Danshensu derivative, preparation method thereof, and application thereof in pharmacy

A technology of danshensu derivatives and reaction, which is applied in the field of synthesis of danshensu derivatives, can solve problems such as inappropriate chiral resolution, and achieve the effects of reducing leakage rate, increasing SOD activity, and reducing MDA

Inactive Publication Date: 2009-12-23
FUDAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since there are two phenolic hydroxyl groups that are easily oxidized in the structure of Danshensu, it is not suitable to use the direct resolution method to perform chiral resolution of Danshensu racemate to obtain natural D-danshensu

Method used

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  • Danshensu derivative, preparation method thereof, and application thereof in pharmacy
  • Danshensu derivative, preparation method thereof, and application thereof in pharmacy
  • Danshensu derivative, preparation method thereof, and application thereof in pharmacy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] According to the following reaction scheme, prepare 2-acetoxy-3-(6-nitro-3,4-methylenedioxophenyl)propionic acid (1):

[0025]

[0026] Take raw material 3,4-methylene oxyphenyl lactic acid 0.5g, 2.4mmol dissolved in 6mL acetic acid and 1.5mL acetic anhydride mixture, put in ice bath, 1 drop of concentrated nitric acid, 21 drops of acetic acid, 21 drops of acetic anhydride Prepare a mixed solution, slowly drop it into the reaction solution, react in an ice-water bath for 4 hours, use petroleum ether / ethyl acetate / acetic acid (V / V / V) = 15:15:3 as the developer, and display under TLC ultraviolet light Raw materials (R f =0.5), the main product point in the reaction solution (R f =0.5), the raw material can be roasted brown after soaking in phosphomolybdic acid, and the two products are baked light yellow, stop the reaction, add 15mL water, extract with ethyl acetate, wash the extract with water 3 times, dry over anhydrous magnesium sulfate, Mix crude silica gel, sepa...

Embodiment 2

[0027] Example 2 Preparation of 2-hydroxyl-3-(6-nitro-3,4-methylenedioxophenyl) propionic acid (2)

[0028] Mix 1mL of concentrated nitric acid and 1.4mL of concentrated sulfuric acid to make a mixed acid solution, put it in an ice-water bath, dissolve 0.2g, 0.95mmol of raw material 3,4-methylene oxide phenyl lactic acid in 1mL of acetone, slowly drop into the mixed acid under stirring , yellow smoke was emitted during the dropwise addition process, stirred and reacted in an ice-water bath for 10 minutes, using petroleum ether / ethyl acetate / acetic acid (V / V / V)=10:10:2 as the developer, TLC showed that the raw material (R f =0.7), there are two product points in the reaction solution (R f =0.5, 0.3), stop the reaction, pour the reaction solution into 20mL water, extract with ethyl acetate, dry the extract, filter the desiccant, mix with crude silica gel, separate and purify by column chromatography, the eluent is petroleum ether / ethyl acetate Ester / acetic acid (V / V / V)=60:20:1,...

Embodiment 3

[0030] Example 3 Experiments on Danshensu Derivatives' Protective Effect on Ischemic Myocardium

[0031] Cardiomyocyte hypoxia model was established by primary culture of neonatal rat cardiomyocytes according to conventional methods. The experiment was divided into normal control group: no drug intervention, no hypoxia and glucose deficiency, model group: no drug intervention, hypoxia and glucose deficiency for 5 hours, medication group: drug administration for 10 hours -8 mol / L, 10 -7 mol / L, 10 -6 mol / L, hypoxia and glucose deficiency.

[0032] The experimental results show that the intracellular LDH of the normal control group is 100%, and the difference between the intracellular LDH of each medication group and the hypoxia group and the normal control group is the LDH leakage rate. Compared with the hypoxia group, the compound of the present invention can reduce the hypoxia Cardiomyocyte LDH leakage rate ( figure 1); Compared with the hypoxic group, the compound of the...

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Abstract

The invention belongs to the field of medicament synthesis, and relates to a Danshensu derivative. The Danshensu derivative with a stable structure as above is obtained by combining Danshensu analogue and nitryl. By culturing primary rat cardiocytes, establishing a hypoxia model of cardiocytes and acute and chronic rat models of myocardial infarction, and performing pharmacological tests in vivo and in vitro, results show that the compound has good effect of protecting hypoxic cardiac muscle and certain anti-HIV activity. The compound can be taken as a pilot compound of original innovative medicaments for resisting myocardial ischemia to further prepare medicaments for treating ischemic heart disease and medicaments with anti-HIV activity.

Description

technical field [0001] The invention belongs to the field of medicine synthesis, and relates to a synthesis method of a danshensu derivative and an application in pharmacy. Background technique [0002] Traditional Chinese medicine has a long history in our country and has a history of thousands of years. Its main advantage is that it has less toxic and side effects. Therefore, the preparation of effective monomers of traditional Chinese medicine and the synthesis and semi-synthesis of chemical drugs and salt-forming derivatives using natural active ingredients as lead compounds, that is, the modernization of traditional Chinese medicine, have become the main direction of modern Chinese medicine research. Danshensu (chemical name: D-(+)-β-3,4-dihydroxyphenyl lactic acid) is a main active ingredient in the traditional Chinese medicine Salvia miltiorrhiza, a variety of traditional Chinese medicine compound preparations with Danshensu as the main component, such as compound sal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/62C07C205/56A61K31/36A61K31/192A61P9/10A61P31/18
Inventor 朱依谆王洋董村南
Owner FUDAN UNIV
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