Literature DB >> 26819659

Synthesis and Evaluation of 2,6-Modified Purine 2'-C-Methyl Ribonucleosides as Inhibitors of HCV Replication.

Longhu Zhou1, Hongwang Zhang1, Sijia Tao1, Maryam Ehteshami1, Jong Hyun Cho1, Tamara R McBrayer2, Philip Tharnish2, Tony Whitaker2, Franck Amblard1, Steven J Coats2, Raymond F Schinazi1.   

Abstract

A variety of 2,6-modified purine 2'-C-methylribonucleosides and their phosphoramidate prodrugs were synthesized and evaluated for inhibition of HCV RNA replication in Huh-7 cells and for cytotoxicity in various cell lines. Cellular pharmacology and HCV polymerase incorporation studies on the most potent and selective compound are reported.

Entities:  

Keywords:  HCV; antiviral; nucleoside; phosphoramidate prodrug; purine

Year:  2015        PMID： 26819659      PMCID： PMC4716611          DOI： 10.1021/acsmedchemlett.5b00402

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  18 in total

1.  Ribonucleoside analogue that blocks replication of bovine viral diarrhea and hepatitis C viruses in culture.

Authors:  Lieven J Stuyver; Tony Whitaker; Tamara R McBrayer; Brenda I Hernandez-Santiago; Stefania Lostia; Phillip M Tharnish; Mangala Ramesh; Chung K Chu; Robert Jordan; Junxing Shi; Suguna Rachakonda; Kyoichi A Watanabe; Michael J Otto; Raymond F Schinazi
Journal:  Antimicrob Agents Chemother       Date:  2003-01       Impact factor: 5.191

2.  Adenosine deaminase-like protein 1 (ADAL1): characterization and substrate specificity in the hydrolysis of N(6)- or O(6)-substituted purine or 2-aminopurine nucleoside monophosphates.

Authors:  Eisuke Murakami; Haiying Bao; Ralph T Mosley; Jinfa Du; Michael J Sofia; Phillip A Furman
Journal:  J Med Chem       Date:  2011-07-22       Impact factor: 7.446

3.  N2-amination of guanine to 2-hydrazinohypoxanthine, a novel in vivo nucleic acid modification produced by the hepatocarcinogen 2-nitropropane.

Authors:  R S Sodum; E S Fiala
Journal:  Chem Res Toxicol       Date:  1998-12       Impact factor: 3.739

4.  N6-Cycloalkyl-2-substituted adenosine derivatives as selective, high affinity adenosine A1 receptor agonists.

Authors:  Elfatih Elzein; Rao Kalla; Xiaofen Li; Thao Perry; Tim Marquart; Mark Micklatcher; Yuan Li; Yuzhi Wu; Dewan Zeng; Jeff Zablocki
Journal:  Bioorg Med Chem Lett       Date:  2006-10-11       Impact factor: 2.823

5.  Application of phosphoramidate ProTide technology significantly improves antiviral potency of carbocyclic adenosine derivatives.

Authors:  Christopher McGuigan; Alshaimaa Hassan-Abdallah; Sheila Srinivasan; Yikang Wang; Adam Siddiqui; Susan M Daluge; Kristjan S Gudmundsson; Huiqiang Zhou; Ed W McLean; Jennifer P Peckham; Thimysta C Burnette; Harry Marr; Richard Hazen; Lynn D Condreay; Lance Johnson; Jan Balzarini
Journal:  J Med Chem       Date:  2006-11-30       Impact factor: 7.446

Review 6.  Challenges and successes in developing new therapies for hepatitis C.

Authors:  Raffaele De Francesco; Giovanni Migliaccio
Journal:  Nature       Date:  2005-08-18       Impact factor: 49.962

7.  8-Methylguanosine: a powerful Z-DNA stabilizer.

Authors:  Yan Xu; Reiko Ikeda; Hiroshi Sugiyama
Journal:  J Am Chem Soc       Date:  2003-11-05       Impact factor: 15.419

Review 8.  Nucleoside, nucleotide, and non-nucleoside inhibitors of hepatitis C virus NS5B RNA-dependent RNA-polymerase.

Authors:  Michael J Sofia; Wonsuk Chang; Phillip A Furman; Ralph T Mosley; Bruce S Ross
Journal:  J Med Chem       Date:  2012-01-23       Impact factor: 7.446

9.  Sensitivity of mitochondrial transcription and resistance of RNA polymerase II dependent nuclear transcription to antiviral ribonucleosides.

Authors:  Jamie J Arnold; Suresh D Sharma; Joy Y Feng; Adrian S Ray; Eric D Smidansky; Maria L Kireeva; Aesop Cho; Jason Perry; Jennifer E Vela; Yeojin Park; Yili Xu; Yang Tian; Darius Babusis; Ona Barauskus; Blake R Peterson; Averell Gnatt; Mikhail Kashlev; Weidong Zhong; Craig E Cameron
Journal:  PLoS Pathog       Date:  2012-11-15       Impact factor: 6.823

10.  Structure-activity relationship of purine ribonucleosides for inhibition of hepatitis C virus RNA-dependent RNA polymerase.

