Passerini three-component adducts as radical scavengers

被引：8

作者：

Wang, Rui ^{[1
]}

Liu, Zai-Qun ^{[1
]}

机构：

[1] Jilin Univ, Coll Chem, Dept Organ Chem, Changchun 130021, Peoples R China

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 50期

关键词：

Passerini-3CR; Ferrocene; Coumarin; Antioxidant; DNA oxidation; Free radical; DNA OXIDATION; SOLVENT-FREE; EFFICIENT SYNTHESIS; REACTION-PRODUCT; UGI; CHEMISTRY; ALDEHYDES; KINETICS; SYSTEM;

D O I：

10.1016/j.tetlet.2015.11.009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Eighteen alpha-acyloxycarboxamides were produced by Passerini three-component reaction (3CR) in order to reveal sterically synergistic effects among various functional groups on the inhibitory properties of alpha-acyloxycarboxamides toward DNA oxidation and radicals. In trapping 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(+center dot)), 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical and in inhibiting 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA, alpha-acyloxycarboxamides with gallic group exhibited significant activities, which can be further enhanced by incorporation of a ferrocenyl group (derived from ferrocenylmethyl isocyanide) at another tip of the molecule. Therefore, a large volume and electron-abundant isocyanide moiety were able to increase the inhibitory effects of phenolic hydroxyl groups derived from carboxylic acid even in a conjugation-free system. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：7028 / 7033

页数：6

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