The synthesis of 7-O-carboxymethyl-4'-fluoroisoflavone 4 and 7-O-carboxymethyl-4'-fluoro-2-trifluormethylisoflavone 7 involved the cyclization of 2,4-dihydroxy-4'-fluoro deoxybenzoin 1, followed by 7-O-alkylation with methyl bromoacetate and subsequent acid-catalyzed hydrolysis. The structures of the novel compounds were validated using a range of techniques, including XRD crystallography (1H, 19F, 13C)-NMR, and IR. Only inter- halogen contacts were detected in 5, while they were completely lacking in 2 and 4, owing to the presence of crystalline ethanol in the crystal structure. The %F. . .F in 5 was 12.2% based on Hirshfeld calculations. The aromatic π-π stacking interactions were important only in 2 and 4 but not observed in 5. Isoflavones 4, 5, and 7 displayed anticancer activity against MCF-7 cancer cells, with IC50 values of 13.66, 15.43, and 11.73 µM, respectively.

Title

molecules

Publisher

MDPI

Publisher Country

Palestine

Publication Type

Prtinted only

Volume

30

Year

2025

Pages

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