Synthesis and biological activity of desmethoxy analogues of coruscanone A

0367571 - ÚOCHB 2012 RIV GB eng J - Journal Article
Tichotová, L. - Matoušová, E. - Špulák, M. - Kuneš, J. - Votruba, Ivan - Buchta, V. - Pour, M.
Synthesis and biological activity of desmethoxy analogues of coruscanone A.
Bioorganic and Medicinal Chemistry Letters. Roč. 21, č. 20 (2011), s. 6062-6066. ISSN 0960-894X. E-ISSN 1464-3405
R&D Projects: GA MŠMT 1M0508
Grant - others:GA ČR(CZ) GAP207/10/2048
Institutional research plan: CEZ:AV0Z40550506
Keywords : cyclopentenediones * knoevenagel * Lewis acid * antifungal * cytotoxicity
Subject RIV: CC - Organic Chemistry
Impact factor: 2.554, year: 2011

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.
Permanent Link: http://hdl.handle.net/11104/0202201