title: Stereocontrolled facile synthesis and biological evaluation of (3'S) and (3'R)-3'-amino (and Azido)-3'-deoxy pyranonucleosides.
abstract: This article describes the synthesis of (3 'S) and (3 'R)-3 '-amino-3 '-deoxy pyranonucleosides and their precursors (3 'S) and (3 'R)-3 '-azido-3 '-deoxy pyranonucleosides. Azidation of 1,2:5,6-di-O-isopropylidene-3-O-toluenesulfonyl-α-D-allofuranose followed by hydrolysis and subsequent acetylation afforded 3-azido-3-deoxy-1,2,4,6-tetra-O-acetyl-D-glucopyranose, which upon coupling with the proper silylated bases, deacetylation, and catalytic hydrogenation, obtained the target 3 '-amino-3 '-deoxy-β-D-glucopyranonucleosides. The desired 1-(3 '-amino-3 '-deoxy-β-D-allopyranosyl)5-fluorouracil was readily prepared from the suitable imidazylate sugar after azidation followed by a protection/deprotection sequence and reduction of the unprotected azido precursor. No antiviral activity was observed for the novel nucleosides. Moderate cytostatic activity was recorded for the 5-fluorouracil derivatives.
authors: Laboratory of Bio-Organic Chemistry Department of Biochemistry and Biotechnology, University of Thessaly, Larissa, Greece.
authors: Stella
authors: S
authors: Manta
authors: Vanessa
authors: V
authors: Parmenopoulou
authors: Christos
authors: C
authors: Kiritsis
authors: Athina
authors: A
authors: Dimopoulou
authors: Nikolaos
authors: N
authors: Kollatos
authors: Ioannis
authors: I
authors: Papasotiriou
authors: Jan
authors: J
authors: Balzarini
authors: Dimitri
authors: D
authors: Komiotis
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D005472:Fluorouracil / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D009369:Neoplasms / Q000188:drug therapy; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D014777:Virus Diseases / Q000188:drug therapy; D014780:Viruses / Q000187:drug effects
chemical_list: D000970:Antineoplastic Agents; D000998:Antiviral Agents; D001386:Azides; D009705:Nucleosides; D011714:Pyrans; D005472:Fluorouracil