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Design, Synthesis, and Antiviral Activity of 2'-deoxy-2'-fluoro-2'-C-methylcytidine, a Potent Inhibitor of Hepatitis C Virus Replication

Design, Synthesis, and Antiviral Activity of 2'-deoxy-2'-fluoro-2'-C-methylcytidine, a Potent Inhibitor of Hepatitis C Virus Replication

Jeremy L Clark, Laurent Hollecker, J Christian Mason, Lieven J Stuyver, Phillip M Tharnish, Stefania Lostia, Tamara R McBrayer, Raymond F Schinazi, Kyoichi A Watanabe, Michael J Otto, Phillip A Furman, etc.

J Med Chem. 2005 Aug 25;48(17):5504-8.

PMID: 16107149

Abstract:

The pyrimidine nucleoside beta-d-2'-deoxy-2'-fluoro-2'-C-methylcytidine (1) was designed as a hepatitis C virus RNA-dependent RNA polymerase (HCV RdRp) inhibitor. The title compound was obtained by a DAST fluorination of N(4)-benzoyl-1-(2-methyl-3,5-di-O-benzoyl-beta-d-arabinofuranosyl]cytosine to provide N(4)-benzoyl-1-[2-fluoro-2-methyl-3,5-di-O-benzoyl-beta-d-ribofuranosyl]cytosine. The protected 2'-C-methylcytidine was obtained as a byproduct from the DAST fluorination and allowed for the preparation of two biologically active compounds from a common precursor. Compound 1 and 2'-C-methylcytidine were assayed in a subgenomic HCV replicon assay system and found to be potent and selective inhibitors of HCV replication. Compound 1 shows increased inhibitory activity in the HCV replicon assay compared to 2'-C-methylcytidine and low cellular toxicity.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP20724736	2'-C-Methylcytidine		20724-73-6	Price

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