Antimicrobial activity of n-heterocyclic compounds containing coumarin moiety

  • O. V. Skrypska Yuriy Fedkovych Chernivtsi National University
  • O. V. Blinder L. I. Medved's Research Center of Preventive Toxicology, Food and Chemical Safety, Department of Medical and Ecological Problems, Chernivtsi
  • О. V. Yelenich Yuriy Fedkovych Chernivtsi National University
  • R. Z. Lytvyn Ivan Franko National University of Lviv
  • A. O. Neshchadin Ivan Franko National University of Lviv
  • M. D. Obushak Ivan Franko National University of Lviv
  • P. I. Yagodinets Yuriy Fedkovych Chernivtsi National University
Keywords: synthesis, antimicrobial activity, coumarin, quaternary salts, nitrogencontaining heterocycles, arylation

Abstract

Coumarin derivatives with different heterocyclic systems in the position 3 exhibit antibacterial activity. The aim of the work was the synthesis of new coumarin containing heterocyclic ensembles , the study of physical and chemical properties and biological activity of these compounds. As the starting reagent 3-(4-acetylphenyl)-2H-2-chromenone (I) was used. This compound by the reaction of coumarin with 4-acetyl benzenediazonium chloride was synthesized. By bromination of compound (I) 3-[4-(2-bromoacetyl)phenyl]-2H-2-chromenone (II) was obtained. By the reactions of compound (II) with pyridine, 4-methylpyridine, quinoline, benzo[f]quinoline and triphenylphosphine a quaternary salts was prepared. Compound (II) reacts with binucleophilic reagents to form thiazole, imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine and imidazo[2,1-i]purine derivatives. On the base of experimental microbiological studies we have established that compound (II), 3-(4-imidazo[1,2-a]pyrimidin-2-ylphenyl)-2H-2-chromenone (XIII) and 3-[4-(1H-imidazo[2,1-i]purin-8-yl)phenyl]-2H-2-chromenone (XIV) exhibit antimicrobial activity against strain S. aureus ATCC 25923 at low concentrations. Compounds (II, XIV) and 4-(2-oxo-2-[4-(2-oxo-2H-3-chromenyl)phenyl]ethyl)benzo[f]quinolinium bromide (VI) exhibit antimicrobial activity against strain B. subtilis ATCC 6633.

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Published
2019-02-12
How to Cite
Skrypska, O. V., Blinder, O. V., YelenichО. V., Lytvyn, R. Z., Neshchadin, A. O., Obushak, M. D., & Yagodinets, P. I. (2019). Antimicrobial activity of n-heterocyclic compounds containing coumarin moiety. Farmatsevtychnyi Zhurnal, (6), 69-77. Retrieved from https://pharmj.org.ua/index.php/journal/article/view/365
Section
Original Articles