[Enantioselective synthesis and antifungal activity of optically active econazole and miconazole].
In an effort to investigate the relationship between stereochemistry 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.
Liao
Y W
YW
Department of Chemistry, Second Military Medical University, Shanghai.
Li
H X
HX
D002176:Candida albicans / Q000187:drug effects; D004464:Econazole / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008825:Miconazole / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008864:Microsporum / Q000187:drug effects; D013237:Stereoisomerism; D014249:Trichophyton / Q000187:drug effects
D004464:Econazole; D008825:Miconazole