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. (2nd January 2023)

• Record Type: Journal Article
• Authors: Kariuki, Benson M.; Mohamed, Hanan A.; Abdel-Wahab, Bakr F.; El-Hiti, Gamal A.
• Is Part Of: Phosphorus, sulfur, and silicon and the related elements. Volume 198:Number 1(2023)
• Page Start: 10
• Page End: 14
• Publication Date: 2023-01-02
• Subjects: 4-(1, 3, 4-Thiadiazol-2-yl)amino)benzenesulfonic acid -- phenyl isothiocyanate -- 1, 2, 3-triazole -- antimicrobial activity -- X-ray crystallography; Sulfur compounds -- Periodicals; Organosulfur compounds -- Periodicals; Phosphorus compounds -- Periodicals; Organophosphorus compounds -- Periodicals; Silicon compounds -- Periodicals; Organosilicon compounds -- Periodicals; 546
• DOI: 10.1080/10426507.2022.2099858
• Languages: English
• ISSNs: 1042-6507

Abstract

Abstract: Unexpected ring closure of 2-(1-(4-fluorophenyl)-5-methyl-1 H -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-1 H -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 -position 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 benzenesulfonic acid inhibits the growth of both Listeria monocytogenes and Escherichia coli and its activity was comparable to those obtained for ampicillin and vancomycin. Graphical Abstract: UF0001