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An efficient synthesis of 3-fluoro-5-thio-xylofuranosyl nucleosides of thymine, uracil, and 5-fluorouracil as potential antitumor or/and antiviral agents

dc.creatorTsoukala, E.en
dc.creatorAgelis, G.en
dc.creatorDolinsek, J.en
dc.creatorBotic, T.en
dc.creatorCencic, A.en
dc.creatorKomiotis, D.en
dc.date.accessioned2015-11-23T10:52:24Z
dc.date.available2015-11-23T10:52:24Z
dc.date.issued2007
dc.identifier10.1016/j.bmc.2007.02.031
dc.identifier.issn0968-0896
dc.identifier.urihttp://hdl.handle.net/11615/34073
dc.description.abstract1,2:5,6-Di-O-isopropylidene-alpha-D-glucofuranose by the sequence of mild oxidation, reduction, fluorination, periodate oxidation, borohydride reduction, and sulfonylation gave 3-deoxy-3-fluoro-1,2-O-isopropylidene-5-O-p-toluenesulfonyl-alpha-D-xylofuranose (5). Tosylate 5 was converted to thioacetate derivative 6, which after acetolysis gave 1,2-di-O-acetyl-5-S-acetyl-3-deoxy-3-fluoro-5-thio-beta-xylofuranose (7). Condensation of 7 with silylated thymine, uracil, and 5-fluorouracil afforded nucleosides 1-(5-S-acetyl-3-deoxy-3-fluoro-5-thio-beta-D-xylofuranosyl) thymine (8), 1-(5-S-acetyl-3-deoxy-3-fluoro-5-thio-beta-D-xylofuranosyl) uracil (9), and 1-(5-S-acetyl-3-deoxy-3-fluoro-5-thio-beta-D-xylofuranosyl) 5-fluorouracil (10). Compounds 8, 9, and 10 are biologically active against rotavirus infection and the growth of tumor cells. (c) 2007 Elsevier Ltd. All rights reserved.en
dc.source.uri<Go to ISI>://WOS:000246002800016
dc.subject3-deoxy-3-fluoro-5-thio-xylofuranoseen
dc.subjectnucleosideen
dc.subjectthymineen
dc.subjecturacilen
dc.subject5-fluorouracilen
dc.subjectantiviralen
dc.subjectantitumor agenten
dc.subjectTHYMIDINE KINASE ISOZYMESen
dc.subject2',3'-DIDEOXYNUCLEOSIDE ANALOGSen
dc.subjectENZYME-INHIBITORSen
dc.subjectCELLSen
dc.subjectSUBSTITUENTSen
dc.subjectMITOCHONDRIAen
dc.subjectAFFINITYen
dc.subjectSERIESen
dc.subjectMOUSEen
dc.subjectBiochemistry & Molecular Biologyen
dc.subjectChemistry, Medicinalen
dc.subjectChemistry,en
dc.subjectOrganicen
dc.titleAn efficient synthesis of 3-fluoro-5-thio-xylofuranosyl nucleosides of thymine, uracil, and 5-fluorouracil as potential antitumor or/and antiviral agentsen
dc.typejournalArticleen


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