The Synthesis of trans-Flavan-3-ol Gallates by Regioselective Oxidative Etherification and Their Cytotoxicity Mediated by 67 LR

Nana Shiraishi, Motofumi Kumazoe, Shinichiro Fuse, Hirofumi Tachibana, Hiroshi Tanaka

研究成果: Contribution to journalArticle査読

4 被引用数 (Scopus)

抄録

We report on a chiral pool approach for the synthesis of trans-flavan-3-ol gallates from epichlorohydrin. The trans-flavan-3-ol gallates were prepared by the cycloetherification of the phenol at the C2 benzylic position of 2-acylozyl-1,3-diarylpropane during regioselective C−H oxidation. The 1,3-diarylpropanes were prepared starting from epichlorohydrin by epoxide opening with A and B ring precursors, followed by acylation of the resultant alcohol with galloyl chloride. The availability of both the enantiomers of epichlorohydrin allowed the preparation of the corresponding enantiomer using the same procedure. The cytotoxicity of the compounds against U266 cells was tested, in which 5-deoxy-7,3′-O-dimethyl gallocatechin gallate exhibited cytotoxicity that was more than ten times stronger than natural (−)-EGCG. In addition, the absolute configuration of the derivatives did not critically affect the biological activity.

本文言語英語
ページ(範囲)13050-13053
ページ数4
ジャーナルChemistry - A European Journal
22
37
DOI
出版ステータス出版済み - 9 5 2016

All Science Journal Classification (ASJC) codes

  • 触媒
  • 有機化学

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