Preparation and antioxidant activity of α-pyridoin and its derivatives

Masashi Hatanaka, Kyoko Takahashi, Shigeo Nakamura, Tadahiko Mashino

研究成果: Article査読

32 被引用数 (Scopus)

抄録

Focusing on α-pyridoin (1, 1,2-di(2-pyridyl)-1,2-ethenediol) as the lead compound of the novel antioxidative enediol, we synthesized 5,5′- or 6,6′-bis-substituted derivatives of 1 from disubstituted pyridines. The antioxidant activity of 1 and its synthetic derivatives 2-7 was evaluated by DPPH (1,1-diphenyl-2-picrylhydrazyl radical) scavenging assay and inhibition of lipid peroxidation. In the DPPH assay, 1 exhibited an activity stronger than that of ascorbic acid, and 5,5′-dimethyl-(5) or 5,5′-dimethoxy- substituted derivatives (6) exhibited more potent activity than 1. The DPPH scavenging activities of α-pyridoins were correlated with their oxidation potential and thus the electron density of enediol. 5 and 6 effectively inhibited lipid peroxidation in the rat liver microsome/tert-butyl hydroperoxide system. Therefore, 5 and 6 serve as good candidates for a pharmacologically useful enediol antioxidant.

本文言語English
ページ(範囲)6763-6770
ページ数8
ジャーナルBioorganic and Medicinal Chemistry
13
24
DOI
出版ステータスPublished - 2005 12月 15

ASJC Scopus subject areas

  • 生化学
  • 分子医療
  • 分子生物学
  • 薬科学
  • 創薬
  • 臨床生化学
  • 有機化学

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