title: Synthesis of genistein 2,3-anhydroglycoconjugates -- potential antiproliferative agents.
abstract: The title compounds, variously protected 2.3-anhydrosugars linked with genistein through an alkyl chain, were synthesized in a sequence of reactions. First step involved Ferrier rearragement of 3,4-di-O-acetyl-L-rhamnal with 3-bromopropanol to obtain 2,3-unsaturated bromoalkylglycosides. The next step was epoxidation with m-CPBA and finally these compounds were connected with genistein in reaction of 7-O-genistein tetra-butylamonium salt with 2,3-anhydro bromoalkylglycosides. Obtained glycoconjugates differ in orientation of an oxirane ring and the protecting group in a sugar moiety. All compounds were tested in vitro for antiproliferative potential in cancer cells.
authors.affiliation: Silesian University of Technology, Faculty of Chemistry, Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Gliwice, Poland. katarzyna.goj@polsl.pl
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Goj
authors.forename: Aleksandra
authors.initials: A
authors.lastname: Rusin
authors.forename: Wiesław
authors.initials: W
authors.lastname: Szeja
authors.forename: Radosław
authors.initials: R
authors.lastname: Kitel
authors.forename: Roman
authors.initials: R
authors.lastname: Komor
authors.forename: Grzegorz
authors.initials: G
authors.lastname: Grynkiewicz
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D049109:Cell Proliferation / Q000187:drug effects*; D019833:Genistein / Q000031:analogs & derivatives* / Q000494:pharmacology; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000494:pharmacology; D045325:HCT116 Cells; D006801:Humans
chemical_list: D000970:Antineoplastic Agents; D006001:Glycoconjugates; D019833:Genistein