Design,synthesis,and molecular docking of 1-(1-(4-chlorophenyl)-2-(phenylsulfonyl)ethylidene)-2-phenylhydrazine as potent nonazole anticandidal agent

1-(1-(4-chlorophenyl)-2-(phenylsulfonyl)ethylidene)-2-phenylhydrazine (13) was designed and synthesized as potential nonazole anticandidal agent and precisely characterized by ir,1h nmr,13c nmr,and esi-ms. the anti-candida activity of 13 was evaluated against four candida species (c. albicans,c. krusei,c. parapsilosis,and c. glabrata). compound 13 displayed good anticandidal activities (mic=0.39,0.195,0.39,and 1.56 μmol/ml,resp.) in comparison with that of the standard drug fluconazole (mic=0.195,inactive,1.56,and 1.56 μmol/ml,resp.) against c. albicans,c. krusei,c. parapsilosis,and c. glabrata,respectively. a molecular modeling of the newly synthesized compound 13 was built in order to investigate its mode of action towards the prospective target cytochrome p450-dependent enzyme lanosterol 14α-demethylase (pdb-code: 1ea1). the docking results showed a similar binding interaction of 13 and fluconazole at the active site of cyt p450 14α-sterol demethylase. furthermore,compound 13 showed no cytotoxicity against normal human breast cell line mcf10a. © 2014 hazem a. ghabbour et al.