title: New carbocyclic nucleoside analogues with a bicyclo[2.2.1]heptane fragment as sugar moiety; synthesis, X-ray crystallography and anticancer activity.
abstract: An amine group was synthesized starting from an optically active bicyclo[2.2.1]heptane compound, which was then used to build the 5 atoms ring of a key 6-chloropurine intermediate. This was then reacted with ammonia and selected amines obtaining new adenine- and 6-substituted adenine conformationally constrained carbocyclic nucleoside analogues with a bicyclo[2.2.1]heptane skeleton in the sugar moiety. X-ray crystallography confirmed an exo-coupling of base to the ring and a L configuration of the nucleoside analogues. The compounds were tested for anticancer activity.
authors.affiliation: National Institute for Chemical-Pharmaceutical Research and Development, 112 Vitan Av., 031299 Bucharest 3, Romania. Electronic address: cvtanase@gmail.com.
authors.forename: Constantin I
authors.initials: CI
authors.lastname: Tănase
authors.affiliation: Organic Chemistry Center "C.D.Neniţescu", 202 B Splaiul Independentei, Bucharest 060023, Romania.
authors.forename: Constantin
authors.initials: C
authors.lastname: Drăghici
authors.affiliation: Organic Chemistry Center "C.D.Neniţescu", 202 B Splaiul Independentei, Bucharest 060023, Romania.
authors.forename: Miron Teodor
authors.initials: MT
authors.lastname: Căproiu
authors.affiliation: Institute of Macromolecular Chemistry "Petru Poni", Iasi, Romania.
authors.forename: Sergiu
authors.initials: S
authors.lastname: Shova
authors.affiliation: Laboratoire de Chimie Organique Biomoléculaire de Synthèse, UMR 5625 CNRS-Université Montpellier II, Place Eugène Bataillon, 34095 Montpellier Cedex 5, France.
authors.forename: Christophe
authors.initials: C
authors.lastname: Mathe
authors.affiliation: National Institute for Chemical-Pharmaceutical Research and Development, 112 Vitan Av., 031299 Bucharest 3, Romania.
authors.forename: Florea G
authors.initials: FG
authors.lastname: Cocu
authors.affiliation: Central Laboratory for Phytosanitary Quarantine, 11, Voluntari Blvd., 077190 Voluntari, Romania.
authors.forename: Cristian
authors.initials: C
authors.lastname: Enache
authors.affiliation: Organic Chemistry Center "C.D.Neniţescu", 202 B Splaiul Independentei, Bucharest 060023, Romania.
authors.forename: Maria
authors.initials: M
authors.lastname: Maganu
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000627:therapeutic use; D018360:Crystallography, X-Ray; D006536:Heptanes / Q000737:chemistry*; D006801:Humans; D008968:Molecular Conformation; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D006536:Heptanes; D009705:Nucleosides
keywords: Amine; Anticancer; Azide; Bicyclo[2.2.1]heptane nucleosides; Chloropurine; X-ray crystallography