Synthesis and study of the antimicrobial activity of N-alkyl(dimethylaminoalkoxyacetammoniumchloride)-N′-[4-(hydroxymethyl)-1H-pyrazol-3-yl]ureas

M. K. Bratenko, M. M. Barus, I. P. Burdenyuk, M. V. Vovk

Abstract


A number of the quaternary ammonium salts previously unknown with polyfunctional pyrazole base have been obtained. The structure of these pyrazoles contains highly polar ammonium, ureide and hydroxymethyl groups. The compounds under study were synthesized by quaternization of N-dimethylaminoalkyl-N 4- ]-׳ (hydroxymethyl)-1H-pyrazol-3-yl]ureas by chloroacetic acid esters containing the lipophilic alcohol residue of various length. The structure of the substances obtained has been strictly confirmed by the data of elemental analysis, as well as by IR- and NMR 1H-spectral measurements. A wide range of the antimicrobic action for each substance synthesized has been found in their microbiological study. Gram-positive microorganisms, in particular coccal bacteria group, revealed the highest sensitivity to the inhibiting action of the substances. The culture of yeast-like fungi f Candida genus was less sensitive. Quaternary ammonium salts had less expressed action on gram-negative bacteria of enteritis group, e.g. E. coli, Proteus vulgaris and Pseudomona saeruginosa. Analysis of the structureactivity relationship of a number of compounds makes clear that the length of the alkoxyacetyl fragment near the ammonium centre has the greatest effect on the antimicrobic action. At the same time there is virtually no dependence of the biological effect from the distance between ureide and amide nitrogen atoms in the exocyclic fragment. The study of the antimicrobic action depletion of the most active substances by tenfold addition of inoculation doses of test cultures of St. aureus has shown their cumulatively high bactericidal action.  


Keywords


N-dimethylaminoalkyl-N 4- ]-׳ (hydroxymethyl)-1H-pyrazol-3-yl]-ureas; chloroacetic acid esters; N-alkyl(dimethylalkoxyacetammonium chloride)-N 4- ]-׳ (hydroxymethyl)-1H-pyrazol-3-yl]ureas; antimicrobic activity

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DOI: https://doi.org/10.24959/ophcj.14.813

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

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