title: Antimycotic imidazoles. 2. Synthesis and antifungal properties of esters of 1-[2-hydroxy(mercapto)-2-phenylethyl]-1H-imidazoles.
abstract: The synthesis of carboxylic and (thio)carbonate esters of 1-[2-hydroxy(mercapto)-2-phenylethyl]-1-H-imidazoles, some of which are formally related to miconazole and its analogues by replacement of an ether with an ester linkage, is described. In antifungal bioassays a number of compounds display in vitro and, in a few cases, in vivo activities comparable to that of miconazole. In this series lipophilicity within a relatively narrow range is shown to be a necessary, although not sufficient, criterion for in vitro and, in particular, in vivo antifungal activity.
mesh_terms: D000818:Animals; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000627:therapeutic use; D002177:Candidiasis / Q000188:drug therapy; D004952:Esters / Q000138:chemical synthesis / Q000494:pharmacology; D005260:Female; D007093:Imidazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D051379:Mice; D008826:Microbial Sensitivity Tests; D012995:Solubility; D013329:Structure-Activity Relationship
chemical_list: D000935:Antifungal Agents; D004952:Esters; D007093:Imidazoles