Synthesis and Spectroscopic Characterization of Novel Pyridine-based N-acyl Hydrazone Derivatives and Molecular Docking Studies on Glucosamine-6-Phosphate

Authors : Derya VURAL, Selbi KESKİN

Pages : 135-152

Doi:10.31466/kfbd.1184337

View : 13 | Download : 8

Publication Date : 2023-03-15

Article Type : Research Paper

Abstract :Antimicrobial resistance in infectious diseases caused by organisms such as bacteria, fungi, viruses, and parasites has led to an increase in studies and demands for new antimicrobial drug development. The compounds including pyridine and N-acylhydrazone skeletons in their structures have a large application area in drug discovery due to their anticancer, anti-tubercular, anti-bacterial and anti-fungal activities. Here, the novel N-acyl-hydrazone derivatives, insert ignore into journalissuearticles values(E);-2-oxo-N\`-insert ignore into journalissuearticles values(2,3,4-trimethoxybenzylidene);-1,2-dihydropyridine-3-carbohydrazide and insert ignore into journalissuearticles values(E);-N\`-insert ignore into journalissuearticles values(1-insert ignore into journalissuearticles values(4-bromophenyl); ethylidene);-2-oxo-1,2-dihydropyridine-3-carbohydrazide were synthesized through a multistep reaction sequence. The structures of newly synthesized compounds were established on the basis of IR, 1D and 2D NMR spectra and mass spectral data. The theoretical electronic structure analysis was performed by density functional theory insert ignore into journalissuearticles values(DFT); at the B3LYP level with the 6-311++Ginsert ignore into journalissuearticles values(d,p); basis set in the gas phase of synthesized compounds. The newly synthesized compounds were docked on glucosamine-6 phosphate synthase to determine potential interactions between the analyzed compounds and its active site due to its role in microbial cell wall synthesis. The possibilities of these compounds to being active for antimycobacterial and antituberculosis have been found as quite high, and their interactions in the binding site have been determined with the range of binding affinity, [-7.1, -7.3] kcal/mol, respectively.
Keywords : N açil hidrazon, azot içeren heterohalkalı bileşikler, moleküler yerleştirme, glukozamin 6 fosfat