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Synthesis of 3',5'-Cyclic Phosphate and Thiophosphate Esters of 2'-C-Methyl Ribonucleosides

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Details

Original languageEnglish
Pages (from-to)1512-1520
Number of pages9
JournalHELVETICA CHIMICA ACTA
Volume95
Issue number9
DOIs
Publication statusPublished - Sep 2012
Publication typeA1 Journal article-refereed

Abstract

2'-C-Methylnucleosides are known to exhibit antiviral activity against Hepatitis C virus. Since the inhibitory activity depends on their intracellular conversion to 5'-triphosphates, dosing as appropriately protected 5'-phosphates or 5'-phosphorothioates appears attractive. For this purpose, four potential pro-drugs of 2'-C-methylguanosine, i.e., 3',5'-cyclic phosphorothioate of 2'-C-methylguanosine and 2'-C,O6-dimethylguanosine, 1 and 2, respectively, the S-[(pivaloyloxy)methyl] ester of 2'-C,O6-dimethylguanosine 3',5'-cyclic phosphorothioate and the O-methyl ester of 2'-C,O6-dimethylguanosine 3',5'-cyclic phosphate, 3 and 4, respectively, have been prepared.

Keywords

  • Nucleosides, Prodrugs, Phosphorothioate, HEPATITIS-C-VIRUS, MONOPHOSPHATE PRODRUGS