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

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5 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 languageEnglish
Pages (from-to)1417-1419
Number of pages3
JournalChemistry Letters
Volume40
Issue number12
DOIs
Publication statusPublished - 2011 Dec 1

ASJC Scopus subject areas

  • Chemistry(all)

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    Imai, K., Nakanishi, I., Anzai, K., Ozawa, T., Miyata, N., Urano, S., Okuda, H., Nakamura, A., & Fukuhara, K. (2011). Synthesis and enhanced radical scavenging activity of a conformationally constrained epigallocatechin analogue. Chemistry Letters, 40(12), 1417-1419. https://doi.org/10.1246/cl.2011.1417