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

Authors

  • Z. I. Yaniv Ternopil national pedagogical university, Ukraine
  • R. V. Symchak Ternopil national pedagogical university, Ukraine
  • O. V. Pokryshko Ternopil State Medical University, Ukraine
  • H. M. Tulaydan Ternopil national pedagogical university, Ukraine
  • V. S. Baranovskyy Ternopil national pedagogical university, Ukraine
  • S. I. Klymnyuk Ternopil State Medical University, Ukraine
  • B. D. Grishchuk Ternopil national pedagogical university, Ukraine

DOI:

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

Keywords:

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

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.

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Published

2016-06-21

How to Cite

(1)
Yaniv, Z. I.; Symchak, R. V.; Pokryshko, O. V.; Tulaydan, H. M.; Baranovskyy, V. S.; Klymnyuk, S. I.; Grishchuk, B. D. The Synthesis and the Antimicrobial Activity of Anionarylation Products Containing the Sulfonamide Fragment. J. Org. Pharm. Chem. 2016, 14, 60-64.

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Section

Original Researches