Synthesis and antifungal activity of (Z)-5-arylidenerhodanines

MAXIMILIANO SORTINO; PAULA DELGADO; SABINA JUAREZ; JAIRO QUIROGA; RODRIGO ABONIA; BRAULIO INSUASTY; MANUEL NOGUERAS; LAURA RODERO; FRANCISCO M. GARIBOTTO; RICARDO D. ENRIZ; SUSANA A. ZACCHINO

BIOORGANIC & MEDICINAL CHEMISTRY.

Elsevier Ltd

Lugar: San Diego, CA; Año: 2007 vol. 15 p. 484 - 494

0968-0896

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 CF3-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.