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9-(2',3'-Dideoxy-2',3'-difluoro-β-D-arabinofuranosyl)adenine (20), 2-chloro-9-(2',3'-dideoxy-2,3-difluoro-β-D-arabinofuranosyl)adenine (22), as well as their respective α-anomers 21 and 23, were synthesized by the nucleobase anion glycosylation of intermediate 5-O-benzoyl-2,3-dideoxy-2,3-difluoro-α-D-arabinofuranosyl bromide (13) starting from methyl 5-O-benzyl-3-deoxy-3-fluoro-α-D-ribofuranoside (3) and methyl 5-O-benzoyl-α-D-xylofuranoside (10). These compounds were evaluated as potential inhibitors of HIV-1 and hepatitis C virus in human PBM and Huh-7 Replicon cells, respectively. The adenosine analog 20 demonstrated potent activity against HIV-1 in primary human lymphocytes with no apparent cytotoxicity. Conformation of pentofuranose ring of nucleoside 20 in solution was studied by PSEUROT calculations. [ABSTRACT FROM AUTHOR]

We recently discovered a novel compound, identified as N 3 ,5′-cyclo-4-(β-d-ribofuranosyl)- vic -triazolo[4,5- b ]pyridinin-5-one, with anti-hepatitis C virus (HCV) activity in vitro. The structure was confirmed by chemical synthesis from 2-hydroxy-5-nitropyridine. It showed anti-HCV activity with EC 50 =19.7 µM in replicon cells. Its 3′-deoxy sugar analogue was also synthesized, but was inactive against HCV in vitro. [ABSTRACT FROM AUTHOR]