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 CF3-substituted rhodanines) possess high log P 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.

New benciliden-rhodanines of the general structure A showed fungicidal properties against standardized and clinical fungi displaying potent activities against Candida, Cryptococcus and dermatophyte spp. SAR studies on the rhodanine compounds including the calculations of log P, dipole moments, and MEPs allowed to understand the minimal structural requirements for rhodanines to display antifungal activity.Figure optionsDownload as PowerPoint slide