Add time:09/09/2019         Source:sciencedirect.com

1-alkyl-2-pyridones, 2a-c, and 2-acyl-2-hydroxypyridines, 3a-b, were synthesized under ultrasonic irradiation. The synthesized compounds were characterized by 1HNMR and FTIR spectroscopy. DFT calculations were performed in order to study reactivity of the N and O-sites of 2-hydroxypyridine towards these reactions. The results showed that the electrophilicity index of the alkyl and acyl halide were found to be higher than that of 2-hydroxypyridine. Furthermore, these compounds were screened for antimicrobial activities and were found to be significantly inhibit bacterial and fungal strains. 1-hexyldecyl-2-pyridone (2c) and 2-acyl-2-hydroxypyridines (3a) displayed strong antibacterial activities towards Micrococcus luteus ATCC 10240 and Enterococcus faecalis ATCC 2921. Moreover compound 3a was found to effective inhibit Aspergillus fumigatus ATCC 204305 and Saccharomyces cerevisiae ATCC 9763. Hence to further validate the binding of these compounds, molecular docking studies were performed. The results revealed that compounds 2c and 3a were found to be interactive within the active sites of E. coli DNA gyrase enzyme and cytochrome P450, 14-α-sterol demethylase (CYP51) with good binding affinities. Furthermore, their comparative molecular docking results suggested to the compound 2c have a higher binding affinity than 3a with the selected receptors.

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