ENANTIOSELECTIVE SYNTHESIS AND ANTIFUNGAL ACTIVITY OF OPTICALLY ACTIVE ECONAZOLE AND MICONAZOLE

In an effort to investigate the relationship between stereochernistry and antifungal activity of the antimycotic agents, optically active econazole and miconazole were first enantioselectively synthesized. The key step was the enantioselective reduction of 2-chloro-1-(2,4-dichlorophenyl) ethanone catalyzed by chiral oxazaborolidine.Preliminary biological tests showed that (R)- (-)- econazole and ( R)- (-)- miconazole were more active than the (S)-isomer and racemates against common pathogenic fungi such as Candida albicans, Trichophyton rubrum, T. gypseum, Microsporum lanosum and Aspergillus flavus in vitro.