A high-yield synthesis of the new racemic (±)-2-(1-bromoethyl)-7-methoxy-3-(4-
methoxyphenyl)-4H-chromen-4-one was achieved in two steps by O- and 2-C-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 CMeH.....Br/Cph-H.....O and H...πC=C. There is a high harmony between the experimental XRD-structural
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.
 

Title

Journal of Molecular Structure

Publisher

Journal of Molecular Structure

Publisher Country

Palestine

Publication Type

Both (Printed and Online)

Volume

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Year

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Pages

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