Literature DB >> 15975800

Efficient synthesis of fluorothiosparfosic acid analogues with potential antitumoral activity.

Emmanuel Pfund1, Thierry Lequeux, Serge Masson, Michel Vazeux, Alex Cordi, Alain Pierre, Valérie Serre, Guy Hervé.   

Abstract

In this paper, we describe a short synthesis of N-(phosphonoacetyl)-L-aspartate (PALA) analogues. The mono- and difluorinated thioacetamide precursors were prepared in one step from methyl (diethoxyphosphono)di- and monofluoromethyldithioacetates 8 and 11 as starting materials. Antiproliferating properties on a L1210 strain and ATCase inhibition of these new compounds are disclosed. ThioPALA(FF) 5c showed a remarkable cytotoxic activity towards murine leukemia L1210, when used as tetraester.

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Year:  2005        PMID： 15975800     DOI： 10.1016/j.bmc.2005.05.026

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


  7 in total

1.  Design, synthesis, and bioactivity of novel inhibitors of E. coli aspartate transcarbamoylase.

Authors:  Joby Eldo; Sabrina Heng; Evan R Kantrowitz
Journal:  Bioorg Med Chem Lett       Date:  2006-12-21       Impact factor: 2.823

2.  Thioamide hydroxypyrothiones supersede amide hydroxypyrothiones in potency against anthrax lethal factor.

Authors:  Arpita Agrawal; César Augusto F de Oliveira; Yuhui Cheng; Jennifer A Jacobsen; J Andrew McCammon; Seth M Cohen
Journal:  J Med Chem       Date:  2009-02-26       Impact factor: 7.446

3.  N-phosphonacetyl-L-isoasparagine a potent and specific inhibitor of Escherichia coli aspartate transcarbamoylase.

Authors:  Joby Eldo; James P Cardia; Elizabeth M O'Day; Jiarong Xia; Hiro Tsuruta; Evan R Kantrowitz
Journal:  J Med Chem       Date:  2006-10-05       Impact factor: 7.446

Review 4.  The alpha,alpha-difluorinated phosphonate L-pSer-analogue: an accessible chemical tool for studying kinase-dependent signal transduction.

Authors:  Kaushik Panigrahi; MariJean Eggen; Jun-Ho Maeng; Quanrong Shen; David B Berkowitz
Journal:  Chem Biol       Date:  2009-09-25

5.  Submicromolar phosphinic inhibitors of Escherichia coli aspartate transcarbamoylase.

Authors:  Laëtitia Coudray; Evan R Kantrowitz; Jean-Luc Montchamp
Journal:  Bioorg Med Chem Lett       Date:  2008-12-06       Impact factor: 2.823

6.  Synthesis and in vitro evaluation of aspartate transcarbamoylase inhibitors.

Authors:  Laëtitia Coudray; Anne F Pennebaker; Jean-Luc Montchamp
Journal:  Bioorg Med Chem       Date:  2009-09-30       Impact factor: 3.641

7.  Phosphonodithioester-Amine Coupling as a Key Reaction Step for the Design of Cationic Amphiphiles Used for Gene Delivery.

Authors:  Montassar Khalil; Alexis Hocquigny; Mathieu Berchel; Tristan Montier; Paul-Alain Jaffrès
Journal:  Molecules       Date:  2021-12-11       Impact factor: 4.411
  7 in total

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