dc.creator | Kollatos, N. | en |
dc.creator | Manta, S. | en |
dc.creator | Dimopoulou, A. | en |
dc.creator | Parmenopoulou, V. | en |
dc.creator | Triantakonstanti, V. V. | en |
dc.creator | Kellici, T. | en |
dc.creator | Mavromoustakos, T. | en |
dc.creator | Schols, D. | en |
dc.creator | Komiotis, D. | en |
dc.date.accessioned | 2015-11-23T10:35:13Z | |
dc.date.available | 2015-11-23T10:35:13Z | |
dc.date.issued | 2015 | |
dc.identifier | 10.1016/j.carres.2015.01.021 | |
dc.identifier.issn | 0008-6215 | |
dc.identifier.uri | http://hdl.handle.net/11615/29533 | |
dc.description.abstract | A new series of 3 '-C-trifluoromethyl- and 3 '-C-methyl-beta-D-allopyranonucleosides of 5-fluorouracil and their deoxy derivatives has been designed and synthesized. Treatment of ketosugar 1 with trifluoromethyltrimethylsilane under catalytic fluoride activation and methyl magnesium bromide, gave 1,2:5,6-di-O-isopropylidene-3-C-trifluoromethyl (2a) and 3-C-methyl (2b)-alpha-D-allofuranose, respectively, in a virtually quantitative yield and with complete stereoselectivity. Hydrolysis followed by acetylation led to the 1,2,4,6-tetra-O-acetyl-3-C-trifluoromethyl (3a) and 3-C-methyl (3b)-beta-D-allopyranose. Compounds 3a,b were then condensed with silylated 5-fluorouracil and deacetylated to afford the target nucleosides 5a,b. Deoxygenation of the peracylated allopyranoses 3a,b followed by condensation with silylated 5-fluorouracil and subsequent deacetylation yielded the target 3 '-deoxy-3 '-C-trifluoromethyl and 3 '-deoxy-3 '-C-methyl-beta-D-glucopyranonucleosides 14a,b. The newly synthesized compounds were evaluated for their potential antiviral and cytostatic activities. The 3 '-deoxy-3 '-C-methyl-ribonucleoside 11b showed significant cytotoxic activity (similar to 7 mu M) almost equally active against a variety of tumor cell lines. (C) 2015 Elsevier Ltd. All rights reserved. | en |
dc.source.uri | <Go to ISI>://WOS:000352217900024 | |
dc.subject | C-Trifluoromethyl nucleosides | en |
dc.subject | C-Methyl nucleosides | en |
dc.subject | Cytotoxicity | en |
dc.subject | 5-Fluorouracil | en |
dc.subject | FLUORO-KETOPYRANOSYL NUCLEOSIDES | en |
dc.subject | BIOLOGICAL EVALUATION | en |
dc.subject | N-4-BENZOYL | en |
dc.subject | CYTOSINE | en |
dc.subject | PYRIMIDINE PYRANONUCLEOSIDES | en |
dc.subject | UNSATURATED EXOMETHYLENE | en |
dc.subject | N-6-BENZOYL ADENINE | en |
dc.subject | ANTIVIRAL AGENTS | en |
dc.subject | ANALOGS | en |
dc.subject | DERIVATIVES | en |
dc.subject | ANTITUMOR | en |
dc.subject | Biochemistry & Molecular Biology | en |
dc.subject | Chemistry, Applied | en |
dc.subject | Chemistry, Organic | en |
dc.title | Branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3 '-C-trifluoromethyl and 3 '-C-methyl pyranonucleosides | en |
dc.type | journalArticle | en |