Optically Active Antifungal Azoles. III. Synthesis and Antifungal Activity of Sulfide and Sulfonamide Derivatives of (2R, 3R)-2-(2, 4-Difluorophenyl)-3-mercapto-1-(1H, 1, 2, 4-triazol-1-yl)-2-butanol

Akihiro TASAKA; Katsunori TERANISHI; Yoshihiro MATSUSHITA; Norikazu TAMURA; Ryogo HAYASHI; Kenji OKONOGI; Katsumi ITOH

doi:10.1248/cpb.42.85

Akihiro TASAKA, Katsunori TERANISHI, Yoshihiro MATSUSHITA, Norikazu TAMURA, Ryogo HAYASHI, Kenji OKONOGI, Katsumi ITOH

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Keywords: optically active antifungal azole, sulfide, sulfonamide, triazolylbutanol, antifungal activity, candidosis

JOURNAL FREE ACCESS

1994 Volume 42 Issue 1 Pages 85-94

DOI https://doi.org/10.1248/cpb.42.85

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Abstract

In an effort to find potent antifungal agents, optically active sulfur-containing triazole derivatives, sulfides (3) and sulfonamides (4), were prepared and evaluated for antifungal activity against Candida albicans in vitro and in vivo. The sulfides (3) were prepared by the reaction of (2R, 3R)-2-(2, 4-difluorophenyl)-3-mercapto-1-(1H, 1, 2, 4-triazol-1-yl)-2-butanol (1) with various heteroarylmethyl chlorides in the presence of sodium methoxide. The sulfonamides (4) were synthesized starting from the disulfide (15) in three steps including oxidation of the corresponding sulfenamides (17). Some of the sulfur-containing triazole derivatives (3, 4) showed strong protective effects against candidosis in mice.

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