A1 Refereed original research article in a scientific journal
Synthesis of 3',5'-Cyclic Phosphate and Thiophosphate Esters of 2'-C-Methyl Ribonucleosides
Authors: Leisvuori A, Ahmed Z, Ora M, Beigelman L, Blatt L, Lonnberg H
Publisher: WILEY-V C H VERLAG GMBH
Publication year: 2012
Journal: Helvetica Chimica Acta
Journal name in source: HELVETICA CHIMICA ACTA
Journal acronym: HELV CHIM ACTA
Number in series: 9
Volume: 95
Issue: 9
First page : 1512
Last page: 1520
Number of pages: 9
ISSN: 0018-019X
DOI: https://doi.org/10.1002/hlca.201200099
Self-archived copy’s web address: https://research.utu.fi/converis/portal/detail/Publication/1441658
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.
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