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4-alkoxy-coumarin fatty acid ester, synthetic method and use

A technology of fatty acid ester and synthesis method, which is applied in the direction of drug combination, carboxylic acid halide preparation, metabolic diseases, etc., to achieve safe analgesia and weight loss drugs, and less stimulating effects such as spicy taste

Inactive Publication Date: 2011-02-09
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004]The research results show that the analgesic and weight-loss effect of coumarin fatty acid ester (capsaicin) is lower than that of capsaicin, and still has a weak stimulating effect such as spicy taste

Method used

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  • 4-alkoxy-coumarin fatty acid ester, synthetic method and use
  • 4-alkoxy-coumarin fatty acid ester, synthetic method and use
  • 4-alkoxy-coumarin fatty acid ester, synthetic method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Embodiment 1: Preparation of 4-ethoxyl-coumarin caprate

[0059] ①. Under nitrogen protection, dehydrated dimethyl sulfoxide (DMSO) 5.0ml, Cs 2 CO 3 (0.1mmol), K 2 CO 3 (2.0mmol), vanillyl alcohol (1.0mmol) and ethyl bromide (1.2mmol) were sequentially added into a round bottom flask, and the reaction was stirred at room temperature for 15h.

[0060] ② After the reaction is completed, add 100ml of isopropyl ether to dilute, then filter the contents of the flask, wash with water, and wash with anhydrous Na 2 SO 4 dry. After the solvent was removed, it was purified by silica gel column chromatography (petroleum ether / ethyl acetate=5:2) to obtain a colorless oily liquid, which was the 4-ethoxy-coumarin intermediate.

[0061] ③. Under nitrogen protection, dissolve 0.5mmol of 4-ethoxy-coumarin intermediate in 8ml of anhydrous tetrahydrofuran, then add 0.5mmol of decanoyl chloride, 0.081mmol of SbCl 3 , Stir the reaction at room temperature for 12h.

[0062] ④, after ...

Embodiment 2

[0064] Embodiment 2: Preparation of 4-octanyloxy-coumarin caprate

[0065] ①. Under nitrogen protection, dehydrated dimethyl sulfoxide (DMSO) 5.0ml, Cs 2 CO 3 (0.1mmol), K 2 CO 3 (2.0mmol), vanillyl alcohol (1.0mmol) and bromooctane (1.2mmol) were sequentially added into a round bottom flask, and the reaction was stirred at room temperature for 15h.

[0066] ② After the reaction is completed, add 100ml of isopropyl ether to dilute, then filter the contents of the flask, wash with water, and wash with anhydrous Na 2 SO 4 dry. After the solvent was removed, it was purified by silica gel column chromatography (petroleum ether / ethyl acetate=5:2) to obtain a colorless oily liquid, namely 4-octanyloxy-coumarin intermediate.

[0067] ③. Under nitrogen protection, dissolve 0.5mmol of 4-octyloxy-coumarin intermediate in 8ml of anhydrous tetrahydrofuran, then add 0.5mmol of decanoyl chloride, 0.081mmol of SbCl 3 , Stir the reaction at room temperature for 12h.

[0068] ④, after ...

Embodiment 3

[0070] Embodiment 3: Preparation of 4-tetradecyloxy-coumarin caprate

[0071] ①. Under nitrogen protection, dehydrated dimethyl sulfoxide (DMSO) 5.0ml, Cs 2 CO 3 (0.1mmol), K 2 CO 3 (2.0mmol), vanillyl alcohol (1.0mmol) and tetradecane bromide (1.2mmol) were sequentially added into a round bottom flask, and the reaction was stirred at room temperature for 15h.

[0072] ② After the reaction is completed, add 100ml of isopropyl ether to dilute, then filter the contents of the flask, wash with water, and wash with anhydrous Na 2 SO 4 dry. After the solvent was removed, it was purified by silica gel column chromatography (petroleum ether / ethyl acetate=5:2) to obtain a colorless oily liquid, which was the 4-tetradecyloxy-coumarin intermediate.

[0073] ③. Under nitrogen protection, dissolve 0.5mmol of 4-tetradecyloxy-coumarin intermediate in 8ml of anhydrous tetrahydrofuran, then add 0.5mmol of decanoyl chloride, 0.081mmol of SbCl3 , Stir the reaction at room temperature for ...

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Abstract

The invention relates to a novel chemical substance. The chemical name of the substance is 4-alkoxyl-coumarin fatty acid ester, and the molecular structural formula is shown as the graph. Differed from capsaicine, the novel chemical substance does not have any stimulatory effect, and has analgesic function and weight-reducing function similar to the capsaicine. Therefore, the novel chemical substance is a novel compound which has good market prospect and high medicinal value in pain relief and weight reducing.

Description

technical field [0001] The present invention relates to a new compound, in particular to a derivative of coumarin fatty acid ester. Background technique [0002] Capsaicin (capsaicin) is an extremely pungent vanilla amide alkaloid extracted from red pepper, which has various biological activities such as weight loss (reference 1) and analgesia (reference 2). It has been included in the 24th edition of the United States Pharmacopoeia, and is widely used in the treatment of arthritis, muscle pain, back pain, sports sprains and residual neuralgia after herpes zoster. "Drug Evaluation" edited by the American Medical Association (AMA) also included it as the drug of choice for the treatment of postherpetic neuralgia and diabetic neuralgia. [0003] Yet the pungent taste that capsaicin has and the pain that it produces severely limit its application in the field of medicine and health care, therefore, there is no pungent taste and capsicum esters (coumarin fatty acid esters) wit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/025C07C67/14A61K31/222A61P29/00A61P3/04
Inventor 叶小利李学刚袁吕江
Owner SOUTHWEST UNIV
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