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Synthesis and Biological Evaluation of Pyridine-Containing Lipoxin A4 Analogues

  • Colm Duffy
Chapter
Part of the Springer Theses book series (Springer Theses)

Abstract

The development of stable LXA4 and LXB4 analogues which show resistance to enzymatic degradation is an on-going research goal in drug development.The development of stable LXA4 and LXB4 analogues which show resistance to enzymatic degradation is an on-going research goal in drug development. Efforts directed towards derivatisation of the triene system in particular have been inspired by the encouraging results obtained from the biological evaluation of our novel aromatic analogues [1], along with those of Petasis et al. [2, 3]. Rational replacement of this triene system has previously led to more stable derivatives, where enzymatic degradation is suppressed.

Keywords

Chiral HPLC Structure Activity Relationship Study Heck Coupling Pyridinium Chlorochromate Aromatic Analogue 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    O’Sullivan TP, Vallin KSA, Shah STA, Fakhry J, Maderna P, Scannell M, Sampaio ALF, Perretti M, Godson C, Guiry PJ (2007) J Med Chem 50:5894CrossRefGoogle Scholar
  2. 2.
    Petasis NA, Keledjian R, Sun Y-P, Nagulapalli KC, Tjonahen E, Yang R, Serhan CN (2008) Bioorg Med Chem Lett 18:1382CrossRefGoogle Scholar
  3. 3.
    Sun Y-P, Tjonahen E, Keledjian R, Zhu M, Yang R, Recchiuti A, Pillai PS, Petasis NA, Serhan CN (2009) Prostaglandins Leukotrienes Essent Fat Acids 81:357CrossRefGoogle Scholar
  4. 4.
    Maddox JF, Hachicha M, Takano T, Petasis NA, Fokin VV, Serhan CN (1997) J Biol Chem 272:6972CrossRefGoogle Scholar
  5. 5.
    Williams DA, Foye WO, Lemke TL (2002) In: Foye’s principles of medicinal chemistry, Lippincott Williams & Wilkins, 5th edn, 60Google Scholar
  6. 6.
    Patani GA, LaVoie EJ (1996) Chem Rev 96:3147CrossRefGoogle Scholar
  7. 7.
    Parsons ME, Ganellin CR (2006) Br J Pharmac 147:S127CrossRefGoogle Scholar
  8. 8.
  9. 9.
    Lind T, Rydberg L, Kylebäck A, Jonsson A, Andersson T, Hasselgren G, Holmberg J, Röhss K (2000) Aliment Pharmacol Ther 14:861CrossRefGoogle Scholar
  10. 10.
    Herzig SJ, Howell MD, Ngo LH, Marcantonio ER (2009) J Am Med Assoc 301:2120CrossRefGoogle Scholar
  11. 11.
    Colca JR, McDonald WG, Waldon DJ, Leone JW, Lull JM, Bannow CA, Lund ET, Mathews WR (2004) Am J Physiol Endocrinol Metab 286:E252CrossRefGoogle Scholar
  12. 12.
    Morii M, Takata H, Fujisaki H, Takegucht N (1990) Biochemical Pharmacol 39:661CrossRefGoogle Scholar
  13. 13.
    Duffy CD, Maderna P, McCarthy C, Loscher CE, Godson C, Guiry PJ (2010) Chem Med Chem 5:517Google Scholar
  14. 14.
    Gribble GW, Saulnier MG (1993) Heterocycles 35:151CrossRefGoogle Scholar
  15. 15.
    Gilman H, Spatz SM (1951) J Org Chem 16:1485CrossRefGoogle Scholar
  16. 16.
    Corey EJ, Suggs JW (1975) Tetrahedron Lett 16:2647CrossRefGoogle Scholar
  17. 17.
    Agarwal S, Tiwari HP, Sharma JP (1990) Tetrahedron 46:4417CrossRefGoogle Scholar
  18. 18.
    Aoyagi Y, Inariyama T, Arai Y, Tsuchida S, Matuda Y, Kobayashi H, Ohta A, Kurihara T, Fujihira S (1994) Tetrahedron 50:13575CrossRefGoogle Scholar
  19. 19.
    Heck RF (1968) J Am Chem Soc 90:5518CrossRefGoogle Scholar
  20. 20.
    Nicolaou KC, Bulger PG, Sarlah D (2005) Angew Chem Int Ed Engl 44:4442CrossRefGoogle Scholar
  21. 21.
    Coyne AG, Fitzpatrick MO, Guiry PJ (2009) In: Oestreich M (ed) The Mizoroki-Heck Reaction. p 405Google Scholar
  22. 22.
    Labelle M, Belley M, Gareau Y, Gauthier JY, Guay D, Gordon R, Grossman SG, Jones TR, Leblanc Y, McAuliffe M, McFarlane C, Masson P, Metters KM, Ouimet N, Patrick DH, Piechuta H, Rochette C, Sawyer N, Xiang YB, Pickett CB, Ford-Hutchinson AW, Zamboni RJ, Young RN (1995) Bioorg Med Chem Lett 5:283CrossRefGoogle Scholar
  23. 23.
    Singh S, Duffy CD, Shah STA, Guiry PJ (2008) J Org Chem 73:6429CrossRefGoogle Scholar
  24. 24.
    Zhang Y, Pavlova OA, Chefer SI, Hall AW, Kurian V, Brown LL, Kimes AS, Mukhin AG, Horti AG (2004) J Med Chem 47:2453CrossRefGoogle Scholar
  25. 25.
    Robert N, Hoarau C, Celanire S, Ribereau P, Godard A, Queguiner G, Marsais F (2005) Tetrahedron 61:4569CrossRefGoogle Scholar
  26. 26.
    Srebnik M, Ramachandran P, Brown H (1988) J Org Chem 53:2916CrossRefGoogle Scholar
  27. 27.
    Wu S-H, Liao PY, Dong L, Chen ZQ (2008) Inflamm Res 57:430CrossRefGoogle Scholar
  28. 28.
    Decker Y, McBean G, Godson C (2009) Am J Physiol Cell Physiol 296:C1420CrossRefGoogle Scholar
  29. 29.
    Aliberti J, Serhan C, Sher A (2002) J Exp Med 196:1253CrossRefGoogle Scholar
  30. 30.
    Sodin-Semrl S, Taddeo B, Tseng D, Varga J, Fiore S (2000) J Immunol 164:2660Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg  2012

Authors and Affiliations

  1. 1.UCD School of Chemistry and Chemical Biology, Centre for Synthesis and Chemical BiologyUniversity College DublinBelfield, Dublin 4Ireland

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