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Stereocontrolled synthesis of 4 '-C-cyano and 4 '-C-cyano-4 '-deoxy pyrimidine pyranonucleosides as potential chemotherapeutic agents

dc.creatorKiritsis, C.en
dc.creatorManta, S.en
dc.creatorParmenopoulou, V.en
dc.creatorDimopoulou, A.en
dc.creatorKollatos, N.en
dc.creatorPapasotiriou, I.en
dc.creatorBalzarini, J.en
dc.creatorKomiotis, D.en
dc.date.accessioned2015-11-23T10:34:54Z
dc.date.available2015-11-23T10:34:54Z
dc.date.issued2012
dc.identifier10.1016/j.carres.2012.10.012
dc.identifier.issn0008-6215
dc.identifier.urihttp://hdl.handle.net/11615/29431
dc.description.abstractA new series of 4'-C-cyano and 4'-C-cyano-4'-deoxy pyrimidine pyranonucleosides has been designed and synthesized. Commercially available 1,2,3,4,6-penta-O-acetyl-D-mannopyranose (1) was condensed with silylated 5-fluorouracil, uracil, and thymine, respectively to afford after deacetylation 1-(alpha-D-mannopyranosyl)nucleosides (2a-c). Subjecting 2a-c to the sequence of specific acetalation, selective protection of the primary hydroxyl group and oxidation, the 4'-ketonucleosides 6a-c and 7c were obtained. Reaction of compounds 6a,b, and 7c with sodium cyanide and subsequent deprotection gave the target 1-(4'-C-cyano-alpha-D-mannopyranosyl)nucleosides 12a-c. Deoxygenation at the 4'-position of cyanohydrins 8a,b, and 11c followed by deprotection led to the desired 1-(4'-C-cyano-4'-deoxy-alpha-D-talopyranosyl)nucleosides (15a-c). The newly synthesized compounds were evaluated for their potential antiviral and cytostatic activities in cell culture. (C) 2012 Elsevier Ltd. All rights reserved.en
dc.source.uri<Go to ISI>://WOS:000311359000002
dc.subjectC-Cyano pyranonucleosidesen
dc.subjectStereocontrolled synthesisen
dc.subjectCytotoxicityen
dc.subject5-Fluorouracilen
dc.subjectFLUORO-KETOPYRANOSYL NUCLEOSIDESen
dc.subjectBIOLOGICAL EVALUATIONen
dc.subjectN-4-BENZOYLen
dc.subjectCYTOSINEen
dc.subjectN-6-BENZOYL ADENINEen
dc.subject1,5-ANHYDROHEXITOL NUCLEOSIDESen
dc.subjectEXOMETHYLENE PYRANONUCLEOSIDESen
dc.subjectUNSATURATED EXOMETHYLENEen
dc.subjectANALOGSen
dc.subjectDERIVATIVESen
dc.subjectANTITUMORen
dc.subjectBiochemistry & Molecular Biologyen
dc.subjectChemistry, Applieden
dc.subjectChemistry, Organicen
dc.titleStereocontrolled synthesis of 4 '-C-cyano and 4 '-C-cyano-4 '-deoxy pyrimidine pyranonucleosides as potential chemotherapeutic agentsen
dc.typejournalArticleen


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