5-Aminouracil as Effective Inhibitor of Peroxyl Radicals. Experimental and Theoretical Studies

被引：0

作者：

Grabovskiy, Stanislav A. ^{[1
]}

Konkina, Irina G. ^{[1
]}

Murinov, Yuri I. ^{[1
]}

Kabal'nova, Natalia N. ^{[1
]}

机构：

[1] Russian Acad Sci, Inst Russian Acad Sci, Inst Organ Chem, Ufa Res Ctr, Ufa 450054, Russia

来源：

CURRENT ORGANIC CHEMISTRY | 2012年 / 16卷 / 11期

关键词：

DFT; Uracils; Oxidation; Peroxyl radical; Relative rate constant; ANTIOXIDANT ACTIVITY; RATE-CONSTANT; AUTOXIDATION; PEROXIDATION; DERIVATIVES; FLAVONOIDS; OXIDATION; DAMAGE; ACID;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 5-aminouracil with peroxyl radicals generated by the thermal decomposition of 2,2'-azo-bis(2-methylpropionitrile) (AIBN) and 2,2'-azo-bis(2-amidinopropane) dihydrochloride was studied at 50 degrees C in ethanol and water (pH 7.0) solution respectively. The oxidation product of 5-aminouracil formed by peroxyl radicals was dihydro-5,5,6-trihydroxypyrimidine-2,4-dione. The relative rate constant of 5-aminouracil vs. quercetin and 2,6-di-tert-butyl-4-methylphenol by peroxyl radicals generated from AIBN was measured in ethanol and found to be 0.19 (50 degrees C) and 3.6 (70 degrees C) respectively. Theoretical data of the redox potential and the bound dissociation energy oppose against single electron/proton transfer mechanism and provide support for a hydrogen atom abstraction mechanism. Transition structures and activation barriers of the hydrogen abstraction from 5-aminouracil, 5-hydroxy-6-methyluracil and 2,6-di-tert-butyl-4-methylphenol by methyl peroxyl radical were determined with the BB1K/6-31+G(d,p) level of theory. The relative theoretical reactivity was found to be in a good agreement with the experimental results and also supported the hydrogen abstraction mechanism.

引用

页码：1447 / 1452

页数：6

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