Antifungal properties of substituted 1-phenyl-5-mercaptotetrazoles and their oxidation product, 5-bis-(1-phenyltetrazolyl)disulfide.
The antifungal effect of substituted 1-phenyl-5-mercaptotetrazoles was tested with Candida tropicalis, C. pseudotropicalis, C. mogii, Trichosporon cutaneum, Cryptococcus albidus and S. cerevisiae. Candida strains exhibited the lowest sensitivity to the compounds; the most sensitive was S. cerevisiae. The MIC values ranged from 40 to > 1000 mg/mL. The antifungal effect of halogenated compounds decreased in the series of bromo > chloro > fluoro derivatives. The electrochemical oxidation of substituted 1-phenyl-5-mercaptotetrazole derivatives in an acetonitrile medium was studied as a model for the enzymic oxidation of the substance, including study of the effect of water, perchloric and trifluoromethanesulfuric acids on E1/2 and I1. 5-Bis-(1-phenyltetrazolyl)disulfide, the compound with no antifungal effect, has been identified as the main oxidation product of 1-phenyl-5-mercaptotetrazole.
Nesmĕrák
K
K
Department of Analytical Chemistry, Faculty of Science, Charles University, 128 43 Prague, Czechia.
Pospísek
M
M
Nĕmec
I
I
Waisser
K
K
Gabriel
J
J
D000097:Acetonitriles / Q000378:metabolism; D000935:Antifungal Agents / Q000494:pharmacology*; D002851:Chromatography, High Pressure Liquid; D004220:Disulfides / Q000494:pharmacology*; D004572:Electrolysis; D005658:Fungi / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D013777:Tetrazoles / Q000494:pharmacology*
D000097:Acetonitriles; D000935:Antifungal Agents; D004220:Disulfides; D013777:Tetrazoles; C025766:1-phenyl-5-mercaptotetrazole; C032159:acetonitrile