Literature DB >> 19505826

The application of phosphoramidate ProTide technology to the potent anti-HCV compound 4'-azidocytidine (R1479).

Christopher McGuigan1, Mary Rose Kelleher, Plinio Perrone, Sinead Mulready, Giovanna Luoni, Felice Daverio, Sonal Rajyaguru, Sophie Le Pogam, Isabel Najera, Joseph A Martin, Klaus Klumpp, David B Smith.   

Abstract

We report the design, synthesis and evaluation of a family of ca 50 phosphoramidate ProTides of the potent anti-HCV compound 4'-azidocytidine (R1479), with variation on the ester, amino acid and aryl moiety of the ProTide. Sub-muM inhibitors of HCV emerge. The compounds are all non-cytotoxic in the replicon assay. We herein report detailed SARs for each of the regions of the ProTide.

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Year:  2009        PMID: 19505826     DOI: 10.1016/j.bmcl.2009.05.099

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


  9 in total

1.  Thiophene-expanded guanosine analogues of Gemcitabine.

Authors:  Zhe Chen; Therese C Ku; Katherine L Seley-Radtke
Journal:  Bioorg Med Chem Lett       Date:  2015-07-30       Impact factor: 2.823

2.  Antiviral efficacy upon administration of a HepDirect prodrug of 2'-C-methylcytidine to hepatitis C virus-infected chimpanzees.

Authors:  Steven S Carroll; Kenneth Koeplinger; Marissa Vavrek; Nanyan Rena Zhang; Laurence Handt; Malcolm MacCoss; David B Olsen; K Raja Reddy; Zhili Sun; Paul D van Poelje; James M Fujitaki; Serge H Boyer; David L Linemeyer; Scott J Hecker; Mark D Erion
Journal:  Antimicrob Agents Chemother       Date:  2011-05-31       Impact factor: 5.191

3.  INX-08189, a phosphoramidate prodrug of 6-O-methyl-2'-C-methyl guanosine, is a potent inhibitor of hepatitis C virus replication with excellent pharmacokinetic and pharmacodynamic properties.

Authors:  John H Vernachio; Blair Bleiman; K Dawn Bryant; Stanley Chamberlain; Damound Hunley; Jeff Hutchins; Brenda Ames; Elena Gorovits; Babita Ganguly; Andrea Hall; Alexander Kolykhalov; Yule Liu; Jerry Muhammad; Nicholas Raja; C Robin Walters; Jin Wang; Karen Williams; Joseph M Patti; Geoffrey Henson; Karolina Madela; Mohamed Aljarah; Arnaud Gilles; Christopher McGuigan
Journal:  Antimicrob Agents Chemother       Date:  2011-02-28       Impact factor: 5.191

Review 4.  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

5.  Design, synthesis and biological evaluation of phosphorodiamidate prodrugs of antiviral and anticancer nucleosides.

Authors:  Christopher McGuigan; Claire Bourdin; Marco Derudas; Nadège Hamon; Karen Hinsinger; Sahar Kandil; Karolina Madela; Silvia Meneghesso; Fabrizio Pertusati; Michaela Serpi; Magdalena Slusarczyk; Stanley Chamberlain; Alexander Kolykhalov; John Vernachio; Christophe Vanpouille; Andrea Introini; Leonid Margolis; Jan Balzarini
Journal:  Eur J Med Chem       Date:  2013-10-09       Impact factor: 6.514

Review 6.  Phosphoramidates and phosphonamidates (ProTides) with antiviral activity.

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

Review 7.  A review on the development of urease inhibitors as antimicrobial agents against pathogenic bacteria.

Authors:  Yuri F Rego; Marcelo P Queiroz; Tiago O Brito; Priscila G Carvalho; Vagner T de Queiroz; Ângelo de Fátima; Fernando Macedo
Journal:  J Adv Res       Date:  2018-05-04       Impact factor: 10.479

Review 8.  Broad-Spectrum Antiviral Strategies and Nucleoside Analogues.

Authors:  Robert J Geraghty; Matthew T Aliota; Laurent F Bonnac
Journal:  Viruses       Date:  2021-04-13       Impact factor: 5.048

Review 9.  Inhibition of viral RNA polymerases by nucleoside and nucleotide analogs: therapeutic applications against positive-strand RNA viruses beyond hepatitis C virus.

Authors:  Jerome Deval; Julian A Symons; Leo Beigelman
Journal:  Curr Opin Virol       Date:  2014-09-17       Impact factor: 7.090

  9 in total

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