Authors:  Anne B Eldrup; Charles R Allerson; C Frank Bennett; Sanjib Bera; Balkrishen Bhat; Neelima Bhat; Michele R Bosserman; Jennifer Brooks; Christine Burlein; Steven S Carroll; P Dan Cook; Krista L Getty; Malcolm MacCoss; Daniel R McMasters; David B Olsen; Thazha P Prakash; Marija Prhavc; Quanlai Song; Joanne E Tomassini; Jie Xia
Journal:  J Med Chem       Date:  2004-04-22       Impact factor: 7.446
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  9 in total

1.  Nucleotide Substrate Specificity of Anti-Hepatitis C Virus Nucleoside Analogs for Human Mitochondrial RNA Polymerase.

Authors:  Maryam Ehteshami; Longhu Zhou; Sheida Amiralaei; Jadd R Shelton; Jong Hyun Cho; Hongwang Zhang; Hao Li; Xiao Lu; Tugba Ozturk; Richard Stanton; Franck Amblard; Tamara R McBrayer; Steven J Coats; Raymond F Schinazi
Journal:  Antimicrob Agents Chemother       Date:  2017-07-25       Impact factor: 5.191

2.  Nucleoside Analogs with Selective Antiviral Activity against Dengue Fever and Japanese Encephalitis Viruses.

Authors:  Keivan Zandi; Leda Bassit; Franck Amblard; Bryan D Cox; Pouya Hassandarvish; Ehsan Moghaddam; Andrew Yueh; Gisele Olinto Libanio Rodrigues; Ingredy Passos; Vivian V Costa; Sazaly AbuBakar; Longhu Zhou; James Kohler; Mauro M Teixeira; Raymond F Schinazi
Journal:  Antimicrob Agents Chemother       Date:  2019-06-24       Impact factor: 5.191

3.  In silico design of a novel nucleotide antiviral agent by free energy perturbation.

Authors:  Dharmeshkumar Patel; Bryan D Cox; Mahesh Kasthuri; Seema Mengshetti; Leda Bassit; Kiran Verma; Olivia Ollinger-Russell; Franck Amblard; Raymond F Schinazi
Journal:  Chem Biol Drug Des       Date:  2022-04-07       Impact factor: 2.873

4.  Synthesis of 7-trifluoromethyl-7-deazapurine ribonucleoside analogs and their monophosphate prodrugs.

Authors:  Jong Hyun Cho; Leda C Bassit; Franck Amblard; Raymond F Schinazi
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2019-10-07       Impact factor: 1.381

5.  Exploring the purine core of 3'-C-ethynyladenosine (EAdo) in search of novel nucleoside therapeutics.

Authors:  Fabian Hulpia; Jan Balzarini; Dominique Schols; Graciela Andrei; Robert Snoeck; Serge Van Calenbergh
Journal:  Bioorg Med Chem Lett       Date:  2016-03-03       Impact factor: 2.823

6.  Synthesis of a 3'-C-ethynyl-β-d-ribofuranose purine nucleoside library: Discovery of C7-deazapurine analogs as potent antiproliferative nucleosides.

Authors:  Fabian Hulpia; Sam Noppen; Dominique Schols; Graciela Andrei; Robert Snoeck; Sandra Liekens; Peter Vervaeke; Serge Van Calenbergh
Journal:  Eur J Med Chem       Date:  2018-07-29       Impact factor: 6.514

7.  DFT, Monte Carlo and molecular dynamics simulations for the prediction of corrosion inhibition efficiency of novel pyrazolylnucleosides on Cu(111) surface in acidic media.

Authors:  Rachid Oukhrib; Youness Abdellaoui; Avni Berisha; Hicham Abou Oualid; Jeton Halili; Kaltrina Jusufi; Mustapha Ait El Had; Hassan Bourzi; Souad El Issami; Fatmah Ali Asmary; Virinder S Parmar; Christophe Len
Journal:  Sci Rep       Date:  2021-02-12       Impact factor: 4.379

8.  Diastereoselective Synthesis of 2'-Dihalopyrimidine Ribonucleoside Inhibitors of Hepatitis C Virus Replication.

Authors:  Longhu Zhou; Hongwang Zhang; Chengwei Li; Coralie De Schutter; Ozkan Sari; Seema Mengshetti; Shaoman Zhou; Mahesh Kasthuri; Steven J Coats; Raymond F Schinazi; Franck Amblard
Journal:  ACS Omega       Date:  2021-12-22

9.  Synthetic, Structural, and Anticancer Activity Evaluation Studies on Novel Pyrazolylnucleosides.

Authors:  Yogesh Yadav; Deepti Sharma; Kumar Kaushik; Vineet Kumar; Amitabh Jha; Ashok K Prasad; Christophe Len; Sanjay V Malhotra; Jesper Wengel; Virinder S Parmar
Journal:  Molecules       Date:  2019-10-30       Impact factor: 4.411
  9 in total

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