Bioorganic & Medicinal Chemistry Letters 2010-04-01

Efficient microwave-assisted prenylation of pinostrobin and biological evaluation of its derivatives as antitumor agents.

Hadi Poerwono, Shigeru Sasaki, Yoshiyuki Hattori, Kimio Higashiyama

Index: Bioorg. Med. Chem. Lett. 20 , 2086-9, (2010)

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Abstract

Pinostrobin (5-hydroxy-7-methoxyflavanone) obtained in relatively large amounts from fingerroot (Boesenbergia pandurata) was converted to its C-6 and C-8 prenylated derivatives. The Mitsunobu reaction, europium(III)-catalyzed Claisen-Cope rearrangement, and Claisen reaction coupled with cross-metathesis were used as the key steps. Using a sealed-vessel microwave reactor, the Mitsunobu and Claisen/Cope reactions occurred smoothly with short reaction times and in satisfactory yields. The target compounds and five new intermediary substances showed cytotoxic activity toward SK-BR-3, MCF-7, PC-3, and Colo-320DM human tumor cell lines, and all of them had significantly lower IC(50) (microM) values than pinostrobin.Crown Copyright 2010. Published by Elsevier Ltd. All rights reserved.