Synthesis and Pharmacological Identification of Neutral Histamine H 1-Receptor Antagonists

Journal of Medicinal Chemistry

Volumn 46, Issue 26, 2003, Pages 5812-5824

  Govoni, Marinella ^a   Bakker, Remko A ^a   Van De Wetering, Ineke ^a   Smit, Martine J ^a   Menge, Wiro M B P ^a   Timmerman, Henk ^a   Elz, Sigurd ^b   Schunack, Walter ^c   Leurs, Rob ^a  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

^b UNIVERSITY OF REGENSBURG   (Germany)

^c FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

10 (1H IMIDAZOL 4 YL)DECYLAMINE; 2 [2 (4,4 DIPHENYLBUTYL) 1H IMIDAZOL 4 YL]ETHYLAMINE; 2 [2 (5,5 DIPHENYLPENTYL) 1H IMIDAZOL 4 YL]ETHYLAMINE; HISTAMINE; HISTAMINE H1 RECEPTOR; HISTAMINE H1 RECEPTOR ANTAGONIST; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; RADIOLIGAND; UNCLASSIFIED DRUG; VUF 4734;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; RECEPTOR AFFINITY; REPORTER GENE;

ANIMALS; BINDING, COMPETITIVE; CELL LINE; CERCOPITHECUS AETHIOPS; GENES, REPORTER; HISTAMINE; HISTAMINE AGONISTS; HISTAMINE H1 ANTAGONISTS; HUMANS; INOSITOL PHOSPHATES; LIGANDS; NF-KAPPA B; RADIOLIGAND ASSAY; RECEPTORS, G-PROTEIN-COUPLED; RECEPTORS, HISTAMINE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0345735308     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030936t     Document Type: Article

References (72)

