Antifungal estrogen-like imidazoles. Synthesis and antifungal activities of thienyl and 1H-pyrrolyl derivatives of 1-aryl-2-(1H-imidazol-1-yl)ethane

Article abstract of DOI:10.1016/S0223-5234(97)87541-1

Reaction of arylacetyl chlorides on thiophene or pyrrole derivatives furnished 2-aryl-1-(2-thienyl)- or 2-aryl-1-(1H-pyrrol-2-yl)-1-ethanones. Reduction of ketones to the corresponding carbinols and reaction of the latter compounds with 1,1'-sulfonyldiimidazole or 1,1'-carbonyldiimidazole gave 2-thienyl- and 1H-pyrrol-2-yl-1-aryl-2-(1H-imidazol-1-yl)ethanes, respectively. The new compounds were tested in vitro against a variety of pathogenic fungi in comparison with miconazole and bifonazole. Some a 5-chloro-2-thienyl derivatives were endowed with good antifungal activity, particularly against Candida albicans and Cryptococcus neoformans.