Synthesis and antifungal activity of (Z)-5-arylidenerhodanines.
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.
Sortino
Maximiliano
M
Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, (2000), Rosario, Argentina.
Delgado
Paula
P
Juárez
Sabina
S
Quiroga
Jairo
J
Abonía
Rodrigo
R
Insuasty
Braulio
B
Nogueras
Manuel
M
Rodero
Laura
L
Garibotto
Francisco M
FM
Enriz
Ricardo D
RD
Zacchino
Susana A
SA
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*
D000935:Antifungal Agents; D012236:Rhodanine