chinese Materia Medica (Volume 2). Beijing: China Medical Science and Technology Press, 1996: 1580), hypoglycemic, anti-atherosclerosis and other extensive physiological activities, it is mainly used clinically to treat diseases such as upper respiratory tract infection. With the continuous deepening of the research on the pharmacological effects of andrographolide, it has shown attractive application prospects in immune regulation, anti-virus, anti-tumor and other aspects. (Dai Guifu, Wang Junfeng, He S...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/58C07D407/12C07D207/277A61K31/365A61K31/4015A61P43/00
Inventor 黄文龙张惠斌李晶周慧萍
Owner CHINA PHARM UNIV
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