title: 3,5-disubstituted pyranone analogues of highly antifungally active furanones: conversion of biological effect from antifungal to cytostatic.
abstract: A series of 3-aryl-5-acyloxymethyl-5,6-dihydro-2H-pyran-2-ones, related to highly antifungally active butenolides, was synthesized via cyclization of substituted δ-hydroxy acids as the key step, and evaluated for their in vitro antifungal activity and cytostatic activity. While the extension of the furanone ring to pyranone led to a complete loss of the antifungal effect, some of the compounds displayed promising effect against several cell lines, including the resistant colorectal carcinoma cells.
authors.affiliation: Centre for New Antivirals and Antineoplastics, Department of Inorganic and Organic Chemistry, Charles University in Prague, Faculty of Pharmacy in Hradec Králové, Hradec Králové, Czech Republic.
authors.forename: Radan
authors.initials: R
authors.lastname: Schiller
authors.forename: Lucie
authors.initials: L
authors.lastname: Tichotová
authors.forename: Jan
authors.initials: J
authors.lastname: Pavlík
authors.forename: Vladimír
authors.initials: V
authors.lastname: Buchta
authors.forename: Bohuslav
authors.initials: B
authors.lastname: Melichar
authors.forename: Ivan
authors.initials: I
authors.lastname: Votruba
authors.forename: Jirí
authors.initials: J
authors.lastname: Kunes
authors.forename: Marcel
authors.initials: M
authors.lastname: Spulák
authors.forename: Milan
authors.initials: M
authors.lastname: Pour
mesh_terms: D000818:Animals; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D045744:Cell Line, Tumor; D054697:Cytostatic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D051379:Mice; D011714:Pyrans / Q000737:chemistry*
chemical_list: D000935:Antifungal Agents; D054697:Cytostatic Agents; D005663:Furans; D011714:Pyrans