O-nitro caffeic acid phenethyl ester, preparation method and application thereof

A technology of caffeic acid phenethyl ester and nitrocaffeic acid, which is applied in the field of caffeic acid phenethyl ester derivatives and its preparation, can solve the problems of damage to the integrity of cell membranes and organelle membranes, expansion of infarct area, and low contractile function, and achieve The effect of maintaining antioxidant capacity, fast synthesis speed, and easy operation

Inactive Publication Date: 2016-06-15
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Persistent myocardial ischemia leads to tissue damage and cell death. Early reperfusion can reduce the degree of myocardial ischemia damage, but after reperfusion improves myocardial blood supply, it also aggravates the damage caused by simple myocardial ischemia, and is prone to arrhythmia , infarct size expansion, persistent ventricular systolic dysfunction and other conditions, pathological changes may include myocardial cell edema, damage to the integrity of cell membranes and organelle membranes, destructive rupture of muscle fibers, ultrastructural changes, microvascular injury and no reperfusion, etc.

Method used

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  • O-nitro caffeic acid phenethyl ester, preparation method and application thereof
  • O-nitro caffeic acid phenethyl ester, preparation method and application thereof
  • O-nitro caffeic acid phenethyl ester, preparation method and application thereof

Examples

Experimental program
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Effect test

preparation example 1

[0027] Preparation example 1. Preparation of phenethyl o-nitrocaffeate (the acylation step uses dichloromethane as a solvent)

[0028] Put 0.9g (5.0mmol) of caffeic acid and 0.4ml (5.6mmol) of thionyl chloride into a 100ml round-bottomed flask, add 20ml of anhydrous dichloromethane to dissolve, heat up to 100°C for reflux reaction, and monitor with thin-layer chromatography Reaction process, after the reaction is completed, cool down to room temperature, add dropwise 20ml of dichloromethane solution of 0.8g (4.8mmol) of o-nitrophenylethanol, mix well, then add dropwise 0.2ml (1.4mmol) of triethylamine, and heat up to Reflux reaction at 50°C, and monitor the reaction process by thin-layer chromatography. After the reaction is completed, distill the reaction liquid under reduced pressure to remove the solvent to obtain a yellow-brown liquid. After dissolving with an appropriate amount of anhydrous acetone, add 80-100 mesh silica gel and stir to After the acetone was distilled ...

preparation example 2

[0029] Preparation example 2. Preparation of phenethyl o-nitrocaffeate (acylation step uses thionyl chloride as solvent)

[0030] Put 0.9g (5.0mmol) of caffeic acid and 20ml of thionyl chloride into a 100ml round bottom flask, mix well, heat up to 100°C for reflux reaction, and after the reaction solution becomes clear, distill off the remaining thionyl chloride under reduced pressure To obtain milky white solid caffeic acid chloride, add 20ml of anhydrous dichloromethane (dried with calcium hydride) to dissolve, add 0.8g (4.8mmol) of o-nitrophenylethanol 20ml of dichloromethane solution dropwise at room temperature, and mix well , then added 0.3ml (2.2mmol) of triethylamine dropwise, raised the temperature to 50°C for reflux reaction, and monitored the reaction process by thin-layer chromatography. After an appropriate amount of anhydrous acetone is dissolved, add 80-100 mesh silica gel to stir and mix evenly, and then distill off the acetone under reduced pressure, then us...

preparation example 3

[0031] Preparation example 3. Preparation of phenethyl o-nitrocaffeic acid (acylation step uses thionyl chloride as solvent, increasing catalyst consumption)

[0032] Put 0.9g (5.0mmol) of caffeic acid and 20ml of thionyl chloride into a 100ml round bottom flask, mix well, heat up to 100°C for reflux reaction, and after the reaction solution becomes clear, distill off the remaining thionyl chloride under reduced pressure To obtain milky white solid caffeic acid chloride, add 20ml of anhydrous dichloromethane (dried with calcium hydride) to dissolve, add 0.8g (4.8mmol) of o-nitrophenylethanol 20ml of dichloromethane solution dropwise at room temperature, and mix well , then added 0.4ml (2.9mmol) of triethylamine dropwise, raised the temperature to 50°C for reflux reaction, and monitored the reaction process by thin-layer chromatography. After an appropriate amount of anhydrous acetone is dissolved, add 80-100 mesh silica gel to stir and mix evenly, and then distill off the ac...

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Abstract

The invention discloses o-nitro caffeic acid phenethyl ester with a structural formula shown as formula I. The method includes: subjecting caffeic acid and thionyl chloride to acylation reaction to generate caffeoyl chloride, then in the presence of a catalyst, subjecting the caffeoyl chloride and o-nitrophenylethanol to esterification reaction in an organic solvent, thus obtaining o-nitro caffeic acid phenethyl ester. Compared with caffeic acid phenethyl ester, the o-nitro caffeic acid phenethyl ester has better effect of protecting antioxidant enzyme activity, stronger ability of clearing oxygen free radicals, and better effects of maintaining antioxidant ability of myocardial cells, protecting normal cell structure and alleviating cell oxidative damage, can significantly reduce ischemia/reperfusion myocardial cell apoptosis, decreases myocardial infarction area, can be used for preparation of drugs for improving ischemia reperfusion injury, and plays an important role in treatment of cardiovascular system diseases. (formula I).

Description

Technical field [0001] The present invention is a chemical pharmaceutical field involving a coffee acid benzene -phenyl -hydroxy derivative and its preparation methods and pharmaceutical use. Background technique [0002] In recent years, the incidence and mortality of cardiovascular system diseases have continued to rise, and it has become the number one health killer in the world today.Cardiopathic ischemia re -injection injury (IRI) is a hot issue for cardiovascular research.Copycin -myocardial ischemia leads to tissue injury and cell death. Early irrigation can reduce the degree of damage to myocardial ischemia.The infarction area is enlarged and the durable ventricular contraction function is low. Pathological changes can occur in myocardial cell edema, cell membrane and cellular membrane integrity destruction, muscle fiber destructive fracture ultra -micro structure, microvascular injury, and no reperfusion phenomenon.Condition ischemia re -injection damage is the main fact...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/42A61P39/06A61P9/00A61P9/10
CPCC07C51/60C07C201/12C07C205/42C07C59/52
Inventor 李逐波李德娟左华何小燕
Owner SOUTHWEST UNIVERSITY
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