Synthesis of N3,5′-cyclo-4-(β-D-ribofuranosyl)-vic- triazolo[4,5-b]pyridin-5-one and its 3′-deoxysugar analogue as potential anti-hepatitis C virus agents

Peiyuan Wang; Laurent Hollecker; Krzysztof W. Pankiewicz; Steven E. Patterson; Tony Whitaker; Tamara R. McBrayer; Phillip M. Tharnish; Lieven J. Stuyver; Raymond F. Schinazi; Michael J. Otto; Kyoichi A. Watanabe

doi:10.1081/NCN-200059314

Synthesis of N³,5′-cyclo-4-(β-D-ribofuranosyl)-vic- triazolo[4,5-b]pyridin-5-one and its 3′-deoxysugar analogue as potential anti-hepatitis C virus agents

Peiyuan Wang
, Laurent Hollecker
, Krzysztof W. Pankiewicz
, Steven E. Patterson
, Tony Whitaker
, Tamara R. McBrayer
, Phillip M. Tharnish
, Lieven J. Stuyver
, Raymond F. Schinazi
, Michael J. Otto
, Kyoichi A. Watanabe

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

Abstract

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 EC50 = 19.7 μM in replicon cells. Its 3′-deoxy sugar analogue was also synthesized, but was inactive against HCV in vitro.

Original language	English (US)
Pages (from-to)	957-960
Number of pages	4
Journal	Nucleosides, Nucleotides and Nucleic Acids
Volume	24
Issue number	5-7
DOIs	https://doi.org/10.1081/NCN-200059314
State	Published - 2005
Externally published	Yes

Bibliographical note

Funding Information:
Supported in parts by NIH grants 1R43 AI-52868 (biology) and 1 R43 AI-056720 (chemistry). We would like to acknowledge the contribution of D. L. Barnard, J. D. Morrey, and D. F. Smee at the Institute for Antiviral Research at Utah State University for their testing of RNA viruses under NIH Contract No. N01-A1-85348. Dr. Schinazi is a founder and consultant of Pharmasset, Inc. His laboratory did not receive any funding from Pharmasset, Inc.

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being
SDG 7 Affordable and Clean Energy

Publisher link

10.1081/NCN-200059314

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Cite this

Wang, P., Hollecker, L., Pankiewicz, K. W., Patterson, S. E., Whitaker, T., McBrayer, T. R., Tharnish, P. M., Stuyver, L. J., Schinazi, R. F., Otto, M. J., & Watanabe, K. A. (2005). Synthesis of N³,5′-cyclo-4-(β-D-ribofuranosyl)-vic- triazolo[4,5-b]pyridin-5-one and its 3′-deoxysugar analogue as potential anti-hepatitis C virus agents. Nucleosides, Nucleotides and Nucleic Acids, 24(5-7), 957-960. https://doi.org/10.1081/NCN-200059314

Synthesis of N³,5′-cyclo-4-(β-D-ribofuranosyl)-vic- triazolo[4,5-b]pyridin-5-one and its 3′-deoxysugar analogue as potential anti-hepatitis C virus agents. / Wang, Peiyuan; Hollecker, Laurent; Pankiewicz, Krzysztof W. et al.
In: Nucleosides, Nucleotides and Nucleic Acids, Vol. 24, No. 5-7, 2005, p. 957-960.

Research output: Contribution to journal › Article › peer-review

Wang, P, Hollecker, L, Pankiewicz, KW, Patterson, SE, Whitaker, T, McBrayer, TR, Tharnish, PM, Stuyver, LJ, Schinazi, RF, Otto, MJ & Watanabe, KA 2005, 'Synthesis of N³,5′-cyclo-4-(β-D-ribofuranosyl)-vic- triazolo[4,5-b]pyridin-5-one and its 3′-deoxysugar analogue as potential anti-hepatitis C virus agents', Nucleosides, Nucleotides and Nucleic Acids, vol. 24, no. 5-7, pp. 957-960. https://doi.org/10.1081/NCN-200059314

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abstract = "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 EC50 = 19.7 μM in replicon cells. Its 3′-deoxy sugar analogue was also synthesized, but was inactive against HCV in vitro.",

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note = "Funding Information: Supported in parts by NIH grants 1R43 AI-52868 (biology) and 1 R43 AI-056720 (chemistry). We would like to acknowledge the contribution of D. L. Barnard, J. D. Morrey, and D. F. Smee at the Institute for Antiviral Research at Utah State University for their testing of RNA viruses under NIH Contract No. N01-A1-85348. Dr. Schinazi is a founder and consultant of Pharmasset, Inc. His laboratory did not receive any funding from Pharmasset, Inc.",

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