title: Synthesis and antifungal activity of (Z)-5-arylidenerhodanines.
abstract: An efficient microwave-assisted synthesis of new (Z)-5-arylidenerhodanines under solvent-free conditions is described and their in vitro antifungal activity was evaluated following the CLSI (formerly NCCLS) guidelines against a panel of both standardized and clinical opportunistic pathogenic fungi. An analysis of the structure-activity relationship (SAR) along with computational studies showed that the most active compounds (F- and CF(3)-substituted rhodanines) possess high logP values and low polarizability. Mechanism-based assays suggest that active compounds neither would bind to ergosterol nor would produce a damage to the fungal membrane.
authors.affiliation: Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, (2000), Rosario, Argentina.
authors.forename: Maximiliano
authors.initials: M
authors.lastname: Sortino
authors.forename: Paula
authors.initials: P
authors.lastname: Delgado
authors.forename: Sabina
authors.initials: S
authors.lastname: Juárez
authors.forename: Jairo
authors.initials: J
authors.lastname: Quiroga
authors.forename: Rodrigo
authors.initials: R
authors.lastname: Abonía
authors.forename: Braulio
authors.initials: B
authors.lastname: Insuasty
authors.forename: Manuel
authors.initials: M
authors.lastname: Nogueras
authors.forename: Laura
authors.initials: L
authors.lastname: Rodero
authors.forename: Francisco M
authors.initials: FM
authors.lastname: Garibotto
authors.forename: Ricardo D
authors.initials: RD
authors.lastname: Enriz
authors.forename: Susana A
authors.initials: SA
authors.lastname: Zacchino
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000528:radiation effects; D003198:Computer Simulation; D015195:Drug Design; D008826:Microbial Sensitivity Tests; D008872:Microwaves; D003904:Mitosporic Fungi / Q000187:drug effects*; D015394:Molecular Structure; D012236:Rhodanine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology; D012680:Sensitivity and Specificity; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D015003:Yeasts / Q000187:drug effects*
chemical_list: D000935:Antifungal Agents; D012236:Rhodanine