Literature DB >> 16368235

Synthesis and antiviral activity of 2'-deoxy-2'-fluoro-2'-C-methyl purine nucleosides as inhibitors of hepatitis C virus RNA replication.

Jeremy L Clark1, J Christian Mason, Laurent Hollecker, Lieven J Stuyver, Phillip M Tharnish, Tamara R McBrayer, Michael J Otto, Phillip A Furman, Raymond F Schinazi, Kyoichi A Watanabe.   

Abstract

A series of purine nucleosides containing the 2'-deoxy-2'-fluoro-2'-C-methylribofuranosyl moiety were synthesized and evaluated as potential inhibitors of the hepatitis C virus in vitro. Of the nucleosides that were synthesized, only those possessing a 2-amino group on the purine base reduced the levels of HCV RNA in a subgenomic replicon assay.

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Year:  2005        PMID： 16368235     DOI： 10.1016/j.bmcl.2005.12.002

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  13 in total

1.  Discovery of PSI-353661, a Novel Purine Nucleotide Prodrug for the Treatment of HCV Infection.

Authors:  Wonsuk Chang; Donghui Bao; Byoung-Kwon Chun; Devan Naduthambi; Dhanapalan Nagarathnam; Suguna Rachakonda; P Ganapati Reddy; Bruce S Ross; Hai-Ren Zhang; Shalini Bansal; Christine L Espiritu; Meg Keilman; Angela M Lam; Congrong Niu; Holly Micolochick Steuer; Phillip A Furman; Michael J Otto; Michael J Sofia
Journal:  ACS Med Chem Lett       Date:  2010-12-17       Impact factor: 4.345

2.  Metabolic activation of the anti-hepatitis C virus nucleotide prodrug PSI-352938.

Authors:  Congrong Niu; Tatiana Tolstykh; Haiying Bao; Yeojin Park; Darius Babusis; Angela M Lam; Shalini Bansal; Jinfa Du; Wonsuk Chang; P Ganapati Reddy; Hai-Ren Zhang; Joseph Woolley; Li-Quan Wang; Piyun B Chao; Adrian S Ray; Michael J Otto; Michael J Sofia; Phillip A Furman; Eisuke Murakami
Journal:  Antimicrob Agents Chemother       Date:  2012-04-23       Impact factor: 5.191

3.  Activity and the metabolic activation pathway of the potent and selective hepatitis C virus pronucleotide inhibitor PSI-353661.

Authors:  Phillip A Furman; Eisuke Murakami; Congrong Niu; Angela M Lam; Christine Espiritu; Shalini Bansal; Haiying Bao; Tatiana Tolstykh; Holly Micolochick Steuer; Meg Keilman; Veronique Zennou; Nigel Bourne; Ronald L Veselenak; Wonsuk Chang; Bruce S Ross; Jinfa Du; Michael J Otto; Michael J Sofia
Journal:  Antiviral Res       Date:  2011-05-12       Impact factor: 5.970

4.  High-Throughput Screening Identifies Inhibitors for Parvovirus B19 Infection of Human Erythroid Progenitors.

Authors:  Kang Ning; Anuradha Roy; Fang Cheng; Peng Xu; Steve Kleiboeker; Carlos R Escalante; Jingxin Wang; Jianming Qiu
Journal:  J Virol       Date:  2021-10-20       Impact factor: 6.549

5.  The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.

Authors:  Eisuke Murakami; Congrong Niu; Haiying Bao; Holly M Micolochick Steuer; Tony Whitaker; Tammy Nachman; Michael A Sofia; Peiyuan Wang; Michael J Otto; Phillip A Furman
Journal:  Antimicrob Agents Chemother       Date:  2007-11-12       Impact factor: 5.191

6.  Synthesis of 5'-methylene-phosphonate furanonucleoside prodrugs: application to D-2'-deoxy-2'-α-fluoro-2'-β-C-methyl nucleosides.

Authors:  Ugo Pradere; Franck Amblard; Steven J Coats; Raymond F Schinazi
Journal:  Org Lett       Date:  2012-08-23       Impact factor: 6.005

7.  Fluorinated Nucleosides: Synthesis and Biological Implication.

Authors:  Peng Liu; Ashoke Sharon; Chung K Chu
Journal:  J Fluor Chem       Date:  2008-09       Impact factor: 2.050

8.  PSI-7851, a pronucleotide of beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine monophosphate, is a potent and pan-genotype inhibitor of hepatitis C virus replication.

Authors:  Angela M Lam; Eisuke Murakami; Christine Espiritu; Holly M Micolochick Steuer; Congrong Niu; Meg Keilman; Haiying Bao; Veronique Zennou; Nigel Bourne; Justin G Julander; John D Morrey; Donald F Smee; David N Frick; Julie A Heck; Peiyuan Wang; Dhanapalan Nagarathnam; Bruce S Ross; Michael J Sofia; Michael J Otto; Phillip A Furman
Journal:  Antimicrob Agents Chemother       Date:  2010-06-01       Impact factor: 5.191

9.  Discovery of a Series of 2'-α-Fluoro,2'-β-bromo-ribonucleosides and Their Phosphoramidate Prodrugs as Potent Pan-Genotypic Inhibitors of Hepatitis C Virus.

Authors:  Seema Mengshetti; Longhu Zhou; Ozkan Sari; Coralie De Schutter; Hongwang Zhang; Jong Hyun Cho; Sijia Tao; Leda C Bassit; Kiran Verma; Robert A Domaoal; Maryam Ehteshami; Yong Jiang; Reuben Ovadia; Mahesh Kasthuri; Olivia Ollinger Russell; Tamara McBrayer; Tony Whitaker; Judy Pattassery; Maria Luz Pascual; Lothar Uher; Biing Y Lin; Sam Lee; Franck Amblard; Steven J Coats; Raymond F Schinazi
Journal:  J Med Chem       Date:  2019-02-07       Impact factor: 7.446

10.  Debio 025, a cyclophilin binding molecule, is highly efficient in clearing hepatitis C virus (HCV) replicon-containing cells when used alone or in combination with specifically targeted antiviral therapy for HCV (STAT-C) inhibitors.

Authors:  Lotte Coelmont; Suzanne Kaptein; Jan Paeshuyse; Inge Vliegen; Jean-Maurice Dumont; Grégoire Vuagniaux; Johan Neyts
Journal:  Antimicrob Agents Chemother       Date:  2008-12-22       Impact factor: 5.191
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