| Abstract [eng] |
In this work, methyl-2-hydroxy-2-sulfanylidene-2,3-dihydro-1H-imidazol-1-yl]benzoates 4a,b and 2-hydroxy-5-[4-(naphthalen-2-yl)-2-sulfanylidene-2,3-dihydro-1H-imidazol-1-yl]benzhydrazide 5a were synthesized from 5-aminosalicylic acid. S-alkylation reactions of methyl-2-hydroxy-2 sulfanylidene-2,3-dihydro-1H-imidazol-1-yl]benzoates 4a,b with various 2-bromoacetophenones and ethyl chloroacetate were further performed. Reactions of 2-hydroxy-5-[4-(naphthalen-2-yl)-2-sulfanylidene-2,3-dihydro-1H-imidazol-1 yl]benzhydrazide 5a with ethyl chloroacetate, hexane-2,5-dione and ethyl chloroacetate were carried out to form a compound with a pyrrole fragment, as well as condensation reactions with various benzaldehydes to form hydrazones. The reaction of the hydrazide with pantane-2,5-dione and ethyl chloroacetate failed to yield a product with a pyrazole fragment. Antibacterial tests were performed with newly synthesized compounds against E. coli and B. subtilis bacteria. Compounds 5a, 6a, 8a, 9a and 17a showed the best antibacterial activity. The in-silico ADMET evaluation was performed on these compounds to evaluate their physicochemical, pharmacokinetic, bioavailability and toxicity theoretical parameters. Compounds 6a, 8a, and 9a demonstrated the most balanced bioavailability profile, while compound 17a exhibited the most favorable predicted toxicological profile. Molecular docking experiments were conducted to explore the binding affinities and interaction modalities of selected derivatives with the target PDB-1kzn protein. 28 new compounds were synthesized in the work. The structure of the obtained compounds was confirmed by NMR, FTIR and elemental analysis methods, and the melting point of the compounds was determined. |
