Literature DB >> 22993455

Efficient synthesis of nucleoside aryloxy phosphoramidate prodrugs utilizing benzyloxycarbonyl protection.

Jong Hyun Cho1, Franck Amblard, Steven J Coats, Raymond F Schinazi.   

Abstract

An efficient method for the synthesis of nucleoside phosphoramidates prodrugs (6a-f) has been developed that employs a simple protection/deprotection sequence of the nucleoside with benzyloxycarbonyl (Cbz). The coupling reaction of Cbz-protected derivatives (5a-f) with phenyl-(ethoxy-L-alaninyl)-phosphorochloridate (7), followed by Cbz group removal by hydrogenolysis provided the phenyl phosphoramidate ProTides (6a-f) in excellent overall yields.

Entities:  

Year:  2011        PMID： 22993455      PMCID： PMC3444294          DOI： 10.1016/j.tet.2011.05.046

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  19 in total

Review 1.  Prodrugs of biologically active phosphate esters.

Authors:  Carsten Schultz
Journal:  Bioorg Med Chem       Date:  2003-03-20       Impact factor: 3.641

2.  Phosphoramidate ProTides of 2'-C-methylguanosine as highly potent inhibitors of hepatitis C virus. Study of their in vitro and in vivo properties.

Authors:  Christopher McGuigan; Arnaud Gilles; Karolina Madela; Mohamed Aljarah; Sabrina Holl; Sarah Jones; John Vernachio; Jeff Hutchins; Brenda Ames; K Dawn Bryant; Elena Gorovits; Babita Ganguly; Damound Hunley; Andrea Hall; Alexander Kolykhalov; Yule Liu; Jerry Muhammad; Nicholas Raja; Robin Walters; Jin Wang; Stanley Chamberlain; Geoffrey Henson
Journal:  J Med Chem       Date:  2010-07-08       Impact factor: 7.446

Review 3.  Advances in nucleoside monophosphate prodrugs as anti-HCV agents.

Authors:  Drew R Bobeck; Raymond F Schinazi; Steven J Coats
Journal:  Antivir Ther       Date:  2010

4.  Anti-hepatitis C virus activity of novel beta-d-2'-C-methyl-4'-azido pyrimidine nucleoside phosphoramidate prodrugs.

Authors:  Ramu Rondla; Steven J Coats; Tamara R McBrayer; Jason Grier; Melissa Johns; Phillip M Tharnish; Tony Whitaker; Longhu Zhou; Raymond F Schinazi
Journal:  Antivir Chem Chemother       Date:  2009-10-19

5.  The presence of substituents on the aryl moiety of the aryl phosphoramidate derivative of d4T enhances anti-HIV efficacy in cell culture: A structure-activity relationship.

Authors:  A Q Siddiqui; C Ballatore; C McGuigan; E De Clercq; J Balzarini
Journal:  J Med Chem       Date:  1999-02-11       Impact factor: 7.446

6.  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

7.  First example of phosphoramidate approach applied to a 4'-substituted purine nucleoside (4'-azidoadenosine): conversion of an inactive nucleoside to a submicromolar compound versus hepatitis C virus.

Authors:  Plinio Perrone; Felice Daverio; Rocco Valente; Sonal Rajyaguru; Joseph A Martin; Vincent Lévêque; Sophie Le Pogam; Isabel Najera; Klaus Klumpp; David B Smith; Christopher McGuigan
Journal:  J Med Chem       Date:  2007-10-03       Impact factor: 7.446

8.  Application of the phosphoramidate ProTide approach to 4'-azidouridine confers sub-micromolar potency versus hepatitis C virus on an inactive nucleoside.

Authors:  Plinio Perrone; Giovanna M Luoni; Mary Rose Kelleher; Felice Daverio; Annette Angell; Sinead Mulready; Costantino Congiatu; Sonal Rajyaguru; Joseph A Martin; Vincent Levêque; Sophie Le Pogam; Isabel Najera; Klaus Klumpp; David B Smith; Christopher McGuigan
Journal:  J Med Chem       Date:  2007-03-17       Impact factor: 7.446

9.  The phosphoramidate ProTide approach greatly enhances the activity of beta-2'-C-methylguanosine against hepatitis C virus.

Authors:  Christopher McGuigan; Plinio Perrone; Karolina Madela; Johan Neyts
Journal:  Bioorg Med Chem Lett       Date:  2009-06-10       Impact factor: 2.823

10.  Application of the phosphoramidate ProTide approach to the antiviral drug ribavirin.

Authors:  Marco Derudas; Andrea Brancale; Lieve Naesens; Johan Neyts; Jan Balzarini; Christopher McGuigan
Journal:  Bioorg Med Chem       Date:  2010-02-15       Impact factor: 3.641
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  6 in total

1.  Synthesis and antiviral evaluation of 2-amino-6-carbamoylpurine dioxolane nucleoside derivatives and their phosphoramidates prodrugs.

Authors:  Jong Hyun Cho; Lavanya Bondana; Mervi A Detorio; Cathy Montero; Leda C Bassit; Franck Amblard; Steven J Coats; Raymond F Schinazi
Journal:  Bioorg Med Chem       Date:  2014-10-13       Impact factor: 3.641

Review 2.  Synthesis of nucleoside phosphate and phosphonate prodrugs.

Authors:  Ugo Pradere; Ethel C Garnier-Amblard; Steven J Coats; Franck Amblard; Raymond F Schinazi
Journal:  Chem Rev       Date:  2014-08-21       Impact factor: 60.622

3.  Efficient synthesis of exo-N-carbamoyl nucleosides: application to the synthesis of phosphoramidate prodrugs.

Authors:  Jong Hyun Cho; Steven J Coats; Raymond F Schinazi
Journal:  Org Lett       Date:  2012-05-03       Impact factor: 6.005

Review 4.  Phosphoramidates and phosphonamidates (ProTides) with antiviral activity.

Authors:  Magdalena Slusarczyk; Michaela Serpi; Fabrizio Pertusati
Journal:  Antivir Chem Chemother       Date:  2018 Jan-Dec

5.  Synthesis and biological evaluation of phosphoramidate prodrugs of two analogues of 2-deoxy-d-ribose-1-phosphate directed to the discovery of two carbasugars as new potential anti-HIV leads.

Authors:  Nadège Hamon; Magdalena Slusarczyk; Michaela Serpi; Jan Balzarini; Christopher McGuigan
Journal:  Bioorg Med Chem       Date:  2014-12-25       Impact factor: 3.641

6.  Synthesis and biological evaluation of prodrugs of 2-fluoro-2-deoxyribose-1-phosphate and 2,2-difluoro-2-deoxyribose-1-phosphate.

Authors:  Nadege Hamon; Maurizio Quintiliani; Jan Balzarini; Christopher McGuigan
Journal:  Bioorg Med Chem Lett       Date:  2013-03-14       Impact factor: 2.823
  6 in total

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