Chemical and Pharmaceutical Bulletin p. 314 - 327 (1996)
Update date:2022-08-04
Topics: Synthesis Antifungal Optically active Azoles Antifungal Activity
Kitazaki, Tomoyuki
Tamura, Norikazu
Tasaka, Akihiro
Matsushita, Yoshihiro
Hayashi, Ryogo
Okonogi, Kenji
Itoh, Katsumi
A new series of optically active antifungal azoles, N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl) propyl]-N′-(4-substituted phenyl)-3(2H,4H)-1,2,4-triazolones (1,2) and 5(1H,4H)-tetrazolones (3), were prepared from the triflate derivative of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (13) by an SN2 displacement reaction with the union of an azolone (17-19) and subsequent ring-opening reaction with 1H-1,2,4-triazole. The optically active oxiranylethanol 13 was synthesized from methyl (R)-lactate in a stereocontrolled manner. The azolones 1-3 prepared showed potent antifungal activities in vitro and in vivo.
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