Abstract <p>A series of dicoumarinyl bipyridines were synthesized via a two-step approach involving Wittig reaction of formyl pyridines with appropriate coumarinoyl phosphonium ylides, followed by Krohnke reaction with coumarinoyl pyridinium bromide salt. The compounds were characterized with analytical and spectroscopic techniques such as IR, ¹H, ¹³C NMR as well as mass spectrometry. The antimicrobial inhibition activity of the reported compounds was screened and compound 2′′′-[6′-(4-methyl-2-oxo-3-phenyl-2<i>H</i>-chromen-6-yl)-(2′′,4′-bipyridin)-2′-yl]-3′′′<i>H</i>-benzo[<i>f</i>]chromen-3′′′-one exhibited the highest antibacterial inhibition. The structure-activity relationship (SAR) of the synthesized compounds was examined in correlation with their antibacterial activity. Molecular structure optimization for all derivatives was carried out using Density Functional Theory (DFT) at the B3LYP level with the 6-311G(d,p) basis set. Furthermore, global reactivity descriptors were computed and analyzed to understand their relationship with the observed biological activity. Molecular docking studies revealed that the synthesized compounds exhibited notable binding affinities indicating strong interactions with the target proteins. The synthesized compounds were also subjected to <i>in silico</i> ADMET analysis.</p>