1. 1 receptor. Biochem. Biophys. Res. Commun. 1993, 197, 1601-1608.
2. 1 receptor gene. Biochem. Biophys. Res. Commun. 1994, 201, 894-901.
3. 1-histamine-receptor cDNA in Chinese hamster ovary cells. Pharmacological characterisation of the protein, tissue distribution of messenger RNA and chromosomal localisation of the gene. Eur. J. Biochem. 1994, 224, 489-495.
4. 2 receptor. Biochem. Biophys. Res. Commun. 1991, 178, 1386-1392.
5. 3 receptor. Mol. Pharmacol. 1999, 55, 1101-1107.
6. Zhu, Y.; Michalovich, D.; Wu, H. L.; Tan, K. B.; Dytko, G. M.; Mannan, I. J.; Boyce, R.; Alston, J.; Tierney, L. A.; Li, X.; Herrity, N. C.; Vawter, L.; Sarau, H. M.; Ames, R. S.; Davenport, C. M.; Hieble, J. P.; Wilson, S.; Bergsma, D. J.; Fitzgerald, L. R. Cloning, Expression, and Pharmacological Characterization of a Novel Human Histamine Receptor. Mol. Pharmacol. 2001, 59, 434-441.
7. 4) Expressed in Bone Marrow. Mol. Pharmacol. 2001, 59, 420-426.
8. Oda, T.; Morikawa, N.; Saito, Y.; Masuho, Y.; Matsumoto, S. Molecular cloning and characterization of a novel type of histamine receptor preferentially expressed in leukocytes. J. Biol. Chem. 2000, 275, 36781-36786.
9. Nakamura, T.; Itadani, H.; Hidaka, Y.; Ohta, M.; Tanaka, K. Molecular cloning and characterization of a new human histamine receptor, HH4R. Biochem. Biophys. Res. Commun. 2000, 279, 615-620.
10. Morse, K. L.; Behan, J.; Laz, T. M.; West, R. E.; Greenfeder, S. A.; Anthes, J. C.; Umland, S.; Wan, Y.; Hipkin, R. W.; Gonsiorek, W.; Shin, N.; Gustafson, E. L.; Qiao, X.; Wang, S.; Hedrick, J. A.; Greene, J.; Bayne, M.; Monsma, F. J. Cloning and Characterization of a Novel Human Histamine Receptor. J. Pharmacol. Exp. Ther. 2001, 296, 1058-1066.
11. Dale, H. H.; Laidlaw, P. P. The Physiological Action of β-imidazolylethylamine. J. Physiol. 1910, 41, 418-444.
12. 1-receptor antagonists. Burger's Medicinal Chemistry and Drug Discovery, 5th ed.; John Wiley & Sons: New York, 1997; pp 495-559.
13. Costa, T.; Ogino, Y.; Munson, P. J.; Onaran, H. O.; Rodbard, D. Drug efficacy at guanine nucleotide-binding regulatory protein-linked receptors: Thermodynamic interpretation of negative antagonism and of receptor activity in the absence of ligand. Mol. Pharmacol. 1992, 41, 549-560.
14. Schutz, W.; Freissmuth, M. Reverse intrinsic activity of antagonists on G protein-coupled receptors. Trends Pharmacol. Sci. 1992, 13, 376-380.
15. Lefkowitz, R. J.; Cotecchia, S.; Samama, P.; Costa, T. Constitutive activity of receptors coupled to guanine nucleotide regulatory proteins. Trends Pharmacol. Sci. 1993, 14, 303-307.
16. Milligan, G.; Bond, R. A.; Lee, M. Inverse agonism: Pharmacological curiosity or potential therapeutic strategy? Trends Pharmacol. Sci. 1995, 16, 10-13.
17. Kenakin, T. The classification of seven transmembrane receptors in recombinant expression systems. Pharmacol. Rev. 1996, 48, 413-463.
18. Leurs, R.; Smit, M. J.; Alewijnse, A. E.; Timmerman, H. Agonist-independent regulation of constitutively active G-protein-coupled receptors. Trends Biochem. Sci. 1998, 23, 418-422.
19. 2 receptors. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 6802-6807.
20. 3 Antagonists. J. Pharmacol. Exp. Ther. 2001, 299, 908-914.
21. 3 receptors regulates histamine neurons in brain. Nature (London) 2000, 408, 860-864.
22. Shenker, A.; Laue, L.; Kosugi, S.; Merendino, J. J., Jr.; Minegishi, T.; Cutler, G. B., Jr. A constitutively activating mutation of the luteinizing hormone receptor in familial male precocious puberty. Nature (London) 1993, 365, 652-654.
23. Robinson, P. R.; Cohen, G. B.; Zhukovsky, E. A.; Oprian, D. D. Constitutively active mutants of rhodopsin. Neuron 1992, 9, 719-725.
24. Parma, J.; Duprez, L.; Van Sande, J.; Cochaux, P.; Gervy, C.; Mockel, J. ; Dumont, J.; Vassart, G. Somatic mutations in the thyrotropin receptor gene cause hyperfunctioning thyroid adenomas. Nature (London) 1993, 365, 649-651.
25. Robbins, L. S.; Nadeau, J. H.; Johnson, K. R.; Kelly, M. A.; Roselli-Rehfuss, L.; Baack, E.; Mountjoy, K. G.; Cone, R. D. Pigmentation phenotypes of variant extension locus alleles result from point mutations that alter MSH receptor function. Cell 1993, 72, 827-834.
26. Spiegel, A. M. Defects in G protein-coupled signal transduction in human disease. Annu. Rev. Physiol. 1996, 58, 143-170.
27. 1 receptor antagonists. Eur. J. Pharmacol. 2000, 387, R5-R7.
28. q/11-subunits in constitutive and agonist-mediated signaling. Mol. Pharmacol. 2001, 60, 1133-1142.
29. Costa, T.; Herz, A. Antagonists with negative intrinsic activity at delta opioid receptors coupled to GTP-binding proteins. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 7321-7325.
30. 2 dopamine receptor in a reconstituted system. J. Biol. Chem. 1990, 265, 4507-4514.
31. o. J. Biol. Chem. 1991, 266, 22285-22289.
32. Burstein, E. S.; Spalding, T. A.; Brann, M. R. Pharmacology of muscarinic receptor subtypes constitutively activated by G proteins. Mol. Pharmacol. 1997, 51, 312-319.
33. q. FEBS Lett. 1995, 363, 261-263.
34. Casarosa, P.; Bakker, R. A.; Verzijl, D.; Navis, M.; Timmerman, H.; Leurs, R.; Smit, M. J. Constitutive Signaling of the Human Cytomegalovirus-encoded Chemokine Receptor US28. J. Biol. Chem. 2001, 276, 1133-1137.
