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The design, synthesis, and antiviral activity of 4'-azidocytidine analogues against hepatitis C virus replication: the discovery of 4'-azidoarabinocytidine. 2009
David B Smith, and
Genadiy Kalayanov, and
Christian Sund, and
Anna Winqvist, and
Pedro Pinho, and
Tatiana Maltseva, and
Veronique Morisson, and
Vincent Leveque, and
Sonal Rajyaguru, and
Sophie Le Pogam, and
Isabel Najera, and
Kurt Benkestock, and
Xiao-Xiong Zhou, and
Hans Maag, and
Nick Cammack, and
Joseph A Martin, and
Steven Swallow, and
Nils Gunnar Johansson, and
Klaus Klumpp, and
Mark Smith
Roche Palo Alto LLC, Palo Alto, California 94304, USA.
4'-Azidocytidine 3 (R1479) has been previously discovered as a potent and selective inhibitor of HCV replication targeting the RNA-dependent RNA polymerase of hepatitis C virus, NS5B. Here we describe the synthesis and biological evaluation of several derivatives of 4'-azidocytidine by varying the substituents at the ribose 2' and 3'-positions. The most potent compound in this series is 4'-azidoarabinocytidine with an IC(50) of 0.17 microM in the genotype 1b subgenomic replicon system. The structure-activity relationships within this series of nucleoside analogues are discussed.
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