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

4 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

Fingerprint

Catechin
Scavenging
Hydroxylation
Cyclization
Hydroxyl Radical
Antioxidants
Derivatives
Acids

Keywords

  • Antioxidant
  • Catechin
  • Radical scavenging
  • Synthetic antioxidant

ASJC Scopus subject areas

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

Cite this

Imai, K., Nakanishi, I., Ohno, A., Kurihara, M., Miyata, N., Matsumoto, K. I., ... 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

Synthesis and radical-scavenging activity of a dimethyl catechin analogue. / Imai, Kohei; Nakanishi, Ikuo; Ohno, Akiko; Kurihara, Masaaki; Miyata, Naoki; Matsumoto, Ken Ichiro; Nakamura, Asao; Fukuhara, Kiyoshi.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 24, No. 11, 01.06.2014, p. 2582-2584.

Research output: Contribution to journalArticle

Imai, K, Nakanishi, I, Ohno, A, Kurihara, M, Miyata, N, Matsumoto, KI, Nakamura, A & Fukuhara, K 2014, 'Synthesis and radical-scavenging activity of a dimethyl catechin analogue', Bioorganic and Medicinal Chemistry Letters, vol. 24, no. 11, pp. 2582-2584. https://doi.org/10.1016/j.bmcl.2014.03.029
Imai, Kohei ; Nakanishi, Ikuo ; Ohno, Akiko ; Kurihara, Masaaki ; Miyata, Naoki ; Matsumoto, Ken Ichiro ; Nakamura, Asao ; Fukuhara, Kiyoshi. / Synthesis and radical-scavenging activity of a dimethyl catechin analogue. In: Bioorganic and Medicinal Chemistry Letters. 2014 ; Vol. 24, No. 11. pp. 2582-2584.
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