The synthesis, spectral properties and the biological activity of 7-arenesulfonyl-3-arylmethyl-1,3,7-triazaspiro[4.4]nonane-2,4-dione derivatives
DOI:
https://doi.org/10.24959/nphj.17.2149Keywords:
hydantoin, sulfonamides, pyrrolidone, antibacterial agentsAbstract
Aim. To synthesize the series of 7-arenesulfonyl-3-arylmethyl-1,3,7-triazaspiro[4.4]nonane-2,4-dione, to study their spectral properties and antibacterial activity.
Materials and methods. The methods of organic synthesis, instrumental methods of organic compounds analysis, as well as the agar diffusion method were used.
Results and discussion. By the interaction of 3-arymethyl-1,3,7-triazaspiro[4.4]nonane-2,4-diones with arenesulfonyl cholrides in the presence of triethylamine the series of 7-arenesulfonyl-3-arylmethyl-1,3,7-triazaspiro[4.4]nonane-2,4-dione was obtained. For the compounds containing the fragments of 1-sulfonylamido-(2,4)- and 3,4-difluorobenzene the 1H-1H coupling constants in their 1H{19F}-NMR fluorine decoupled spectra, as well as the 19F-19F coupling constants in the 19F{1H}-NMR proton decoupled spectra were measured. The antimicrobial activity screening showed that the growth of such bacterial strains as Staphylococcus aureus and Bacillus subtilis was inhibited by the compounds of the series obtained.
Conclusions. It has been found that the interaction of 3-arymethyl-1,3,7-triazaspiro[4.4]nonane-2,4-diones with arenesulfonyl cholrides is an effective way for the synthesis of 7-arenesulfonyl-3-arylmethyl-1,3,7-triazaspiro[4.4]nonane-2,4-diones with the promising biological activity against the strains of gram-positive bacteria such as Staphylococcus aureus and Bacillus subtilis. Among 7-arenesulfonyl-3-arylmethyl-1,3,7-triazaspiro[4.4]nonane-2,4-dione derivatives 3-(3-methylbenzyl)-7-(toluene-4-sulfonyl)-1,3,7-triazaspiro[4.4]nonane-2,4-dione exhibited the highest activity.
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