Antifungal properties of substituted 1-phenyl-5-mercaptotetrazoles and their oxidation product, 5-bis-(1-phenyltetrazolyl)disulfide

Abstract

The antifungal effect of substituted 1-phenyl-5-mercaptotetrazoles was tested withCandida tropicalis, C. pseudotropicalis, C. mogii, Trichosporon cutaneum, Cryptococcus albidus andS. cerevisiae. Candida strains exhibited the lowest sensitivity to the compounds; the most sensitive wasS. 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 onE1/2 andI₁. 5-Bis-(1-phenyltetrazolyl)disulfide, the compound with no antifungal effect, has been identified as the main oxidation product of 1-phenyl-5-mercaptotetrazole.