title: Synthesis of novel thiopurine pyranonucleosides: evaluation of their bioactivity.
abstract: We report the synthesis of novel thiopurine pyranonucleosides. Direct coupling of silylated 6-mercaptopurine and 6-thioguanine with the appropriate pyranoses 1a-e via Vorbrüggen nucleosidation, gave the N-9 linked mercaptopurine 2a-e and thioguanine 4a-e nucleosides, while their N-7 substituted congeners 10a-e and 7a-e, were obtained through condensation of the same acetates with 6-chloro and 2-amino-6-chloropurines, followed by subsequent thionation. Nucleosides 3a-e, 5a-e, 8a-e, and 11a-e were evaluated for their cytostatic activity in three different tumor cell proliferative assays.
authors.affiliation: a Department of Biochemistry and Biotechnology, Laboratory of Bioorganic Chemistry , University of Thessaly , Larissa , Greece.
authors.forename: Athina
authors.initials: A
authors.lastname: Dimopoulou
authors.forename: Stella
authors.initials: S
authors.lastname: Manta
authors.forename: Vanessa
authors.initials: V
authors.lastname: Parmenopoulou
authors.forename: Petros
authors.initials: P
authors.lastname: Gkizis
authors.forename: Evdoxia
authors.initials: E
authors.lastname: Coutouli-Argyropoulou
authors.forename: Dominique
authors.initials: D
authors.lastname: Schols
authors.forename: Dimitri
authors.initials: D
authors.lastname: Komiotis
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D006801:Humans; D020128:Inhibitory Concentration 50; D051379:Mice; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D011684:Purine Nucleosides
keywords: 2-amino-6-chloropurine; 6-Mercaptopurine; 6-chloropurine; 6-thioguanine; cytotoxic activity; pyranonucleosides