Literature DB >> 19948402

Synthesis and evaluation of 3'-azido-2',3'-dideoxypurine nucleosides as inhibitors of human immunodeficiency virus.

Hong-Wang Zhang1, Steven J Coats, Lavanya Bondada, Franck Amblard, Mervi Detorio, Ghazia Asif, Emilie Fromentin, Sarah Solomon, Aleksandr Obikhod, Tony Whitaker, Nicolas Sluis-Cremer, John W Mellors, Raymond F Schinazi.   

Abstract

Based on the promising drug resistance profile and potent anti-HIV activity of beta-d-3'-azido-2',3'-dideoxyguanosine, a series of purine modified nucleosides were synthesized by a chemical transglycosylation reaction and evaluated for their antiviral activity, cytotoxicity, and intracellular metabolism. Among the synthesized compounds, several show potent and selective anti-HIV activity in primary lymphocytes. Published by Elsevier Ltd.

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Year:  2009        PMID： 19948402      PMCID： PMC3089953          DOI： 10.1016/j.bmcl.2009.11.031

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


  19 in total

Review 1.  Antiretroviral therapy of HIV-1 infection: established treatment strategies and new therapeutic options.

Authors:  G R Kaufmann; D A Cooper
Journal:  Curr Opin Microbiol       Date:  2000-10       Impact factor: 7.934

Review 2.  Incidence and impact of resistance against approved antiretroviral drugs.

Authors:  D Pillay; S Taylor; D D Richman
Journal:  Rev Med Virol       Date:  2000 Jul-Aug       Impact factor: 6.989

3.  Structure-activity relationships of 2'-fluoro-2',3'-unsaturated D-nucleosides as anti-HIV-1 agents.

Authors:  Kyeong Lee; Yongseok Choi; Giuseppe Gumina; Wen Zhou; Raymond F Schinazi; Chung K Chu
Journal:  J Med Chem       Date:  2002-03-14       Impact factor: 7.446

4.  Treatment-limiting toxicities associated withnucleoside analogue reverse transcriptase inhibitor therapy: A prospective, observational study.

Authors:  Rosario Palacios; Jesús Santos; Xavier Camino; Piedad Arazo; Rafael Torres Perea; Santiago Echevarrfa; Esteban Ribera; Rainel Sánchez de la Rosa; Santiago Moreno Guillen
Journal:  Curr Ther Res Clin Exp       Date:  2005-03

5.  The 3'-azido group is not the primary determinant of 3'-azido-3'-deoxythymidine (AZT) responsible for the excision phenotype of AZT-resistant HIV-1.

Authors:  Nicolas Sluis-Cremer; Dominique Arion; Urvi Parikh; Dianna Koontz; Raymond F Schinazi; John W Mellors; Michael A Parniak
Journal:  J Biol Chem       Date:  2005-06-20       Impact factor: 5.157

6.  Characterization of human immunodeficiency viruses resistant to oxathiolane-cytosine nucleosides.

Authors:  R F Schinazi; R M Lloyd; M H Nguyen; D L Cannon; A McMillan; N Ilksoy; C K Chu; D C Liotta; H Z Bazmi; J W Mellors
Journal:  Antimicrob Agents Chemother       Date:  1993-04       Impact factor: 5.191

Review 7.  New nucleoside/nucleotide backbone options: a review of recent studies.

Authors:  Peter J Ruane; Edwin DeJesus
Journal:  J Acquir Immune Defic Syndr       Date:  2004-09-01       Impact factor: 3.731

8.  Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides.

Authors:  P Herdewijn; J Balzarini; M Baba; R Pauwels; A Van Aerschot; G Janssen; E De Clercq
Journal:  J Med Chem       Date:  1988-10       Impact factor: 7.446

9.  Nucleic acid related compounds. 57. Synthesis, x-ray crystal structure, lipophilic partition properties, and antiretroviral activities of anomeric 3'-azido-2',3'-dideoxy-2,6-diaminopurine ribosides.

Authors:  M J Robins; S G Wood; N K Dalley; P Herdewijn; J Balzarini; E De Clercq
Journal:  J Med Chem       Date:  1989-08       Impact factor: 7.446

10.  Design and synthesis of 3'- and 5'-O-(3-benzenesulfonylfuroxan-4-yl)-2'-deoxyuridines: biological evaluation as hybrid nitric oxide donor-nucleoside anticancer agents.

Authors:  Sameh Moharram; Aihua Zhou; Leonard I Wiebe; Edward E Knaus
Journal:  J Med Chem       Date:  2004-03-25       Impact factor: 7.446
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  3 in total

1.  Binding of novel fullerene inhibitors to HIV-1 protease: insight through molecular dynamics and molecular mechanics Poisson-Boltzmann surface area calculations.

Authors:  Haralambos Tzoupis; Georgios Leonis; Serdar Durdagi; Varnavas Mouchlis; Thomas Mavromoustakos; Manthos G Papadopoulos
Journal:  J Comput Aided Mol Des       Date:  2011-10-04       Impact factor: 3.686

2.  Synthesis, antiviral activity, cytotoxicity and cellular pharmacology of l-3'-azido-2',3'-dideoxypurine nucleosides.

Authors:  Hong-Wang Zhang; Mervi Detorio; Brian D Herman; Sarah Solomon; Leda Bassit; James H Nettles; Aleksandr Obikhod; Si-Jia Tao; John W Mellors; Nicolas Sluis-Cremer; Steven J Coats; Raymond F Schinazi
Journal:  Eur J Med Chem       Date:  2011-05-30       Impact factor: 6.514

3.  Substrate mimicry: HIV-1 reverse transcriptase recognizes 6-modified-3'-azido-2',3'-dideoxyguanosine-5'-triphosphates as adenosine analogs.

Authors:  Brian D Herman; Raymond F Schinazi; Hong-wang Zhang; James H Nettles; Richard Stanton; Mervi Detorio; Aleksandr Obikhod; Ugo Pradère; Steven J Coats; John W Mellors; Nicolas Sluis-Cremer
Journal:  Nucleic Acids Res       Date:  2011-09-13       Impact factor: 16.971
  3 in total

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