The synthesis and the antimicrobial activity of the substituted aryl amides of 3-arylmethyl-2,4- dioxo-1,3,7-triazaspiro[4.4]nonane-7-carboxylic acids

K. Yu. Krolenko, S. V. Vlasov, O. D. Vlasova, I. O. Zhuravel

Abstract


By the interaction of the substituted aryl isocyanates with the series of 3-arylmethyl-1,3,7-triazaspiro[ 4.4]nonane-2,4-diones in the propanol-2 medium the series of the substituted aryl amides of 3-arylmethyl-2,4-dioxo-1,3,7-triazaspiro[4.4]nonane-7-carboxylic acids have been obtained. The structure of the products obtained has been confirmed by the instrumental methods of the analysis, such as 1Н, 13С NMR- and chromato-mass spectrometry. The 1Н NMR-spectra of all of the substances obtained contain the signal of the methylene group of the arylmethyl fragment at 4.5 ppm as a singlet; the number and splitting of the signal in the range of the aromatic protons resonance well corresponds with the substitution in the aromatic part of the molecule; the protons of the NHCO urea fragment with the signal of the NH at position 1 are observed as two singlet signals at 7.4-8.2 and 8.9 ppm. The 13C NMR-spectra of all compounds obtained contain four signals at 35, 45, 54 and 65 ppm of the pyrrolidine cycle of the molecules; three signals of the carbonyl groups carbon atoms are observed at 154, 155 and 174 ppm. The LC-MS spectra of the target compounds contain the peaks of [M+H]+ ions, which masses are in good accordance with the structures proposed. The results of the antimicrobial activity screening show the ability of the compounds synthesized to inhibit the growth of the Candida albicans fungi strain. The gram-positive microorganisms such as the strains of Staphylococcus aureus and Bacillus subtilis are found to be sensitive to the compounds containing the methyl groups as substituents in the arylmethyl fragments of the molecule.


Keywords


hydantoin; urea; pyrrolidone; antimicrobial agents

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References


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GOST Style Citations






DOI: https://doi.org/10.24959/93482

Abbreviated key title: Vìsn. farm.

ISSN 2415-8844 (Online), ISSN 1562-7241 (Print)