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Branched-chain C-cyano pyranonucleosides: Synthesis of 3 '-C-cyano & 3 '-C-cyano-3 '-deoxy pyrimidine pyranonucleosides as novel cytotoxic agents
dc.creator | Kiritsis, C. | en |
dc.creator | Manta, S. | en |
dc.creator | Parmenopoulou, V. | en |
dc.creator | Balzarini, J. | en |
dc.creator | Komiotis, D. | en |
dc.date.accessioned | 2015-11-23T10:34:53Z | |
dc.date.available | 2015-11-23T10:34:53Z | |
dc.date.issued | 2011 | |
dc.identifier | 10.1016/j.ejmech.2011.08.033 | |
dc.identifier.issn | 0223-5234 | |
dc.identifier.uri | http://hdl.handle.net/11615/29430 | |
dc.description.abstract | This report describes the total and facile synthesis of 3'-C-cyano & 3'-C-cyano-3'-deoxy pyrimidine pyranonucleosides. Reaction of 3-keto glucoside 1 with sodium cyanide gave the desired precursor 3-C-cyano-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose (2). Hydrolysis followed by acetylation led to the 1,2,3,4,6-penta-O-acetyl-3-C-cyano-D-glucopyranose (4). Compound 4 was condensed with silylated 5-fluorouracil, uracil, thymine and N-4-benzoylcytosine, respectively and deacetylated to afford the target 1-(3'-C-cyano-beta-D-glucopyranosyl)nucleosides 6a-d. Routine deoxygenation at position 3' of cyanohydrin 2, followed by hydrolysis and acetylation led to the 3-C-cyano-3-deoxy-1,2,4,6-tetra-O-acetyl-D-allopyranose (10). Coupling of sugar 10 with silylated pyrimidines and subsequent deacetylation yielded the target 1-(3'-C-cyano-3'-deoxy-beta-D-allopyranosyl)nucleosides 12a-d. The new analogues were evaluated for their antiviral and cytostatic activities. It was found that 6a was endowed with a pronounced anti-proliferative activity that was only 2- to 8-fold less potent than that shown for the parental base 5-fluorouracil. None of the compounds showed activity against a broad panel of DNA and RNA viruses. (C) 2011 Elsevier Masson SAS. All rights reserved. | en |
dc.source.uri | <Go to ISI>://WOS:000298120500046 | |
dc.subject | C-cyano pyranonucleosides | 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 | 1,5-ANHYDROHEXITOL NUCLEOTIDES | en |
dc.subject | CONFORMATIONAL-ANALYSIS | en |
dc.subject | N-6-BENZOYL ADENINE | en |
dc.subject | ANTIVIRAL ACTIVITY | en |
dc.subject | DERIVATIVES | en |
dc.subject | MECHANISM | en |
dc.subject | ANALOGS | en |
dc.subject | Chemistry, Medicinal | en |
dc.title | Branched-chain C-cyano pyranonucleosides: Synthesis of 3 '-C-cyano & 3 '-C-cyano-3 '-deoxy pyrimidine pyranonucleosides as novel cytotoxic agents | en |
dc.type | journalArticle | en |
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