Literature DB >> 19282192

Aryl nucleoside H-phosphonates. Part 16: synthesis and anti-HIV-1 activity of di-aryl nucleoside phosphotriesters.

Joanna Romanowska1, Agnieszka Szymańska-Michalak, Jerzy Boryski, Jacek Stawiński, Adam Kraszewski, Roberta Loddo, Giuseppina Sanna, Gabriella Collu, Barbara Secci, Paolo La Colla.   

Abstract

Di-aryl nucleoside phosphotriesters have been explored as a new type of pronucleotides for the purpose of anti-HIV-1 therapy and efficient synthetic protocols, based on H-phosphonate chemistry, have been developed for the preparation of this class of compounds. It was found that anti-HIV-1 activity of the phosphotriesters bearing an antiviral nucleoside moiety (AZT, ddA) and also ddU was due, at least partially, to intracellular conversion into the corresponding nucleoside 5'-monophosphates, and their efficiency correlated well with the pK(a) values of the aryloxy groups present.

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Year:  2009        PMID: 19282192     DOI: 10.1016/j.bmc.2009.02.033

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  4 in total

Review 1.  Prodrugs of phosphonates and phosphates: crossing the membrane barrier.

Authors:  Andrew J Wiemer; David F Wiemer
Journal:  Top Curr Chem       Date:  2015

2.  Mixed Aryl Phosphonate Prodrugs of a Butyrophilin Ligand.

Authors:  Benjamin J Foust; Michael M Poe; Nicholas A Lentini; Chia-Hung Christine Hsiao; Andrew J Wiemer; David F Wiemer
Journal:  ACS Med Chem Lett       Date:  2017-08-09       Impact factor: 4.345

3.  The case of triethylammonium cation loss during purification of certain nucleotide analogues: a cautionary note.

Authors:  Krystian Kolodziej; Joanna Romanowska; Jacek Stawinski; Adam Kraszewski; Michal Sobkowski
Journal:  Anal Bioanal Chem       Date:  2014-12-27       Impact factor: 4.142

Review 4.  H-Phosphonate Chemistry in the Synthesis of Electrically Neutral and Charged Antiviral and Anticancer Pronucleotides.

Authors:  Adam Kraszewski; Michal Sobkowski; Jacek Stawinski
Journal:  Front Chem       Date:  2020-11-13       Impact factor: 5.221

  4 in total

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