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Novel synthesis method of murrayone and novel application of murrayone

A synthesis method and a technique for jurisone, applied in the field of medicine, can solve the problems of complex process, difficult operation, harsh conditions and the like, and achieve the effects of simple operation, easy availability of raw materials and mild reaction conditions

Inactive Publication Date: 2012-07-25
GANNAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the isolation of Jiulixiangone from natural plants is not only limited in raw materials, but also complicated in process and high in cost.
The semi-synthesis of Jiulixiangone is prepared by the Pharmacopoeia method, the conditions are relatively harsh, the operation is relatively difficult, and the yield is relatively low.

Method used

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  • Novel synthesis method of murrayone and novel application of murrayone
  • Novel synthesis method of murrayone and novel application of murrayone
  • Novel synthesis method of murrayone and novel application of murrayone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1 9

[0021] Embodiment 1 Jiu Lixiang ketone synthetic preparation-I

[0022] Step A: Dissolve 19.6 g (0.1 mol) of 2,6-dimethoxyphenylacetic acid in 200 ml of anhydrous CH 2 Cl 2 10.9ml (0.115mol) BBr was added dropwise under stirring at -30°C 3 , after the dropwise addition, the reaction temperature was raised to room temperature, stirred overnight, and quenched by adding ice water after 10 hours of reaction, and the water phase was decomposed with CH 2 Cl 2 Extract three times, combine the organic phases, distill off the CH 2 Cl 2 , 11.4 g of 2-hydroxy-6-methoxyphenylacetic acid could be obtained by column chromatography (yield: 62.8%). used directly in the next reaction.

[0023] Step B: Mix 9.1g (0.05mol) of 2-hydroxy-6-methoxyphenylacetic acid with 17.5ml (0.175mol) of ethyl propiolate, add 6.8g of anhydrous aluminum trichloride under stirring, and heat To 100°C, react for 2h, add ice water to quench, stir and filter. The filter cake was dissolved with ethyl acetate, wa...

Embodiment 2 9

[0026] Example 2 Synthetic Preparation of Jiulixiang Ketone-II

[0027] Step A: Dissolve 19.6 g (0.1 mol) of 2,6-dimethoxyphenylacetic acid in 200 ml of anhydrous CH 2 Cl 2 Add 9.3ml (0.1mol) BBr dropwise under stirring at -35°C 3 , after the dropwise addition, the reaction temperature was raised to room temperature, stirred overnight, and quenched by adding ice water after 11 hours of reaction, and the water phase was decomposed with CH 2 Cl 2 Extract three times, combine the organic phases, distill off the CH 2 Cl 2 , 9.7 g of 2-hydroxy-6-methoxyphenylacetic acid could be obtained by column chromatography (yield: 53.6%). used directly in the next reaction.

[0028] Step B: Mix 9.1g (0.05mol) of 2-hydroxy-6-methoxyphenylacetic acid with 10.0ml (0.1mol) ethyl propiolate, add 6.8g of anhydrous tin tetrachloride under stirring, and heat To 95°C, react for 1.5h, add ice water to quench, stir and filter. The filter cake was dissolved in ethyl acetate, washed with 1mol / L HC...

Embodiment 3 9

[0031] Example 3 Synthetic Preparation of Jiulixiang Ketone-III

[0032] Step A: Dissolve 19.6 g (0.1 mol) of 2,6-dimethoxyphenylacetic acid in 200 ml of anhydrous CH 2 Cl 2 9.3ml (0.1mol) BBr was added dropwise under stirring at -30°C 3 , after the dropwise addition, the reaction temperature was raised to room temperature, stirred overnight, and quenched by adding ice water after 10 hours of reaction, and the water phase was decomposed with CH 2 Cl 2 Extract three times, combine the organic phases, distill off the CH 2 Cl 2 , 10.8 g (yield: 59.5%) of 2-hydroxy-6-methoxyphenylacetic acid could be obtained by column chromatography. used directly in the next reaction.

[0033] Step B: Mix 9.1g (0.05mol) of 2-hydroxy-6-methoxyphenylacetic acid with 17.5ml (0.175mol) of ethyl propiolate, add 6.8g of anhydrous zinc chloride under stirring, and heat to 100°C, react for 2h, add ice water to quench, stir and filter. The filter cake was dissolved in ethyl acetate, washed with 1...

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Abstract

The invention relates to the technical field of pharmaceuticals, in particular to a novel synthesis method of murrayone and novel application of murrayone in the preparation of drugs for preventing and treating osteoarthritis. The novel synthesis method of murrayone comprises the following steps: reacting 2,6-dimethoxyphenylacetic acid with boron tribromide to prepare 2-hydroxy-6-methoxyphenylacetic acid; reacting the 2-hydroxy-6-methoxyphenylacetic acid with ethyl propiolate to prepare 7-methoxy-8-acetoxy coumarin; reacting the prepared 7-methoxy-8-acetoxy coumarin with solid phosgene to prepare an acyl chloride compound at first, then adding dimethylamine to prepare 7-methoxy-8-(N,N-dimethyl acetamido) coumarin; and reacting the prepared 7-methoxy-8-(N,N-dimethyl acetamido) coumarin with a Grignard reagent such as isopropenyl magnesium bromide to prepare murrayone. Compared with the prior art, the required raw materials are easily accessible, the reaction conditions are mild, and the operation is simple.

Description

technical field [0001] The invention relates to the technical field of medicines, in particular to a new synthesis method of jiulixiangone and its new application in the preparation of medicines for preventing and treating osteoarthritis. Background technique [0002] The chemical name of murrayone (murrayone) is 7-methoxy-8-(3-methyl-3-enyl-2-oxobutyl)benzopyran, which is a simple coumarin compound. Its structure is as follows: [0003] [0004] Jiulixiang ketone is a natural coumarin compound, which is one of the main components of traditional Chinese medicinal materials Jiulixiang and Thianixiang. Jiulixiang ketone is also one of the main medicinal substances in the traditional Chinese medicine Jiulixiang in Sanjiuweitai prescription. Jiulixiangone also exhibits significant anti-tumor activity. The patent "Application of Coumarin Compound Jiulixiangone in the Preparation of Antitumor Drugs" (CN101474173A.) discloses that Jiulixiangone is effective in treating leukemi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/16A61K31/37A61P19/02
Inventor 吴龙火张剑曾靖
Owner GANNAN MEDICAL UNIV
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