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 C_Me-H.....Br/C_ph-H.....O and H…π_CC. 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

Elsevier

Publisher Country

Netherlands

Indexing

Thomson Reuters

Impact Factor

3.8

Publication Type

Both (Printed and Online)

Volume

1313

Year

2024

Pages

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