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6-Hydrazinopurine 2'-methyl ribonucleosides and their 5'-monophosphate prodrugs as potent hepatitis C virus inhibitors. 2007
Esmir Gunic, and
Suetying Chow, and
Frank Rong, and
Kanda Ramasamy, and
Anneke Raney, and
David Yunzhi Li, and
Jingfan Huang, and
Robert K Hamatake, and
Zhi Hong, and
Jean-Luc Girardet
Valeant Research and Development, 3300 Hyland Avenue, Costa Mesa, CA 92626, USA.
A series of 6-hydrazinopurine 2'-methyl ribonucleosides was synthesized and tested for its inhibitory activity against the hepatitis C virus (HCV). The lack of antiviral activity of these nucleosides was associated with a poor affinity for adenosine kinase, which prompted us to synthesize several of their 5'-monophosphate prodrugs. Some of these prodrugs exhibited more than 1000-fold improvement in anti-HCV activity when compared to their parent nucleosides (EC(50) of 24 nM vs 92 microM for the parent).
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