Passerini three-component adducts as radical scavengers
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- 作者：Rui Wang ; Zai-Qun Liu ; zaiqun-liu@jlu.edu.cn" class="auth_mail" title="E-mail the corresponding author
- 关键词：Passerini-3CR ; Ferrocene ; Coumarin ; Antioxidant ; DNA oxidation ; Free radical
- 刊名：Tetrahedron Letters
- 出版年：2015
- 出版时间：16 December 2015
- 年：2015
- 卷：56
- 期：50
- 页码：7028-7033
- 全文大小：608 K
文摘
Eighteen α-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 α-acyloxycarboxamides toward DNA oxidation and radicals. In trapping 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+
), 2,2′-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical and in inhibiting 2,2′-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA, α-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.
), 2,2′-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical and in inhibiting 2,2′-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA, α-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.