The synthesis and the antimicrobial activity of anionarylation products containing the sulfonamide fragment

Z. I. Yaniv, R. V. Symchak, O. V. Pokryshko, H. M. Tulaydan, V. S. Baranovskyy, S. I. Klymnyuk, B. D. Grishchuk

Abstract


Products containing the sulfonamide fragment have been synthesized by anionarylation reaction. 3-(4-Sulfonamidophenyl)2-thiocyanato(bromo)propanamides, 4-(2-thiocyanato(bromo, chloro)-2-phenylethyl)benzenesulfonamides, 2-(4-sulfonamidophenyl)fumaric and 2-bromo-3-(4-sulfonamidophenyl)butanedioic acids have been obtained by the copper-catalyst reaction of 4-sulfonamidophenyldiazonium tetrafluoroborate with acrylamide, styrene and fumaric acid with the yields of 36-82%. The anionarylation competing process is formation of 4-(iso)thiocyanato(chloro, bromo)benzenesulfonamides as Sandmeyer reaction products. In case of thiocyanatoarylation of fumaric acid 2-(4-sulfonamidophenyl)fumaric acid is selectively formed as an arylation product. The structure of the compounds synthesized has been confirmed by IR- and 1H NMR-spectra. The antimicrobial activity of these compounds in relation to the museum strains of staphylococcus, E.coli, aerobic bacillus and yeasts fungi has been studied. It has been found that sulfonamide derivatives are characterized by a high antibacterial and antifungal activity, which is the most pronounced for arylalkyl thiocyanates based on acrylamide. The research conducted has confirmed the positive impact of the sulfonamide fragment introduction in the structure of anionarylation products of unsaturated compounds to expand the range of the antimicrobial activity and decrease of the minimum inhibitory concentration.

Keywords


sulfonamides; 4-sulphonamidophenyldiazonium tetrafluoroborate; halogeno- and thiocyanatoarylation; antibacterial and antifungal properties

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DOI: https://doi.org/10.24959/ophcj.16.883

Abbreviated key title: Ž. org. farm. hìm.

ISSN 2518-1548 (Online), ISSN 2308-8303 (Print)