Synthesis and Structural Characterization of Some Potential Anti-Virulence 1,2,4-Triazoles and 1,3,4-Thiadiazoles

This paper presents a continuation of our studies in the synthesis of some 1,2,4-triazole-3-thiones and 1,3,4-thiadiazol-2-amines containing in their molecules the fluorine atom. For the synthesis of these heterocycles, the hydrazinecarbothioamides, 2-(4-(4-X-phenylsulfonyl)benzoyl)-N-(3-fluorophenyl) hydrazinecarbo-thioamides 2a-c, were obtained by treatment of some 4-(4-X-phenylsulfonyl)-benzoic acid hydrazides 1a-c with 3-fluorophenyl isothiocyanate. The new 5-(4-(4-X-phenylsulfonyl)phenyl)-4-(3-fluorophenyl)-2H-1,2,4-triazole-3(4H)-thiones 3a-c were obtained by refluxing of hydrazinecarbothioamide 2a-c with a solution natrium hidroxide and the 5-(4-(4-X-phenylsulfonyl)phenyl)-N-(3-fluorophenyl)-1,3,4-thiadiazol-2-amines 4a-c were synthesized by refluxing of hydrazinecarbothioamides 2a-c with phosphorus oxychloride. The newly synthesized compounds were characterized by IR, 1H-NMR, 13C-NMR, mass spectral data and by elemental analysis. The compounds have been tested on Daphnia magna for their toxicity assessment.