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

doi:10.1016/j.bmcl.2014.03.029

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 journal › Article › peer-review

9 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 language	English
Pages (from-to)	2582-2584
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	24
Issue number	11
DOIs	https://doi.org/10.1016/j.bmcl.2014.03.029
Publication status	Published - 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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10.1016/j.bmcl.2014.03.029

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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.",

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T1 - Synthesis and radical-scavenging activity of a dimethyl catechin analogue

AU - Imai, Kohei

AU - Nakanishi, Ikuo

AU - Ohno, Akiko

AU - Kurihara, Masaaki

AU - Miyata, Naoki

AU - Matsumoto, Ken Ichiro

AU - Nakamura, Asao

AU - Fukuhara, Kiyoshi

PY - 2014/6/1

Y1 - 2014/6/1

N2 - 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.

AB - 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.

KW - Antioxidant

KW - Catechin

KW - Radical scavenging

KW - Synthetic antioxidant

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Synthesis and radical-scavenging activity of a dimethyl catechin analogue

Abstract

Keywords

ASJC Scopus subject areas

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