Synthesis and enhanced radical scavenging activity of a conformationally constrained epigallocatechin analogue

Kohei Imai; Ikuo Nakanishi; Kazunori Anzai; Toshihiko Ozawa; Naoki Miyata; Shiro Urano; Haruhiro Okuda; Asao Nakamura; Kiyoshi Fukuhara

doi:10.1246/cl.2011.1417

Synthesis and enhanced radical scavenging activity of a conformationally constrained epigallocatechin analogue

Kohei Imai, Ikuo Nakanishi, Kazunori Anzai, Toshihiko Ozawa, Naoki Miyata, Shiro Urano, Haruhiro Okuda, Asao Nakamura, Kiyoshi Fukuhara

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

The freely rotating single bond between the pyrogallol and chroman substructures in epigallocatechin (EGC) was constrained by reaction of EGC with acetone in the presence of trimethylsilyl trifluoromethanesulfonate to prepare the rigidified analog in good yield. The synthesized analog was examined for free radical scavenging activity toward the galvinoxyl radical and was found to be 27-fold more potent than EGC.

Original language	English
Pages (from-to)	1417-1419
Number of pages	3
Journal	Chemistry Letters
Volume	40
Issue number	12
DOIs	https://doi.org/10.1246/cl.2011.1417
Publication status	Published - 2011

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.2011.1417

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title = "Synthesis and enhanced radical scavenging activity of a conformationally constrained epigallocatechin analogue",

abstract = "The freely rotating single bond between the pyrogallol and chroman substructures in epigallocatechin (EGC) was constrained by reaction of EGC with acetone in the presence of trimethylsilyl trifluoromethanesulfonate to prepare the rigidified analog in good yield. The synthesized analog was examined for free radical scavenging activity toward the galvinoxyl radical and was found to be 27-fold more potent than EGC.",

author = "Kohei Imai and Ikuo Nakanishi and Kazunori Anzai and Toshihiko Ozawa and Naoki Miyata and Shiro Urano and Haruhiro Okuda and Asao Nakamura and Kiyoshi Fukuhara",

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T1 - Synthesis and enhanced radical scavenging activity of a conformationally constrained epigallocatechin analogue

AU - Imai, Kohei

AU - Nakanishi, Ikuo

AU - Anzai, Kazunori

AU - Ozawa, Toshihiko

AU - Miyata, Naoki

AU - Urano, Shiro

AU - Okuda, Haruhiro

AU - Nakamura, Asao

AU - Fukuhara, Kiyoshi

PY - 2011

Y1 - 2011

N2 - The freely rotating single bond between the pyrogallol and chroman substructures in epigallocatechin (EGC) was constrained by reaction of EGC with acetone in the presence of trimethylsilyl trifluoromethanesulfonate to prepare the rigidified analog in good yield. The synthesized analog was examined for free radical scavenging activity toward the galvinoxyl radical and was found to be 27-fold more potent than EGC.

AB - The freely rotating single bond between the pyrogallol and chroman substructures in epigallocatechin (EGC) was constrained by reaction of EGC with acetone in the presence of trimethylsilyl trifluoromethanesulfonate to prepare the rigidified analog in good yield. The synthesized analog was examined for free radical scavenging activity toward the galvinoxyl radical and was found to be 27-fold more potent than EGC.

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JO - Chemistry Letters

JF - Chemistry Letters

SN - 0366-7022

IS - 12

ER -

Synthesis and enhanced radical scavenging activity of a conformationally constrained epigallocatechin analogue

Abstract

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