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 Volume 1313, 5 October 2024, 138700

Publisher

Elsevier

Publisher Country

Netherlands

Indexing

Scopus

Impact Factor

None

Publication Type

Both (Printed and Online)

Volume

1313

Year

2024

Pages

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