Efficient Consecutive Synthesis of Fluorinated Isoflavone Analogs, X-Ray Structures, Hirshfeld Analysis, and Anticancer Activity Assessment.

ABSTRACT: 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'-fluorodeoxybenzoin 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 interhalogen 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 on

SUBMITTER: Ayoup MS 

PROVIDER: S-EPMC11857983 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature