Optically Active Antifungal Azoles. VI. Synthesis and Antifungal Activity of 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 and 5(1H, 4H)-tetrazolones

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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 anion 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 stereo-controlled manner. The azolones 1-3 prepared showed potent antifungal activities in vitro and in vivo.
公益社団法人日本薬学会の論文
1996-02-15