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Method for synthesizing (+/-)-Murracarpin and anti-inflammatory and analgesic effect thereof

A synthetic method and technology of acetone, applied in the direction of anti-inflammatory agents, medical preparations containing active ingredients, drug combinations, etc., can solve the problems of no anti-inflammatory and analgesic activity, etc., and achieve easy-to-obtain raw materials, simple implementation and operation, The effect of mild reaction conditions

Inactive Publication Date: 2010-09-08
许瑞安
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, there has been no report on the chemical synthesis of (±)-murracarpin, nor has there been any report on the anti-inflammatory and analgesic activity of (±)-murracarpin

Method used

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  • Method for synthesizing (+/-)-Murracarpin and anti-inflammatory and analgesic effect thereof
  • Method for synthesizing (+/-)-Murracarpin and anti-inflammatory and analgesic effect thereof
  • Method for synthesizing (+/-)-Murracarpin and anti-inflammatory and analgesic effect thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] (±)-Murracarpin Synthetic Preparation-I

[0042]Step A: Dissolve 8.1 g (50 mmol) of 7-hydroxycoumarin and 20 ml of acetic anhydride in 100 ml of anhydrous acetone, and slowly add 2 ml of pyridine dropwise. After reacting for 1 h at room temperature, a large amount of white precipitate was observed by adding an equal volume of water. The entire reaction system was washed with 10 times the volume of distilled water, and the collected precipitate was 9.73 g (95%) of 7-acetoxycoumarin. used directly in the next reaction.

[0043] Step B: Add 7.5g (37mmol) of 7-acetoxycoumarin to 50ml of trifluoroacetic acid under ice-cooling, and add 7.5g (53.5mmol) of hexamethylenetetramine under vigorous stirring. After cooling to room temperature, start heating to 88°C, and reflux for 8h. Evaporate excess trifluoroacetic acid, add 30ml of distilled water, continue to stir at 60°C for 30min, and a large amount of white precipitate can be seen. Cool to 0°C, collect by filtration and w...

Embodiment 2

[0048] (±)-Murracarpin Synthetic Preparation-II

[0049] Step A: Dissolve 8.1 g (50 mmol) of 7-hydroxycoumarin and 30 ml of acetic anhydride in 120 ml of anhydrous acetone, and slowly add 3 ml of pyridine dropwise. After reacting for 1 h at room temperature, a large amount of white precipitate was observed by adding an equal volume of water. The entire reaction system was washed with 10 times the volume of distilled water, and the collected precipitate was 9.75 g (96%) of 7-acetoxycoumarin. used directly in the next reaction.

[0050] Step B: Add 7.5g (37mmol) of 7-acetoxycoumarin to 40ml of trifluoroacetic acid under ice-cooling, and add 7.5g (53.5mmol) of hexamethylenetetramine under vigorous stirring. After cooling to room temperature, began heating to 90 ° C, reflux 11h. Evaporate excess trifluoroacetic acid, add 30ml of distilled water, continue to stir at 60°C for 30min, and a large amount of white precipitate can be seen. Cool to 0°C, collect by filtration and wash...

Embodiment 3

[0055] Effects of Different Compounds on the Inhibition Rate of Mouse Ear Swelling Caused by Xylene

[0056] Experimental method reference: Chen YF, Tsai HY, Wu TS. Anti-inflammatory and analgesic activities from roots of Angelica pubescens[J].Planta-Med.1995.61(1), 2-8.

[0057] Take (±)-murracarpin, osthole, and umbelliferin, dissolve them in 1% Tween-80 solution, dissolve them by ultrasonic, and prepare them at a concentration of 10 mg / kg. The positive control group was given 0.5mg / kg dexamethasone.

[0058] There were 6 rats in each group, fasted for 18-22 hours before the experiment, without water. The administration group was given each compound by intraperitoneal injection (ig). The positive group ig dexamethasone 0.5mg / kg, the blank control group was given the same volume of normal saline, continuous administration for 7 days, 1 hour after the last administration, 30 μl of xylene was evenly applied to the front and back of the right ear of the mouse, and the left ea...

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Abstract

The invention relates to the field of natural medicinal chemistry, in particular to a method for synthesizing (+ / -)-Murracarpin and anti-inflammatory and analgesic effect thereof. The method for preparing the (+ / -)-Murracarpin comprises the following steps of: reacting 7-hydroxy coumarin, acetic anhydride, trifluoroacetic acid and hexamethylenetetramine to obtain 7-hydroxy-8-formoxyl coumarin; reacting the 7-hydroxy-8-formoxyl coumarin with (Me)2SO4 to obtain 7-methoxy-8-formoxyl coumarin; reacting the obtained 7-methoxy-8-formoxyl coumarin with 1-chloroacetone to obtain 8-(2'-acetyl epoxy ethyl)-7-methoxy coumarin, and reacting the 8-(2'-acetyl epoxy ethyl)-7-methoxy coumarin, methyltriphenyl phosphorous bromide and LDA to obtain 8-(2'-propenyl epoxy ethyl)-7-methoxy coumarin; and performing acid hydrolysis on the obtained 8-(2'-propenyl epoxy ethyl)-7-methoxy coumarin in methanol to obtain the (+ / -)-Murracarpin. Research shows that the obtained compound has anti-inflammatory and analgesic effect.

Description

Technical field: [0001] The invention relates to a chemical synthesis method of a natural coumarin compound; the invention also relates to a new application of the compound for anti-inflammation and analgesia. Background technique: [0002] The chemical name of (±)-Murracarpin is (±)-8-(1'-methoxy-2'-hydroxy-3'-methyl-1'-butenyl)-7-methoxybenzopyran , is a simple coumarin compound whose structure is shown below: [0003] [0004] (±)-Murracarpin is a natural coumarin compound, which is one of the main components of the traditional Chinese medicine Murracarpin. Scientists have isolated and identified this compound (Dananhar MD, Indian J Chem Ser19B, 1980, 1006-1008; Wu TS, Phytochemistry, 1989, 28(1): 293-294). According to ancient records of traditional Chinese medicine, murris has anti-inflammatory and analgesic effects, but there is no research report on the biological activities of coumarin compounds such as anti-inflammatory and analgesic effects. In our laboratory...

Claims

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Application Information

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IPC IPC(8): C07D311/18A61K31/352A61P29/00
Inventor 许瑞安吴龙火
Owner 许瑞安
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