Synthesis and biological activity of desmethoxy analogues of coruscanone A |
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Authors: | Tichotová Lucie Matou?ová Eli?ka Spulák Marcel Kune? Ji?í Votruba Ivan Buchta Vladimír Pour Milan |
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Institution: | Centre for New Antivirals and Antineoplastics, Department of Inorganic and Organic Chemistry, Charles University, Faculty of Pharmacy, Heyrovského 1203, CZ-500 03 Hradec Králové, Czech Republic. |
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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. |
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Keywords: | Cyclopentenediones Knoevenagel Lewis acid Antifungal Cytotoxicity |
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