Synthesis, XRD/HSA-interactions, synthon, TD-DFT/optical analysis, docking and antibacterial evaluation of two (±)-Isoflavonoid derivatives

A high -yield synthesis of the new racemic (+/-)-2-(1-bromoethyl)-7-methoxy-3-(4-methoxyphenyl)-4H-chromen4-one was achieved in two steps by O - and 2C -methylation 7,4 ' -dihydroxy-2-methylisoflavone, followed by radical bromination of the allylic methylene moiety using N -bromosuccinimide. XRD-crystallography, NMR, UV - vis CHN-EA, and FT -IR were all used to establish the identity and structure of the target ligand. Both the XRD, Hirshfeld surface area (HSA) and the DFT structural optimization validated the (+/-)-bromo-chromen-4-one structural formula. XRD analysis reveals two types of synthons due to the presence of multiple short interactions, including C Me -H Br/C ph -H O and H ... pi C -- C . There is a high harmony between the experimental XRDstructural parameters and their DFT counterparts; additionally, the optical characteristics were derived by comparing the experimental UV - Vis result to the TD-DFT/B3LYP and TD-DFT/CAM-B3LYP ones. The compounds capacity to bind to DNA was assessed via the molecular docking technique with the use of 1BNA. The antibacterial activity of the produced (+/-)-bromo-chroman-4-one and (+/-)-the non bromo-chroman-4-one derivatives was evaluated against eight bacterial strains.