35. 2-adrenergic receptor. Extending the ternary complex model. J. Biol. Chem. 1993, 268, 4625-4636.
36. 1B-adrenergic receptor enhances mitogenesis and tumorigenicity. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 11354-11358.
37. Dosil, M.; Giot, L.; Davis, C.; Konopka, J. B. Dominant-negative mutations in the G-protein-coupled alpha-factor receptor map to the extracellular ends of the transmembrane segments. Mol. Cell. Biol. 1998, 18, 5981-5991.
38. 1B-adrenergic receptor signal-inactivating point mutation. EMBO J. 2000, 19, 4265-4271.
39. 1 receptor mRNA in allergic rhinitis. Clin. Exp. Allergy 1996, 26, 379-385.
40. Chiba, Y.; Saitoh, N.; Matsuo, K.; Misawa, M. Elevated nasal mucosal G protein levels and histamine receptor affinity in a guinea pig model of nasal hyperresponsiveness. Int. Arch. Allergy Immunol. 2002, 127, 285-293.
41. Milligan, G.; Bond, R. A. Inverse agonism and the regulation of receptor number. Trends Pharmacol. Sci. 1997, 18, 468-474.
42. 2-adrenoceptor antagonists. Eur. J. Pharmacol. 1989, 173, 85-92.
43. Homcy, C. J.; Vatner, S. F.; Vatner, D. E. Beta-adrenergic receptor regulation in the heart in pathophysiologic states: Abnormal adrenergic responsiveness in cardiac disease. Annu. Rev. Physiol. 1991, 53, 137-159.
44. Yoburn, B. C.; Duttaroy, A.; Shah, S.; Davis, T. Opioid antagonist-induced receptor upregulation: Effects of concurrent agonist administration. Brain Res. Bull. 1994, 33, 237-240.
45. Nwokolo, C. U.; Smith, J. T.; Sawyerr, A. M.; Pounder, R. E. Rebound intragastric hyperacidity after abrupt withdrawal of histamine H2 receptor blockade. Gut 1991, 32, 1455-1460.
46. Merki, H. S.; Wilder-Smith, C. H. Do continuous infusions of omeprazole and ranitidine retain their effect with prolonged dosing? Gastroenterology 1994, 106, 60-64.
47. Ngochindo, R. I. 2-Protecting Groups for 5-Lithiation in the Syntheses of Imidazoles. J. Chem. Soc., Perkin Trans. 1 1990, 6, 1645-1648.
48. Mitsunobu, O. The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products. Synthesis 1981, 1-28.
49. Gibson, M. S.; Bradshaw, R. W. Gabriel-Synthese Primärer. Amine. Angew. Chem. 1968, 80, 986-996.
50. Horne, D. A.; Yakushijin, K.; Büchi, G. A Two-Step Synthesis of Imidazoles From Aldehydes Via 4-Tosyloxazolines. Heterocycles 1994, 39, 139-153.
51. Loudon, G. M.; Radhakrishna, A. S.; Almond, M. R.; Blodgett, J. K.; Boutin, R. H. Conversion of Aliphatic Amides into Amines with [I,I-Bis(trifluoroacetoxy)iodo]benzene. 1. Scope of the Reaction. J. Org. Chem. 1984, 49, 4272-4276.
52. Brandsma, L. Metalation of Heterocyclic Compounds. Preparative Polar Organometallic Chemistry; Springer-Verlag: Berlin, 1990; Chapter 6, pp 127-139.
53. 3 antagonist, 4(5)-(5-aminopentyl)-1H-imidazole. J. Med. Chem. 1995, 38, 266-271.
54. Walter, L. A.; Hunt, W. H.; Fosbinder, R. J. J. Am. Chem. Soc. 1941, 63, 2771.
55. 1-receptor agonists. Prog. Drug Res. 1995, 44, 49-85.
56. 1 receptor agonist activity of a series of 2-phenyl-histamines, 2-heteroarylhistamines, and analogues. J. Med. Chem. 1995, 38, 1287-1294.
57. 116 (TM3) has a constitutive role in receptor stimulation. J. Comput. Aid. Mol. Design. 1995, 9, 319-330.
58. 1-receptor agonists. J. Med. Chem. 2000, 43, 1071-1084.
59. 1 receptors: Synthesis and structure-activity relationships. Eur. J. Med. Chem. 2000, 35, 41-52.
60. 1 receptor ligands. Part I. Novel thiazol-4-ylethanamine derivatives: Synthesis and in vitro pharmacology. Farmaco 1999, 54, 533-541.
61. 1 receptor ligands: Part II. Synthesis and in vitro pharmacology of 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives. Farmaco 2000, 55, 569-574.
62. 1-Antagonists and Including a Known Interaction Site on the Receptor. J. Med. Chem. 1995, 38, 3351-3360.
63. 1 Receptor: Synthesis and Structure-activity Relationships. Eur. J. Med. Chem. 2000, 35, 41-52.
64. 2C receptor systems. Mol. Pharmacol. 1999, 55, 863-872.
65. Lavreysen, H.; Le Poul, E.; Van Gompel, P.; Dillen, L.; Leysen, J. E.; Lesage, A. S. J. Supersensitivity of Human Metabotropic Glutamate la Receptor Signaling in L929sA Cells. Mol. Pharmacol. 2002, 61, 1244-1254.
66. 1 receptor. Mol. Pharmacol. 1983, 23, 60-66.
67. 1 receptor. J. Biol. Chem. 1999, 274, 29994-30000.
68. Ahmad, K.; Strong, F. M. The Synthesis of Unsaturated Fatty Acids. J. Am. Chem. Soc. 1948, 70, 1699-1700.
69. Carbelleira, N.; Thompson, J. E.; Ayanoglu, E.; Djerassi, C. Biosynthetic Studies of Marine Lipids. 5. The Biosynthesis of Long-Chain Branched Fatty Acids in Marine Sponges. J. Org. Chem. 1986, 51, 2751-2756.
70. Heiser, U. F.; Dobner, B. Copper-catalysed Coupling of Undec-10-enylmagnesium Bromide with ω-Functionalised Halogeno-alkanes as a Key Reaction for the Synthesis of Novel Bipolar Phospholipids with Different Headgroups and Chain Length. J. Chem. Soc., Perkin Trans. 1 1997, 1, 805-815.
71. Cundy, D. J.; Gurr, P. A. An Improved Synthesis of ± 18-methyleicosanoic acid. Org. Prep. Proced. Int. 2000, 32, 461-468.
72. Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 1976, 72, 248-254.