Application of strigolactone analog in preparation of anti inflammatory medicine

A technology of strigolactone and anti-inflammatory drugs, which is applied in the direction of anti-inflammatory agents, drug combinations, antipyretics, etc., and can solve the problems of unreported anti-inflammatory effects of strigolactones

Active Publication Date: 2015-08-26
广东汉潮中药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] There are no reports of anti-inflammatory effects of strigolactone and its analog GR24

Method used

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  • Application of strigolactone analog in preparation of anti inflammatory medicine
  • Application of strigolactone analog in preparation of anti inflammatory medicine
  • Application of strigolactone analog in preparation of anti inflammatory medicine

Examples

Experimental program
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Effect test

preparation example Construction

[0134] The preparation method of the raw material used in the embodiment is as follows:

[0135] 3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-one (4):

[0136] Take 1-indanone (5.0g, 37.88mmol) and dimethyl carbonate (13.6g, 151.11mmol) and dissolve in 15ml of anhydrous tetrahydrofuran, slowly add dropwise to 20ml of anhydrous tetrahydrofuran, sodium hydride (2.0g, 83.33mmol) In the suspension solution, protected by nitrogen, reflux at 65° C. and stir for 1.5 hours to react. Then 10 ml of tetrahydrofuran solution of ethyl bromoacetate (9.5 g, 56.89 mmol) was added, and the reaction was continued for 2 hours. After TLC monitors that the reaction of raw materials is complete, add saturated ammonium chloride solution to quench the reaction, remove the solvent under reduced pressure, extract with ethyl acetate, dry the organic phase, filter, concentrate, and purify by silica gel column chromatography to obtain 2-ethoxycarbonylmethyl- Methyl 1-oxo-indene-2-carboxylate (1) was a w...

Embodiment 1

[0142] Example 1 Preparation of Compounds 1A-1F

[0143] Dissolve 3,3a, 4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-one (1g, 5.75mmol) and methyl formate (1.96g, 32.7mmol) in 8ml of anhydrous Add this solution to a solution of sodium metal (0.26g, 11.36mmol) in tetrahydrofuran (5ml), and stir at room temperature for 2 hours under nitrogen protection. After the complete reaction of the raw materials was monitored by TLC, 5 ml of a tetrahydrofuran solution of 5-bromo-3-methyl-5H-furan-2-one (0.86 g, 4.9 mmol) was added, and stirring was continued for 2 hours. After the reaction was completed, ethanol was added to quench the reaction, the solvent was removed under reduced pressure, extracted with ethyl acetate, the organic phase was dried, filtered, concentrated, and separated by silica gel column chromatography to obtain diastereoisomers 1A and 1D. 1A, 1D were resolved by chiral column to obtain 1B, 1C and 1E, 1F respectively.

[0144]

Embodiment 2

[0145] Example 2 Preparation of Compounds 1a-1f

[0146] Dissolve 1A or (1B-1F) in ethyl acetate (10ml), add Pd / C (10%) hydrogen and react at room temperature for 3 hours. The reaction solution was filtered, and the filtrate was concentrated and separated by silica gel column chromatography to obtain 1a or (1b~1f)

[0147]

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Abstract

The invention relates to the field of medicine chemistry, and specific discloses application of a strigolactone analog in preparation of an anti inflammatory medicine. The anti-inflammatory activity of the strigolactone analog is found for the first time, and anti-inflammatory activity of two GR24 optical isomers are especially significant.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to the application of a strigolactone analogue in the preparation of anti-inflammatory drugs. Background technique [0002] Strigolactones were originally isolated from cotton root exudates and were considered stimulators of Striga spp. seed germination. Another function of it is to serve as an essential chemical signal for the connection between the root circle of plants and arbuscular mycorrhizal fungi. In addition to the above functions, strigolactone or its metabolites are also used as a new type of plant Hormones can inhibit plant branching. Its structural formula is as follows: [0003] [0004] GR24 is a synthetic analog of strigolactone, which was confirmed by British researchers in 2008 as the seventh largest plant hormone in plants. Its functions are: (1) as an environmental stimulus model, it can induce the germination of parasitic weed seeds; (2) as an allelochem...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/365A61P29/00
Inventor 孙平华郭嘉亮韩雨水孔昊王芳程涛刘康佳陈卫民刘培均林静
Owner 广东汉潮中药科技有限公司
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