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



: Leisvuori A, Ahmed Z, Ora M, Beigelman L, Blatt L, Lonnberg H

Publisher: WILEY-V C H VERLAG GMBH

: 2012

: Helvetica Chimica Acta

: HELVETICA CHIMICA ACTA

: HELV CHIM ACTA

: 9

: 95

: 9

: 1512

: 1520

: 9

: 0018-019X

DOI: https://doi.org/10.1002/hlca.201200099

: 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.

Last updated on 2024-26-11 at 15:09