Synthesis of N3,5‘-Cyclo-4-(β-<scp>d</scp>-ribofuranosyl)-vic-triazolo[4,5-b]pyridin-5-one, a Novel Compound with Anti-Hepatitis C Virus Activity

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

doi:10.1021/jm0401210

Cited by 24 publications

(9 citation statements)

References 11 publications

(32 reference statements)

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“…This would indicate that the anti-HCV activity is associated with the cytostatic affect of these compounds. This relationship was previously observed with N 3 ,5‘-cyclo-4-(β- d -ribofuranosyl)- vic -triazolo[4,5]pyridin-5-one …”

Section: Resultssupporting

confidence: 81%

Cytostatic 6-Arylpurine Nucleosides. 6. SAR in Anti-HCV and Cytostatic Activity of Extended Series of 6-Hetarylpurine Ribonucleosides

et al. 2005

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Significant anti-HCV activity of 6-hetarylpurine ribonucleosides has been discovered and is reported here for the first time and compared with cytostatic effect. An extended series of 6-hetarylpurine nucleosides has been prepared by heterocyclizations in position 6 of purine nucleosides or by cross-couplings of 6-chloropurine nucleosides with hetarylboronic acids, -stannanes, or -zinc halides. The most anti-HCV active were purine ribonucleosides bearing pyrrol-3-yl or 2-furyl groups exerting EC(90) = 0.14 and 0.4 microM, respectively.

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Section: Resultssupporting

confidence: 81%

Cytostatic 6-Arylpurine Nucleosides. 6. SAR in Anti-HCV and Cytostatic Activity of Extended Series of 6-Hetarylpurine Ribonucleosides

et al. 2005

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“…(Riley et al, 1990;Wang et al, 2004). Some of these important drugs -bredenin, pyrazofurin, ribavirin and their analogues -have immunosuppressive, antitumour and antiviral activities.…”

mentioning

confidence: 99%

Synthesis and Antiviral Activities of 1,2,3-triazole Functionalized Thymidines: 1,3-dipolar Cycloaddition for Efficient Regioselective Diversity Generation

Zhou

Amer

Korn

et al. 2005

Antivir Chem Chemother

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Efficient regioselective synthesis of nucleoside conjugates was achieved by cycloaddition reaction of azides and alkynes using sodium ascorbate/ CuSO4 system as a catalyst. These 16 novel thymidine analogues were obtained in excellent yields (75-100%), employing mild reaction conditions with a broad scope of structural modification. For the compounds tested, no specific antiviral effects could be witnessed against a broad range of viruses.

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“…Base modified ribonucleosides such as triazolopyridine 14a [66,67] or 6-heteroarylpurine derivatives 14b [68] are active in cells, but also cytotoxic. Simpler modifications of the 6-position such as in 15a,b showed low micromolar activity in the replicon assay [69].…”

Section: '-Modified Nucleoside Inhibitorsmentioning

confidence: 99%

Recent Progress in the Development of Inhibitors of the Hepatitis C Virus RNA-Dependent RNA Polymerase

Koch¹,

Narjes

2007

CTMC

105

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The global prevalence of hepatitis C virus (HCV) infection and the serious consequences associated with the chronic state of the disease have become a worldwide health problem. A combination therapy comprising Interferon-alpha and Ribavirin represents the current standard treatment for chronic HCV infection, although it has demonstrated limited success and causes serious side effects. Promising alternative approaches toward the control of HCV infection include the development of small molecule inhibitors of viral enzymes interfering with the essential steps in the life cycle of the virus. In this review we will focus on inhibitors of the HCV-encoded NS5B RNA-dependent RNA polymerase (NS5B RdRp) which is essential for viral replication and has been recognized as a prime target for therapeutic intervention.

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Synthesis of N³,5‘-Cyclo-4-(β-d-ribofuranosyl)-vic-triazolo[4,5-b]pyridin-5-one, a Novel Compound with Anti-Hepatitis C Virus Activity

Abstract: A novel anti-hepatitis C virus (HCV) agent, N(3),5'-cyclo-4-(beta-D-ribofuranosyl)-vic-triazolo[4,5-b]pyridinin-5-one, was identified, and the structure was confirmed by chemical synthesis from 2-hydroxy-5-nitropyridine.

Cited by 24 publications

References 11 publications

Cytostatic 6-Arylpurine Nucleosides. 6. SAR in Anti-HCV and Cytostatic Activity of Extended Series of 6-Hetarylpurine Ribonucleosides

Cytostatic 6-Arylpurine Nucleosides. 6. SAR in Anti-HCV and Cytostatic Activity of Extended Series of 6-Hetarylpurine Ribonucleosides

Synthesis and Antiviral Activities of 1,2,3-triazole Functionalized Thymidines: 1,3-dipolar Cycloaddition for Efficient Regioselective Diversity Generation

Recent Progress in the Development of Inhibitors of the Hepatitis C Virus RNA-Dependent RNA Polymerase

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Synthesis of N3,5‘-Cyclo-4-(β-d-ribofuranosyl)-vic-triazolo[4,5-b]pyridin-5-one, a Novel Compound with Anti-Hepatitis C Virus Activity

Abstract: A novel anti-hepatitis C virus (HCV) agent, N(3),5'-cyclo-4-(beta-D-ribofuranosyl)-vic-triazolo[4,5-b]pyridinin-5-one, was identified, and the structure was confirmed by chemical synthesis from 2-hydroxy-5-nitropyridine.

Cited by 24 publications

References 11 publications

Cytostatic 6-Arylpurine Nucleosides. 6. SAR in Anti-HCV and Cytostatic Activity of Extended Series of 6-Hetarylpurine Ribonucleosides

Cytostatic 6-Arylpurine Nucleosides. 6. SAR in Anti-HCV and Cytostatic Activity of Extended Series of 6-Hetarylpurine Ribonucleosides

Synthesis and Antiviral Activities of 1,2,3-triazole Functionalized Thymidines: 1,3-dipolar Cycloaddition for Efficient Regioselective Diversity Generation

Recent Progress in the Development of Inhibitors of the Hepatitis C Virus RNA-Dependent RNA Polymerase

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Synthesis of N³,5‘-Cyclo-4-(β-d-ribofuranosyl)-vic-triazolo[4,5-b]pyridin-5-one, a Novel Compound with Anti-Hepatitis C Virus Activity