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Application of free radical of nitroxide to treatment of ischemia reperfusion injury

A technology of ischemia-reperfusion and selection, which is applied in the field of medicine and can solve the problems of large clinical gaps

Inactive Publication Date: 2013-11-20
FOURTH MILITARY MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There is currently no effective treatment for multi-tissue and multi-organ damage caused by ischemia, and there is a large clinical gap

Method used

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  • Application of free radical of nitroxide to treatment of ischemia reperfusion injury
  • Application of free radical of nitroxide to treatment of ischemia reperfusion injury
  • Application of free radical of nitroxide to treatment of ischemia reperfusion injury

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Embodiment 1: the synthetic method of compound 1

[0017]

[0018] (1) Synthesis of 4-hydroxyphenylacrylic acid chloride

[0019] Dissolve 1.64 g (10.0 mmol) p-hydroxyphenylacrylic acid in 50 mL CH 2 Cl 2 , cooled in an ice-water bath, and added dropwise 10.0 mL SOCl 2 (1.18 g) CH 2 Cl 2 solution, and then warmed to reflux for 2h to stop the reaction. The solvent was removed under reduced pressure and used directly in the next reaction.

[0020] (2) Synthesis of p-hydroxyl nitroxide free radicals

[0021] 1.22 g (10.0 mmol) of p-hydroxybenzaldehyde and 1.48 g (10.0 mmol) of dihydroxylamine were dissolved in 50 mL of methanol and refluxed for 24 h. A large amount of white insoluble matter was formed, filtered, and the filter cake was washed with a small amount of methanol. Suspend the filter cake in 50.0 mL CH 2 Cl 2 , cooled in an ice-water bath, and added 30.0 mL NaIO 4 (1.7 g) aqueous solution, the reaction was stopped after stirring for 15 min. Af...

Embodiment 2

[0024] Embodiment 2: the synthetic method of compound 2

[0025]

[0026] (1) Synthesis of 3-methoxy-4-hydroxyphenylacrylic acid chloride

[0027] Dissolve 1.94 g (10.0 mmol) p-hydroxyphenylacrylic acid in 50 mL CH 2 Cl 2 , cooled in an ice-water bath, and added dropwise 10.0 mL SOCl 2 (1.18 g) CH 2 Cl 2 solution, and then warmed to reflux for 2h to stop the reaction. The solvent was removed under reduced pressure for the next reaction.

[0028] (2) compound 2 Synthesis

[0029] Dissolve 2.49 g (10.0 mmol) of p-hydroxyl nitroxide in 50 mL CH 2 Cl 2 , cooled in an ice-water bath, and added dropwise 2.12 g (10.0 mmol) of 3-methoxy-4-hydroxyphenylacrylic acid chloride in 20.0 mL of CH 2 Cl 2 solution, and then warmed to reflux for 2h to stop the reaction. The solvent was removed under reduced pressure, and the product was purified by column chromatography to obtain 3.91 g of the product, with a yield of 92%. mp: 245~247℃. IR ( ν max / cm -1 ): 3485, 1720, 16...

Embodiment 3

[0030] Embodiment 3: the synthetic method of compound 3

[0031]

[0032] (1) Synthesis of 3-hydroxy-4-hydroxybenzeneacrylic acid chloride

[0033] Dissolve 1.64 g (10.0 mmol) p-hydroxyphenylacrylic acid in 50 mL CH 2 Cl 2 , cooled in an ice-water bath, and added dropwise 10.0 mL SOCl 2 (1.18 g) CH 2 Cl 2 solution, and then warmed to reflux for 2h to stop the reaction. The solvent was removed under reduced pressure for the next reaction.

[0034] (2) compound 3 Synthesis

[0035] Dissolve 2.49 g (10.0 mmol) of p-hydroxyl nitroxide in 50 mL CH 2 Cl 2 , cooled in an ice-water bath, and added dropwise 1.98 g (10.0 mmol) of p-hydroxybenzoic acid chloride in 20.0 mL of CH 2 Cl 2 solution, and then warmed to reflux for 2h to stop the reaction. The solvent was removed under reduced pressure, and the product was purified by column chromatography to obtain 3.91 g of the product, with a yield of 95%. mp: 203~204℃. IR ( ν max / cm -1 ): 3480, 1710, 1647, 1509, 1635,...

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PUM

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Abstract

The invention discloses a compound as shown in the structural general formula (I), wherein R is a substituent or double substituents and is independently selected from NO2, OH, OCH3, halogen and H. The compound is used for treating ischemia reperfusion injury. The compound is simple and convenient in synthesis method; and a molecule of the compound contains a structural unit of the free radical of nitroxide to ensure that free radical can be removed efficiently and circularly, and the compound has a remarkable inhibiting effect on ischemia reperfusion injury, so that the compound has important practical values.

Description

technical field [0001] The invention relates to the application of a class of novel nitroxide free radicals in the treatment of ischemia-reperfusion injury, and belongs to the technical field of medicine. Background technique [0002] Tissue damage caused by ischemia is the main cause of fatal diseases, such as myocardial infarction, stroke, liver and kidney ischemia caused by coronary artery sclerosis, which has the characteristics of high morbidity, high mortality and high disability rate, serious It threatens human health and brings huge burden to society, government and family. [0003] There is currently no effective treatment for multi-tissue and multi-organ damage caused by ischemia, and there is a large clinical gap. Therefore, the research and development of new drugs that can effectively prevent or alleviate ischemia-reperfusion injury has become an important task for pharmaceutical workers in my country and even in the world, and it is also one of the important p...

Claims

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Application Information

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IPC IPC(8): C07D233/22A61P9/10A61P39/06
Inventor 王海波孙晓莉高鹏贾玉晶
Owner FOURTH MILITARY MEDICAL UNIVERSITY
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