title: 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-b utanol.
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.
authors.affiliation: Pharmaceutical Research Laboratory III, Pharmaceutical Research Division, Takeda Chemical Industries Ltd., Osaka, Japan.
authors.forename: A
authors.initials: A
authors.lastname: Tasaka
authors.forename: K
authors.initials: K
authors.lastname: Teranishi
authors.forename: Y
authors.initials: Y
authors.lastname: Matsushita
authors.forename: N
authors.initials: N
authors.lastname: Tamura
authors.forename: R
authors.initials: R
authors.lastname: Hayashi
authors.forename: K
authors.initials: K
authors.lastname: Okonogi
authors.forename: K
authors.initials: K
authors.lastname: Itoh
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D013440:Sulfides / Q000138:chemical synthesis* / Q000494:pharmacology; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000494:pharmacology; D014230:Triazoles / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000935:Antifungal Agents; D013440:Sulfides; D013449:Sulfonamides; D014230:Triazoles