Synthesis and radical-scavenging activity of a dimethyl catechin analogue

Kohei Imai, Ikuo Nakanishi, Akiko Ohno, Masaaki Kurihara, Naoki Miyata, Ken Ichiro Matsumoto, Asao Nakamura, Kiyoshi Fukuhara

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Catechin analogue 1 with methyl substituents ortho to the catechol hydroxyl groups was synthesized to improve the antioxidant ability of (+)-catechin. The synthetic scheme involved a solid acid catalyzed Friedel-Crafts coupling of a cinnamyl alcohol derivative to 3,5-dibenzyloxyphenol followed by hydroxylation and then cyclization through an intermediate orthoester. The antioxidative radical scavenging activity of 1 against galvinoxyl radical, an oxyl radical, was found to be 28-fold more potent than (+)-catechin.

Original languageEnglish
Pages (from-to)2582-2584
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume24
Issue number11
DOIs
Publication statusPublished - 2014 Jun 1

Keywords

  • Antioxidant
  • Catechin
  • Radical scavenging
  • Synthetic antioxidant

ASJC Scopus subject areas

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

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  • Cite this

    Imai, K., Nakanishi, I., Ohno, A., Kurihara, M., Miyata, N., Matsumoto, K. I., Nakamura, A., & Fukuhara, K. (2014). Synthesis and radical-scavenging activity of a dimethyl catechin analogue. Bioorganic and Medicinal Chemistry Letters, 24(11), 2582-2584. https://doi.org/10.1016/j.bmcl.2014.03.029