Physicochemical properties of new S-derivatives of 5-(5-bromofuran-2-yl)-4-methyl-1,2,4-triazol-3-thiols

Abstract

The alkylation of 5-(5-bromofuran-2-yl)-4-methyl-1,2,4-triazole-3-thiol with bromoalkanes was carried out. Synthesis was accomplished by addition of equivalent amounts of bromoalkanes (bromomethane, bromoethane, bromobutane–bromodecane) to 5-(5-bromofuran-2-yl)-4-methyl-1,2,4-triazole-3-thiol in a methanol medium in the presence of an equivalent amount of sodium hydroxide. Compounds were obtained with a high yield. The next step was to investigate the reaction of 5-(5-bromofuran-2-yl)-4-methyl-1,2,4-triazole-3-thiol with some other halogen-containing compounds, the mechanism of the reaction of which also relates to nucleophilic substitution. As halogen-containing compounds, we used bromoacetone, bromoacetophenone, chloroacetic acid and chloroacetamide. Under these conditions, a series of new compounds were synthesized. Structure of compounds was confirmed by 1H NMR spectroscopy and elemental analysis. The antibacterial activity of the synthesized compounds towards cryogenic strains of Enterobacteriaceae, Pseudomonadaceae, Staphylococcaceae, Bacillaceae, Listeriaceae, Corynebacteriaceae and Saccharomycetaceae families in vitro was also investigated. According to the data obtained, one can conclude that the investigated compounds can compete with kanamycin, a natural broad-spectrum antibiotic from the second generation of aminoglycosides, whose range of action includes gram-positive and gram-negative microorganisms. The compounds involved may be recommended for further investigation of their action against multi-resistant strains of microorganisms.