David Virieux

Publications (11) View all

• Article: Synthesis of a new family of acyclic nucleoside phosphonates, analogues of TPases transition states.

  Bénédicte Dayde, Samira Benzaria, Claire Pierra, Gilles Gosselin, Dominique Surleraux, Jean-Noël Volle, Jean-Luc Pirat, David Virieux
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  ABSTRACT: A 6-step procedure was developed for the synthesis of a new family of acyclic nucleoside phosphonates (ANPs), "PHEEPA" [(2-pyrimidinyl-2-(2-hydroxyethoxy)ethyl)phosphonic acids] in overall yields ranging from 4.5% to 32%. These compounds, which possess on one side a hydroxy function and on the other side a phosphonate group, can be considered either as potential antiviral agents or as transition state analogues of nucleoside phosphorylases such as thymidine phosphorylase.
  Organic & Biomolecular Chemistry 03/2012; 10(17):3448-54. · 3.70 Impact Factor
• Article: Highly convergent synthesis of chiral bicyclophosphinates by domino hydrophosphinylation/Michael/Michael reaction.

  Pierre Fourgeaud, Bénédicte Daydé, Jean-Noël Volle, Jean-Pierre Vors, Arie Van der Lee, Jean-Luc Pirat, David Virieux
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  ABSTRACT: Diastereoselective domino reactions of iminoalcohols and allenyl H-phosphinates produce chiral phosphorus bicycles in a regio- and stereoselective fashion. A predictive model for diastereoselection is used for these new chiral phosphinic esters.
  Organic Letters 09/2011; 13(19):5076-9. · 5.86 Impact Factor
• Article: Drug discovery: phosphinolactone, in vivo bioisostere of the lactol group.

  Jean-Noël Volle, Damien Filippini, Bartlomiej Krawczy, Nikolay Kaloyanov, Arie Van der Lee, Tangui Maurice, Jean-Luc Pirat, David Virieux
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  ABSTRACT: In drug discovery, structural modifications over the lead molecule are often crucial for the development of a drug. Herein, we reported the first in vivo bioisosteric effect of phosphinolactone function in relation to the lactol group constituting the bioactive molecule: Hydroxybupropion. The preparation of phosphinolactone analogues and their antidepressant evaluation towards forced swimming test in mice showed that biological activity was regained and even strengthen.
  Organic & Biomolecular Chemistry 03/2010; 8(6):1438-44. · 3.70 Impact Factor
• Source

  Available from: Matthieu Starck

  Article: Chiral phosphinyl analogues of 2-C-arylmorpholinols:2-aryl-3,5-diphenyl-[1,4,2]-oxazaphosphinanes

  matthieu starck, Jean-Luc Pirat, David Virieux, Jean-Noël Volle, Ludovic Clarion, Jérome Monbrun
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  ABSTRACT: (2R,3R,5R)-2-Aryl-3,5-diphenyl-[1,4,2]-oxazaphosphinanes 6, analogues of C-arylmorpholinol 3, were prepared with diastereomeric excess higher than 94%, via a three step sequence: (i) diastereoselective addition–cyclization reaction from methyl hypophosphite and a chiral imine 10, (ii) pallado-catalyzed arylation, and then (iii) a selective inversion of configuration at the phosphorus center.
  Tetrahedron Asymmetry 05/2006; 17(9):1402. · 2.65 Impact Factor
• Article: 1H and 13C NMR identification of unexpected 3,4-dihydroquinoxalines in the syntheses of 1,5-benzodiazepine derivatives.

  E M Tjiou, E G Lhoussaine, D Virieux, A Fruchier
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  ABSTRACT: The reaction between o-phenylenediamines, dehydroacetic acid and aromatic aldehydes is shown to give not only the expected 1,5-benzodiazepine derivative but also a 3,4-dihydroquinoxaline, the structure of which was determined by its 1H and 13C 1D and 2D NMR spectra.
  Magnetic Resonance in Chemistry 08/2005; 43(7):557-62. · 1.44 Impact Factor