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Phenylethyl o-nitrocaffeate and its preparation method and application

A technology of nitrocaffeic acid and phenethyl ester, which is applied in the preparation of carboxylates, chemical instruments and methods, and the preparation of organic compounds. It can solve the problems of damage to the integrity of cell membranes and organelle membranes, low systolic function, and myocardial cell edema. problem, to achieve the effect of maintaining antioxidant capacity, easy operation, and fast synthesis speed

Inactive Publication Date: 2018-04-13
SOUTHWEST UNIV
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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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  • Phenylethyl o-nitrocaffeate and its preparation method and application
  • Phenylethyl o-nitrocaffeate and its preparation method and application
  • Phenylethyl o-nitrocaffeate and its preparation method and application

Examples

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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 of...

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 use ...

preparation example 3

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

[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 invention belongs to the field of chemical pharmacy, and relates to a phenethyl caffeic acid derivative, a preparation method and a pharmaceutical use thereof. Background technique [0002] In recent years, the morbidity and mortality of cardiovascular system diseases have been rising, and they have become the number one health killer in the world today. Myocardial ischemia-reperfusion injury (ischemia reperfusion injury, IRI) is a hot issue in cardiovascular research. 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 o...

Claims

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Application Information

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Patent Type & Authority Patents(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 UNIV
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