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Synthesis and biological activity of desmethoxy analogues of coruscanone A
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SYSNO ASEP 0367571 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Synthesis and biological activity of desmethoxy analogues of coruscanone A Author(s) Tichotová, L. (CZ)
Matoušová, E. (CZ)
Špulák, M. (CZ)
Kuneš, J. (CZ)
Votruba, Ivan (UOCHB-X) RID
Buchta, V. (CZ)
Pour, M. (CZ)Number of authors 7 Source Title Bioorganic and Medicinal Chemistry Letters. - : Elsevier - ISSN 0960-894X
Roč. 21, č. 20 (2011), s. 6062-6066Number of pages 5 s. Language eng - English Country GB - United Kingdom Keywords cyclopentenediones ; knoevenagel ; Lewis acid ; antifungal ; cytotoxicity Subject RIV CC - Organic Chemistry R&D Projects 1M0508 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000295494500007 DOI 10.1016/j.bmcl.2011.08.059 Annotation 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. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2012
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