title: Synthesis and biological evaluation of branched and conformationally restricted analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd).
abstract: The synthesis of branched and conformationally restricted analogs of the anticancer nucleosides 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd) is presented. Molecular modeling and (1)H NMR coupling constant analysis revealed that the furanose rings of all analogs except the LNA analog are conformationally biased towards South conformation, and are thus mimicking the structure of ECyd. All target nucleosides were devoid of anti-HIV or anticancer activity.
authors.affiliation: Nucleic Acid Center, Department of Chemistry, University of Southern Denmark, DK-5230 Odense M, Denmark.
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Hrdlicka
authors.forename: Nicolai K
authors.initials: NK
authors.lastname: Andersen
authors.forename: Jan S
authors.initials: JS
authors.lastname: Jepsen
authors.forename: Flemming G
authors.initials: FG
authors.lastname: Hansen
authors.forename: Kim F
authors.initials: KF
authors.lastname: Haselmann
authors.forename: Claus
authors.initials: C
authors.lastname: Nielsen
authors.forename: Jesper
authors.initials: J
authors.lastname: Wengel
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002460:Cell Line; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D018360:Crystallography, X-Ray; D003562:Cytidine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology*; D006801:Humans; D008958:Models, Molecular; D018716:Molecular Mimicry; D009690:Nucleic Acid Conformation; D014529:Uridine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D019380:Anti-HIV Agents; D000970:Antineoplastic Agents; D003562:Cytidine; D014529:Uridine