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

研究成果: Article › 査読

9 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	2582-2584
ページ数	3
ジャーナル	Bioorganic and Medicinal Chemistry Letters
巻	24
号	11
DOI	https://doi.org/10.1016/j.bmcl.2014.03.029
出版ステータス	Published - 2014 6月 1

ASJC Scopus subject areas

生化学
分子医療
分子生物学
薬科学
創薬
臨床生化学
有機化学

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10.1016/j.bmcl.2014.03.029

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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

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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

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