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

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.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Poerwono H,Sasaki S,Hattori Y,Higashiyama K

doi

10.1016/j.bmcl.2010.02.068

subject

Has Abstract

pub_date

2010-04-01 00:00:00

pages

2086-9

issue

7

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(10)00268-4

journal_volume

20

pub_type

杂志文章

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