Bioorganic & Medicinal Chemistry Letters 2011-10-15

Synthesis and biological activity of desmethoxy analogues of coruscanone A.

Lucie Tichotová, Eliška Matoušová, Marcel Spulák, Jiří Kuneš, Ivan Votruba, Vladimír Buchta, Milan Pour

Index: Bioorg. Med. Chem. Lett. 21(20) , 6062-6, (2011)

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Abstract

A series of simple desmethoxy analogues of coruscanone A was prepared via a novel version of Ti(iPrO)(4)-mediated Knoevenagel condensation of cyclopentenedione with substituted benzaldehydes and cinnamic aldehydes, and the compounds were evaluated for antifungal activity and cytotoxicity. The most potent 2-benzylidenecyclopent-4-ene-1,3-dione possessed antifungal effect comparable to coruscanone A and a somewhat broader spectrum of activity against Candida species. The compound was also superior to fluconazole against several non-albicans Candida sp. Evaluation of the ability of the compound to influence cell proliferation using two different assays showed that 2-benzylidenecyclopent-4-ene-1,3-dione has lower cytotoxicity compared to the natural product.Copyright © 2011 Elsevier Ltd. All rights reserved.