Preparation and antioxidant activity of α-pyridoin and its derivatives

Masashi Hatanaka, Kyoko Takahashi, Shigeo Nakamura, Tadahiko Mashino

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)6763-6770
Number of pages8
JournalBioorganic and Medicinal Chemistry
Volume13
Issue number24
DOIs
Publication statusPublished - 2005 Dec 15

Fingerprint

Antioxidants
Scavenging
Derivatives
Lipid Peroxidation
Assays
Pyridines
Lead compounds
Lipids
tert-Butylhydroperoxide
Liver Microsomes
Liver
Ascorbic Acid
Carrier concentration
Rats
Electrons
Oxidation
2,2-diphenyl-1-picrylhydrazyl
2,2'-pyridoin
Lead

Keywords

  • α-Pyridoin
  • Antioxidant
  • Enediol
  • Radical scavenger

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Preparation and antioxidant activity of α-pyridoin and its derivatives. / Hatanaka, Masashi; Takahashi, Kyoko; Nakamura, Shigeo; Mashino, Tadahiko.

In: Bioorganic and Medicinal Chemistry, Vol. 13, No. 24, 15.12.2005, p. 6763-6770.

Research output: Contribution to journalArticle

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