PDF herunterladen
Synthesis 2012(7): 1090-1094  
DOI: 10.1055/s-0031-1289719
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Extending Triazolyl-Based Release under Mildly Acidic Conditions To Give Aniline Derivatives

Régis Delatouche, Christian Bachmann, Gilles Frapper, Philippe Bertrand*
Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), UMR 7285 CNRS-Université de Poitiers, 4 rue Michel Brunet, Bâtiment B27, 86022 Poitiers cedex, France
Fax: +33(5)49453501; e-Mail: philippe.bertrand@univ-poitiers.fr;
Weitere Informationen

Publikationsverlauf

Received 8 December 2011
Publikationsdatum:
24. Februar 2012 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

Triazolyl derivatives of anilines were prepared and evaluated as releasing systems at mildly acidic pH values. Two triazolyl derivatives showed convenient pH sensitivity, being stable at pH 7.3 and rapidly hydrolyzed at pH values below 5. A generalized mechanism is proposed from additional theoretical investigations.

Key words

hydrolysis - alkynes - azides - cycloaddition - amines - protonation

    References

  • 1 White S. Szewczyk JW. Turner JM. Baird EE. Dervan PB. Nature  1998,  391:  468 
    Google Scholar
  • 2 Maeda H. Bioconjugate Chem.  2010,  21:  797 
    Google Scholar
  • 3 Zhang H. Wang G. Yang H. Expert Opin. Drug Delivery  2011,  8:  171 
    Google Scholar
  • 4a Patel VF. Hardin JN. Mastro JM. Law KL. Zimmermann JL. Ehlhardt WJ. Woodland JM. Starling JJ. Bioconjugate Chem.  1996,  7:  497 
    Google Scholar
  • 4b Fréchet JMJ. Gillies ER. Goodwin AP. Bioconjugate Chem.  2004,  15:  1254 
    Google Scholar
  • 5 Delatouche R. Mondon M. Gil A. Frapper G. Bachmann C. Bertrand P. Tetrahedron  2011,  67:  401 
    Google Scholar
  • 6 Mondon M. Delatouche R. Bachmann C. Frapper G. Len C. Bertrand P. Eur. J. Org. Chem.  2011,  2111 
    Google Scholar
  • 7a Huisgen R. Angew. Chem., Int. Ed. Engl.  1963,  2:  565 
    Google Scholar
  • 7b Huisgen R. Angew. Chem., Int. Ed. Engl.  1963,  2:  633 
    Google Scholar
  • 7c Kolb HC. Finn MG. Sharpless KB. Angew. Chem. Int. Ed.  2001,  40:  2004 
    Google Scholar
  • 7d Bertrand P. Gesson J.-P.
    J. Org. Chem.  2007,  72:  3596 
    Google Scholar
  • 8 Gooding OW. Beard CC. Jackson DY. Wren DL. Cooper GF. J. Org. Chem.  1991,  56:  1083 
    Google Scholar
  • 9 Streidl N. Antipova A. Mayr H. J. Org. Chem.  2009,  74:  7328 
    Google Scholar
  • 10 Bertrand P. Eur. J. Med. Chem.  2010,  45:  2095 
    Google Scholar
  • 11 Ringdahl B. Tetrahedron  1979,  35:  2413 
    Google Scholar