dc.creator | Tsoukala, E. | en |
dc.creator | Tzioumaki, N. | en |
dc.creator | Manta, S. | en |
dc.creator | Riga, A. | en |
dc.creator | Balzarini, J. | en |
dc.creator | Komiotis, D. | en |
dc.date.accessioned | 2015-11-23T10:52:26Z | |
dc.date.available | 2015-11-23T10:52:26Z | |
dc.date.issued | 2010 | |
dc.identifier | 10.1016/j.bioorg.2010.08.001 | |
dc.identifier.issn | 0045-2068 | |
dc.identifier.uri | http://hdl.handle.net/11615/34077 | |
dc.description.abstract | The 3-deoxy-3-fluoro-6-S-(2-S-pyridyl)-6-thio-beta-D-glucopyranosyl nucleoside analogs 7 were prepared via two facile synthetic routes. Their precursors, 3-fluoro-6-thio-glucopyranosyl nucleosides 5a-e, were obtained by the sequence of deacetylation of 3-deoxy-3-fluoro-beta-D-glucopyranosyl nucleosides 2a-e, selective tosylation of the primary OH of 3 and finally treatment with potassium thioacetate. The desired thiolpyridine protected analogs 7a-c,f,g were obtained by the sequence of deacetylation of 5a-c followed by thiopyridinylation and/or condensation of the corresponding heterocyclic bases with the newly synthesized peracetylated 6-S-(2-S-pyridyl) sugar precursor 13, which was obtained via a novel synthetic route from glycosyl donor 12. None of the compounds 6 and 7 showed antiviral activity, but the 5-fluorouracil derivative 7c and particularly the uracil derivative 7b were endowed with an interesting and selective cytostatic action against a variety of murine and human tumor cell cultures. (C) 2010 Elsevier Inc. All rights reserved. | en |
dc.source.uri | <Go to ISI>://WOS:000285403000025 | |
dc.subject | 3-Fluoro-6-S-(2-S-pyridyl) nucleosides | en |
dc.subject | Thiopyridinylation | en |
dc.subject | Cytostatic | en |
dc.subject | agents | en |
dc.subject | FLUORO-KETOPYRANOSYL NUCLEOSIDES | en |
dc.subject | BIOLOGICAL EVALUATION | en |
dc.subject | N-4-BENZOYL | en |
dc.subject | CYTOSINE | en |
dc.subject | EFFICIENT SYNTHESIS | en |
dc.subject | ANTIVIRAL AGENTS | en |
dc.subject | UNSATURATED | en |
dc.subject | EXOMETHYLENE | en |
dc.subject | RIBONUCLEOTIDE REDUCTASE | en |
dc.subject | FLUORINATED NUCLEOSIDES | en |
dc.subject | ANALOGS | en |
dc.subject | DERIVATIVES | en |
dc.subject | Biochemistry & Molecular Biology | en |
dc.subject | Chemistry, Organic | en |
dc.title | Synthesis of 3-fluoro-6-S-(2-S-pyridyl) nucleosides as potential lead cytostatic agents | en |
dc.type | journalArticle | en |