4-((5-(1-(4-Fluorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl)-1,3,4-thiadiazol-2-yl)amino)benzenesulfonic acid: unexpected synthesis, structure elucidation and antimicrobial activity

Abstract

Unexpected ring closure of 2-(1-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazole-4-carbonyl)-N-phenylhydrazine-1-carbothioamide (3) on exposure to sulfuric acid at room temperature for an extended duration (12 h) gave 4-((5-(1-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl)-1,3,4-thiadiazol-2-yl)amino)benzenesulfonic acid ( 4) in 75% yield. The use of sulfuric acid led to sulfonation at the para-pos-ition of the benzene ring in phenyl isothiocyanate. The crystal structure comprises two independent types of molecules of 4 and two disordered ether solvent molecules. The synthesized benzenesul-fonic acid inhibits the growth of both Listeria monocytogenes and Escherichia coli and its activity was comparable to those obtained for ampicillin and vancomycin.

In vitro and In silico Evaluation of Antibacterial Effects in Some Oxadiazole Compounds against Escherichia coli O157: H7

“…The presence of the fluorophenyl functional group in the synthesized structure may contribute to its antibacterial effect. In line with this, Kariuki et al synthesized fluorophenyl structures and demonstrated that these compounds inhibited the growth of both Listeria monocytogenes and E. coli, with activity levels comparable to those of ampicillin and vancomycin (29).…”