title: Synthesis and radical-scavenging activity of a dimethyl catechin analogue.
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.
authors.affiliation: Department of Applied Chemistry, Shibaura Institute of Technology, Fukasaku, Minuma-ku, Saitama 337-8570, Japan.
authors.forename: Kohei
authors.initials: K
authors.lastname: Imai
authors.affiliation: Research Center for Charged Particle Therapy, National Institute of Radiological Sciences, Inage-ku, Chiba 263-8555, Japan.
authors.forename: Ikuo
authors.initials: I
authors.lastname: Nakanishi
authors.affiliation: Division of Organic Chemistry, National Institute of Health Sciences, Setagaya-ku, Tokyo 158-8501, Japan.
authors.forename: Akiko
authors.initials: A
authors.lastname: Ohno
authors.affiliation: Division of Organic Chemistry, National Institute of Health Sciences, Setagaya-ku, Tokyo 158-8501, Japan.
authors.forename: Masaaki
authors.initials: M
authors.lastname: Kurihara
authors.affiliation: Graduate School of Pharmaceutical Sciences, Nagoya City University, Mizuho-ku, Nagoya, Aichi 467-8603, Japan.
authors.forename: Naoki
authors.initials: N
authors.lastname: Miyata
authors.affiliation: Research Center for Charged Particle Therapy, National Institute of Radiological Sciences, Inage-ku, Chiba 263-8555, Japan.
authors.forename: Ken-Ichiro
authors.initials: K
authors.lastname: Matsumoto
authors.affiliation: Department of Applied Chemistry, Shibaura Institute of Technology, Fukasaku, Minuma-ku, Saitama 337-8570, Japan.
authors.forename: Asao
authors.initials: A
authors.lastname: Nakamura
authors.affiliation: School of Pharmacy, Showa University, Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan. Electronic address: fukuhara@pharm.showa-u.ac.jp.
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Fukuhara
mesh_terms: D002392:Catechin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D003500:Cyclization; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008968:Molecular Conformation
chemical_list: C000593992:2-(3,4-dihydroxy-2,5-dimethylphenyl)chroman-3,5,7-triol; D016166:Free Radical Scavengers; D002392:Catechin
keywords: Antioxidant; Catechin; Radical scavenging; Synthetic antioxidant