New flavonoid glycosides conjugates: synthesis, characterization, and evaluation of their cytotoxic activities

Abstract

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 deprotectionof the acetyl protective groups afforded the desired 3-O-flavonoids glycosides in satisfactory yields. All the preparedcompounds 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-activityrelationship study showed that the introduction of glycoside moiety at the C-3 OH position does not improve thebioactivity.