Antibacterial and antifungal agents. XV. Synthesis and antifungal activity of structural analogues of bifonazole and ketoconazole.

ABSTRACT

The synthesis and antifungal activities of the cis- and trans-1-acetyl-4-[4-[[2-(1,1'-biphenyl-4-yl)-2-(1H-imidazol-1-ylmethy l)- 1,3-dioxolan-4-yl]-methoxy]phenyl)piperazines 3 and 4 are reported. Stereochemical assignments to diastereomeric pairs of cis/trans isomers were made on the basis of 1H- and 13C-NMR data. Among test derivatives the best activity was shown by the benzoyl esters of the cis- and trans-[2-(1,1'-biphenyl-4-yl)-2-(1H-imidazol-1-ylmethyl)-1,3-di oxolan-4- yl]methanols 9 and 10.