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Matrine sodium sulfonate and preparation method

A technology of sodium matrine sulfonate and sulfonating agent, which is applied in the field of sodium matrine sulfonate and its preparation, can solve the problems of central nervous system toxicity and side effects, poor water solubility, inhibition, etc., and achieve increased water solubility, low cost, The effect of reducing toxicity

Inactive Publication Date: 2011-07-20
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Modern research has found that Sophora flavescens mainly contains alkaloids and flavonoids, among which alkaloids are mainly matrine and oxymatrine, and also contain trace amounts of sophorcarpine, sophoramine and sophoridine; It has various pharmacological activities such as anti-tumor, anti-arrhythmia, antibacterial, diuretic, anti-asthma, immunosuppressive, etc., but its water solubility is poor, and it has certain toxic and side effects on the central nervous system. died of respiratory paralysis

Method used

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  • Matrine sodium sulfonate and preparation method
  • Matrine sodium sulfonate and preparation method
  • Matrine sodium sulfonate and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1, the preparation of sodium matrine sulfonate

[0023] Weigh 10g of sophocarpine, add 70mL of water to dissolve it, heat up to 80°C, slowly add the sulfonating agent sodium bisulfite under stirring condition according to the molar ratio of sophocarpine and sulfonating agent of 1:1, and control the temperature at 80°C Under reduced pressure and reflux reaction, the reaction process was monitored by thin layer chromatography (TLC). After 12 hours, the reaction was completed, and the unreacted sophocarpine was extracted with chloroform, the chloroform extract was discarded, the water layer was collected, filtered, and the filtrate was concentrated under reduced pressure. To dryness, the residue was recrystallized with ethanol and dried to obtain sodium matrine sulfonate with a yield of 85.6%.

Embodiment 2

[0024] Embodiment 2, the preparation of sodium matrine sulfonate

[0025] Weigh 10g of sophocarpine, add 70mL of water to dissolve it, heat up to 60°C, slowly add the sulfonating agent sodium bisulfite under stirring condition according to the molar ratio of sophocarpine to sulfonating agent of 1:2, and control the temperature at 60°C Under reduced pressure and reflux reaction, the reaction progress was monitored by TLC method. After 12 hours, the reaction was completed. The unreacted sophocarpine was extracted with chloroform, the chloroform extract was discarded, the water layer was collected, filtered, the filtrate was concentrated to dryness under reduced pressure, and the residue Recrystallize with a mixed solvent of ethanol and ethyl acetate, and dry to obtain sodium matrine sulfonate with a yield of 84%.

Embodiment 3

[0026] Embodiment 3, the preparation of sodium matrine sulfonate

[0027] Weigh 10g of sophocarpine, add 70mL of water to dissolve it, heat up to 40°C, slowly add the sulfonating agent sodium bisulfite under stirring condition according to the molar ratio of sophocarpine to sulfonating agent of 1:3, and control the temperature at 40°C Under reduced pressure and reflux reaction, the reaction process was monitored by TLC. After 12 hours, the reaction was completed, and the unreacted sophocarpine was extracted with ethyl acetate, the ethyl acetate extract was discarded, the water layer was collected, filtered, and the filtrate was concentrated under reduced pressure to After drying, the residue was recrystallized with a mixed solvent of ethanol and acetone, and dried to obtain sodium matrine sulfonate with a yield of 84.7%.

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Abstract

The invention discloses a matrine sodium sulfonate and preparation method thereof. Structural formula of matrine sodium sulfonate is as follows: there are two preparation methods: one is reflux reaction of sophocarpine and sulfonating agent in solvent at 25 DEG. C to 80 DEG. C to prepare matrine sodium sulfonate; the other one is reflux reaction of 13-chloro-matrine or 13-bromo-matrine and sulfonating agent in solvent at 25 DEG. C to 80 DEG. C to prepare matrine-13-sulfoacid which is reacted with salt forming agent o form sodium salt to prepare matrine sodium sulfonate; compared with matrine,water-solubility of matrine sodium sulfonate is enhanced obviously and toxicity is reduced greatly. The preparation method is simple; reaction condition is mild; cost is low and yield is higher, whichis suitable for industrialized production and has greater development prospects in the drug domain.

Description

technical field [0001] The invention relates to a compound and a preparation method thereof, in particular to sodium matrine sulfonate and a preparation method thereof. Background technique [0002] Sophora flavescens is the dried root of the leguminous plant Sophora flavescens Ait.; bitter in taste, cold in nature; Guixin, liver, stomach, large intestine, and bladder meridian; has the effects of clearing away heat and dampness, killing insects, and diuresis; used for dysentery, Hematochezia, jaundice and urinary retention, red and white vaginal discharge, pruritus vulvae, eczema, eczema, itchy skin, mange and leprosy, etc. Modern research has found that Sophora flavescens mainly contains alkaloids and flavonoids, among which alkaloids are mainly matrine and oxymatrine, and also contain trace amounts of sophorcarpine, sophoramine and sophoridine; It has various pharmacological activities such as anti-tumor, anti-arrhythmia, antibacterial, diuretic, anti-asthma, immunosuppre...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/22
Inventor 李逐波廖丹丹赵晨光左华何小燕邓莉陈敏刘青旺田霄杨俊峰
Owner SOUTHWEST UNIV
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