title: Discovery of a new template for anticancer agents: 2'-deoxy-2'-fluoro-4'-selenoarabinofuranosyl-cytosine (2'-F-4'-seleno-ara-C).
abstract: The first synthesis of 2'-deoxy-2'-fluoro-4'-selenoarabinofuranosyl pyrimidines as potent anticancer agents was accomplished using the DAST fluorination as a key step. It was first revealed that selenium atom participated in the DAST fluorination of 4'-selenonucleosides and that conformational bias induced by bulky selenium acted as a decisive factor in the DAST fluorination. Among compounds tested, 2'-F-4'-seleno-ara-C (4a) exhibited highly potent anticancer activity in all cancer cell lines tested and was more potent than ara-C (1).
authors.affiliation: Department of Bioinspired Science, Division of Life and Pharmaceutical Sciences, College of Pharmacy, Ewha Womans University, Seoul, Korea. lakjeong@ewha.ac.kr
authors.forename: Lak Shin
authors.initials: LS
authors.lastname: Jeong
authors.forename: Dilip K
authors.initials: DK
authors.lastname: Tosh
authors.forename: Won Jun
authors.initials: WJ
authors.lastname: Choi
authors.forename: Sang Kook
authors.initials: SK
authors.lastname: Lee
authors.forename: You-Jin
authors.initials: YJ
authors.lastname: Kang
authors.forename: Sun
authors.initials: S
authors.lastname: Choi
authors.forename: Jin Hee
authors.initials: JH
authors.lastname: Lee
authors.forename: Hankil
authors.initials: H
authors.lastname: Lee
authors.forename: Hyuk Woo
authors.initials: HW
authors.lastname: Lee
authors.forename: Hea Ok
authors.initials: HO
authors.lastname: Kim
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D003561:Cytarabine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D003596:Cytosine / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D055808:Drug Discovery; D054879:Halogenation; D006801:Humans; D020128:Inhibitory Concentration 50; D008958:Models, Molecular; D008968:Molecular Conformation; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: C543822:2'-deoxy-2'-fluoro-4'-selenoarabinofuranosylcytosine; D000970:Antineoplastic Agents; D016566:Organoselenium Compounds; D003561:Cytarabine; D003596:Cytosine