Substituent Effects on Reactive Oxygen Species (ROS) Generation by Hydroquinones

被引：10

作者：

Dharmaraja, Allimuthu T. ^{[1
]}

Jain, Charu ^{[1
]}

Chakrapani, Harinath ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res Pune, Dept Chem, Pune 411021, Maharashtra, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 19期

关键词：

HYDROGEN-PEROXIDE; CELL-DEATH; BACTERICIDAL ANTIBIOTICS; XANTHINE-OXIDASE; BETA-DIKETONES; SMALL-MOLECULE; CANCER; INHIBITORS; CHEMISTRY; MECHANISM;

D O I：

10.1021/jo501796z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In order to understand the structural aspects of stabilization of hydroquinones and their ability to generate reactive oxygen species (ROS), we designed and synthesized a series of 6-aryl-2,3-dihydro-1,4-benzoquinones. These compounds equilibrate with the corresponding 6-aryl-1,4-dihydroxybenzenes in an organic medium; a linear free energy relationship analysis gave rho = +2.37, suggesting that this equilibrium was sensitive to electronic effects. The propensity of the compound to enolize appears to determine ROS-generating capability, thus offering scope for tunable ROS generation.

引用

页码：9413 / 9417

页数：5

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