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

Kariuki, Benson M. ORCID: https://orcid.org/0000-0002-8658-3897, Mohamed, Hanan A., Abdel-Wahab, Bakr F. and El-Hiti, Gamal A. 2023. 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. Phosphorus, Sulfur, and Silicon and the Related Elements 198 (1) , pp. 10-14. 10.1080/10426507.2022.2099858

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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-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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	Taylor and Francis Group
ISSN:	1042-6507
Funders:	King Saud University, Riyadh, Saudi Arabia
Date of First Compliant Deposit:	30 August 2022
Date of Acceptance:	6 July 2022
Last Modified:	25 Nov 2024 07:15
URI:	https://orca.cardiff.ac.uk/id/eprint/152224

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