Synthesis, in vitro antimicrobial evaluation and computational insights into new bipyridinyl-coumarin hybrids
摘要
A series of bipyridinyl-coumarin hybrids 5a-i was synthesized via a sequential approach involving the Wittig reaction of 7-methoxy-4-formyl coumarin with appropriate phosphonium ylides, followed by Krohnke reaction with pyridoyl methyl pyridinium iodide salts. The chemical formulae and structures of reported derivatives were obtained using different analytical and spectroscopic techniques such as IR, 1H-, 13C-NMR as well as mass spectrometry. Molecular structure optimization of all compounds 5a-i was performed by the density functional theory (DFT/B3LYP) method and the basis set 6–311 G with double zeta plus polarization (d, p). The antimicrobial inhibition activity of the reported compounds was screened and compounds 5b, 5c and 5e exhibited the highest antibacterial inhibition. The structure–activity relationship (SAR) of the synthesized compounds was correlated with their antibacterial activity. Additionally, global reactivity descriptors were analyzed in relation to the biological properties of the compounds. The molecular docking studies of synthesized compounds were carried out, and the docking analysis revealed significantly negative binding scores. The binding interaction was found to be correlated with the substituent fragments of the compounds.