title: Synthesis and biological evaluation of 2'-substituted-4'-selenoribofuranosyl pyrimidines as antitumor agents.
abstract: The 2'-substituted-4'-selenoribofuranosyl pyrimidines 3a-3j were synthesized from D-ribose and assayed for anticancer activity. The 2'-azido and 2'-fluoro groups with a ribo configuration were introduced by the regioselective opening of the O2,2'-anhydronucleosides with sodium azide and (HF)x-pyridine, respectively. Among the compounds tested, only 2'-fluoro derivative 3j was found to exhibit significant anticancer activity, but was much less potent than the corresponding 2'-arabino analogue 2c. This study will provide medicinal chemists with the insight into the identification of structural requirements for the anticancer activity for the developments of biologically active nucleosides.
authors.affiliation: College of Pharmacy, Ewha Womans University, Seoul, 120-750, Korea.
authors.forename: Varughese
authors.initials: V
authors.lastname: Alexander
authors.forename: Jayoung
authors.initials: J
authors.lastname: Song
authors.forename: Jinha
authors.initials: J
authors.lastname: Yu
authors.forename: Jung Hee
authors.initials: JH
authors.lastname: Choi
authors.forename: Jin-Hee
authors.initials: JH
authors.lastname: Kim
authors.forename: Sang Kook
authors.initials: SK
authors.lastname: Lee
authors.forename: Won Jun
authors.initials: WJ
authors.lastname: Choi
authors.forename: Lak Shin
authors.initials: LS
authors.lastname: Jeong
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001386:Azides; D045744:Cell Line, Tumor; D015195:Drug Design; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000494:pharmacology*; D011725:Pyridines / Q000138:chemical synthesis* / Q000494:pharmacology*; D011744:Pyrimidinones / Q000138:chemical synthesis* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D001386:Azides; D007202:Indicators and Reagents; D016566:Organoselenium Compounds; D011725:Pyridines; D011744:Pyrimidinones