Differential antifungal effects of stereoisomeric styrylimidazole compounds on Candida albicans and Trichophyton rubrum.

New active antifungalagents with 1-(2-phenyl-1-alkenyl)-1H-imidazole structure were prepared and their structure-activity relationships were examined.The most potential activity among these derivatives was observed in Z-2-(2,4-dichlorophenyl)-3-methyl-1-pentenyl-1H-imidazole (coded as GBR-14206), which displayed a marked activity against not only Candida but Trichophyton.It was of particular interest to note that the antifungal profiles of these styrylimidazole derivatives were dependent on the geometry in the styryl portion; the Z-isomers were found to be more potent against Candida than the corresponding E-isomers, whereas the E-isomers were more effective for Trichophyton.Thus, the geometry in the styryl portion of 1-(2-phenyl-1-alkenyl)-1H-imidazole derivatives is crucial for their differential antifungal potency.