30
Views
0
CrossRef citations to date
0
Altmetric
Original Research

Pharmacological characterization of oxime agonists of the histamine H4 receptor

, , , , , , & show all
Pages 37-49 | Published online: 16 Dec 2009

References

  • Thurmond RL, Gelfand EW, Dunford PJ. The role of histamine H and H4 receptors in allergic inflammation: the search for new antihistamines. Nat Rev Drug Discov. 2008;7(1):41–53.
  • Edwards MP, Doherty AM, Ley SV, Organ HM. Preparation of 2-substituted pyrroles and indoles by regioselective alkylation and deprotection of 1-(2-trimethylsilylethoxymethyl)pyrrole and 1-(2-trim ethylsilylethoxymethyl)indole. Tetrahedron. 1986;42(13):3723–3729.
  • Zhang D, Kohlman D, Krushinski J, et al. Design, synthesis and evaluation of bicyclic benzamides as novel 5-HT1F receptor agonists. Bioorg Med Chem Lett. 2004;14(24):6011–6016.
  • Cain GA, Teleha CA. A convenient synthesis of N-Boc -4-formylpiperidine. Org Prep ProcedInt. 2000;32(1):96–99.
  • Nahm S, Weinreb SM. N-Methoxy-N-methylamides as effective acylating agents. Tetrahedron Lett. 1981;22(39):3815–3818.
  • Clarke HT, Gillespie HB, Weisshaus SZ. Action of formaldehyde on amines and amino acids. J Am Chem Soc. 1933;55:4571–4587.
  • Moore ML. Leuckart reaction. Org Reactions. 1949;5:301–330.
  • Phinney KW. Enantioselective separations by packed column subcritical and supercritical fluid chromatography. Anal Bioanal Chem. 2005;382(3):639–645.
  • Hawkes GE, Herwig K, Roberts JD. Nuclear magnetic resonance spectroscopy. Use of carbon-13 spectra to establish configurations of oximes. J Org Chem. 1974;39(8):1017–1028.
  • Saulnier MG, Gribble GW Generation and reactions of 3-lithio-1- (phenylsulfonyl)indole. J Org Chem. 1982;47(5):757–761.
  • Hofstra CL, Desai PJ, Thurmond RL, Fung-Leung WP Histamine H4 receptor mediates chemotaxis and calcium mobilization of mast cells. J Pharmacol Exp Ther. 2003;305(3):1212–1221.
  • Jablonowski JA, Grice CA, Chai W, et al. The first potent and selective non-imidazole human histamine H4 receptor antagonists. J Med Chem. 2003;46(19):3957–3960.
  • Thurmond RL, Desai PJ, Dunford PJ, et al. A potent and selective histamine H4 receptor antagonist with anti-inflammatory properties. J Pharmacol Exp Ther. 2004;309(1):404–413.
  • Jiang W, Lim HD, Zhang M, et al. Cloning and pharmacological characterization of the dog histamine H4 receptor. Eur J Pharmacol. 2008;592(1–3):26–32.
  • Liu C, Ma XJ, Jiang X, et al. Cloning and pharmacological characterization of a fourth histamine receptor (H4) expressed in bone marrow. Mol Pharmacol. 2001;59(3):420–426.
  • Liu C, Wilson SJ, Kuei C, Lovenberg TW Comparison of human, mouse, rat, and guinea pig histamine H4 receptors reveals substantial pharmacological species variation. J Pharmacol Exp Ther. 2001;299(1):121–130.
  • Leurs R, Smit MJ, Menge WM, Timmerman H. Pharmacological characterization of the human histamine H2 receptor stably expressed in Chinese hamster ovary cells. Br J Pharmacol. 1994;112(3):847–854.
  • Cheng YC, Prusoff WH. Relation between the inhibition constant K1) and the concentration of inhibitor which causes fifty per cent inhibition (I50) of an enzymic reaction. Biochem Pharmacol. 1973;22(23):3099–3108.
  • Ling P, Ngo K, Nguyen S, et al Histamine H4 receptor mediates eosinophil chemotaxis with cell shape change and adhesion molecule upregulation. Br J Pharmacol. 2004;142(1):161–171.
  • Dunford PJ, Williams KN, Desai PJ, Karlsson L, McQueen D, Thurmond RL. Histamine H4 receptor antagonists are superior to traditional antihistamines in the attenuation of experimental pruritus. J Allergy Clin Immunol. 2007;119(1):176–183.
  • Bell JK, McQueen DS, Rees JL. Involvement of histamine H4 and H1 receptors in scratching induced by histamine receptor agonists in BalbC mice. Br J Pharmacol. 2004;142:374–380.
  • Huang JF, Thurmond R. The new biology of histamine receptors. Curr Allergy Asthma Rep. 2008;8(1):21–27.
  • Schneider E, Machavoine F, Pleau JM, et al. Organic cation transporter 3 modulates murine basophil functions by controlling intracellular histamine levels. J Exp Med. 2005;202(3):387–393.
  • Lim HD, van Rijn RM, Ling P, Bakker RA, Thurmond RL, Leurs R. Evaluation of histamine H1-, H2-, and H3-receptor ligands at the human histamine H4 receptor: Identification of 4-methylhistamine as the first potent and selective H4 receptor agonist. J Pharmacol Exp Ther. 2005;314(3):1310–1321.
  • Lim HD, Adami M, Guaita E, et al. Pharmacological characterization of the new histamine H4 receptor agonist VUF 8430. Br J Pharmacol. 2009;157(1):34–43.
  • Sugata Y, Okano M, Fujiwara T, et al. Histamine H4 receptor agonists have more activities than H4 agonism in antigen-specific human T-cell responses. Immunology. 2007;121(2):266–275.
  • Lim HD, Graaf CD, Jiang W, et al. Molecular basis of pharmacological differences among the H4R species variants. Mol Pharmacol. 2009; Submitted.
  • Kenakin T. Principles: Receptor theory in pharmacology. Trends Pharmacol Sci. 2004;25(4):186–192.
  • Sabroe I, Hartnell A, Jopling LA, et al. Differential regulation of eosinophil chemokine signaling via CCR3 and non-CCR3 pathways. J Immunol. 1999;162(5):2946–2955.
  • Venable JD, Cai H, Chai W, et al. Preparation and biological evaluation of indole, benzimidazole, and thienopyrrole piperazine carboxamides: Potent human histamine H4 antagonists. J Med Chem. 2005;48(26):8289–8298.