dc.creator | Manta, S. | en |
dc.creator | Tzioumaki, N. | en |
dc.creator | Tsoukala, E. | en |
dc.creator | Panagiotopoulou, A. | en |
dc.creator | Pelecanou, M. | en |
dc.creator | Balzarini, J. | en |
dc.creator | Komiotis, D. | en |
dc.date.accessioned | 2015-11-23T10:38:48Z | |
dc.date.available | 2015-11-23T10:38:48Z | |
dc.date.issued | 2009 | |
dc.identifier | 10.1016/j.ejmech.2009.06.013 | |
dc.identifier.issn | 0223-5234 | |
dc.identifier.uri | http://hdl.handle.net/11615/30672 | |
dc.description.abstract | The beta-protected nucleosides of uracil (2a), 5-fluorouracil (2b), thymine (2c), N-4-benzoyl cytosine (2d) and N-6-benzoyl adenine (2e) were synthesized by condensation of the peracetylated 3-deoxy-3-fluoro-D-glucopyramose (1) with the corresponding silylated bases. The nucleosides were deacetylated and several subsequent protection and deprotection steps afforded the partially acetylated analogues 6a-e. Selective iodination followed by hydrogenation gave the acetylated dideoxy analogues of uracil (8a), 5-fluorouracil (8b), thymine (8c), N-4-benzoyl cytosine (8d) and N-6-benzoyl adenine (8e), respectively. Finally, direct oxidation of the free hydroxyl group at the 4'-position of 8a-e, and simultaneous elimination reaction of the beta-acetoxyl group, afforded the desired unsaturated 2,6-dideoxy-3-fluoro-4-keto-beta-D-glucopyranosyl derivatives 9a-e. The new analogues were evaluated for antiviral and cytostatic activity. Compounds 9a-e were not active against a broad panel of DNA and RNA viruses at subtoxic concentrations. However, they were markedly cytostatic against a variety of tumor cell lines. The compounds should be regarded as potential new lead compounds to be further investigated for anticancer therapy. (C) 2009 Elsevier Masson SAS. All rights reserved. | en |
dc.source | European Journal of Medicinal Chemistry | en |
dc.source.uri | <Go to ISI>://WOS:000271225800062 | |
dc.subject | Unsaturated dideoxy fluoro ketonucleosides | en |
dc.subject | beta-Elimination reaction | en |
dc.subject | Antiviral | en |
dc.subject | Antitumor activity | en |
dc.subject | BIOLOGICAL EVALUATION | en |
dc.subject | ANTIVIRAL ACTIVITY | en |
dc.subject | ANTI-HIV | en |
dc.subject | 1,5-ANHYDROHEXITOL | en |
dc.subject | NUCLEOTIDES | en |
dc.subject | CONFORMATIONAL-ANALYSIS | en |
dc.subject | KETO-NUCLEOSIDES | en |
dc.subject | DRUG-RESISTANCE | en |
dc.subject | REAGENT SYSTEM | en |
dc.subject | HYDROXY-GROUP | en |
dc.subject | IODO-GROUP | en |
dc.subject | Chemistry, Medicinal | en |
dc.title | Unsaturated dideoxy fluoro-ketopyranosyl nucleosides as new cytostatic agents: A convenient synthesis of 2,6-dideoxy-3-fluoro-4-keto-beta-D-glucopyranosyl analogues of uracil, 5-fluorouracil, thymine, N-4-benzoyl cytosine and N-6-benzoyl adenine | en |
dc.type | journalArticle | en |