title: Synthesis and biological activity of desmethoxy analogues of coruscanone A.
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.
authors: 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.
authors: Lucie
authors: L
authors: Tichotová
authors: Eliška
authors: E
authors: Matoušová
authors: Marcel
authors: M
authors: Spulák
authors: Jiří
authors: J
authors: Kuneš
authors: Ivan
authors: I
authors: Votruba
authors: Vladimír
authors: V
authors: Buchta
authors: Milan
authors: M
authors: Pour
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002175:Candida / Q000187:drug effects*; D002177:Candidiasis / Q000188:drug therapy; D002460:Cell Line; D045744:Cell Line, Tumor; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D051379:Mice; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship
chemical_list: D000935:Antifungal Agents; D003517:Cyclopentanes; C569339:coruscanone A; C004511:butenolide; D015107:4-Butyrolactone