A series of novel halogenated 3-hydroxyflavones (3HFs) were prepared by reacting halogenated hydroxyacetophenones with the appropriate aromatic aldehyde. Glycosylation of 3HFs with acetobromoglucose and deprotection of the acetyl protective groups afforded the desired 3-$O$-flavonoids glycosides in satisfactory yields. All the prepared compounds were tested for their cytotoxic activity against HCT-116, MCF-7, and OVCAR-3 human cancer cell lines. The 3HFs exhibited higher cytotoxic activities compared with the glycosylated flavonoids. Overall, the structure-activity relationship study showed that the introduction of glycoside moiety at the C-3 OH position does not improve the bioactivity.
SOUIEI, SAWSSEN; GARAH, FATIMA BOUSEJRA-EL; BELKACEM, MOHAMED AMINE; ZNATI, MANSOUR; BOUAJILA, JALLOUL; and JANNET, HICHEM BEN
"New flavonoid glycosides conjugates: synthesis, characterization, and evaluation of their cytotoxic activities,"
Turkish Journal of Chemistry: Vol. 43:
2, Article 3.
Available at: https://journals.tubitak.gov.tr/chem/vol43/iss2/3