H3-receptor antagonists: Synthesis and structure-activity relationships of para- and meta-substituted 4(5)-phenyl-2-[[2-[4(5)-imidazolyl] ethyl]thio]imidazoles

Journal of Medicinal Chemistry

Volumn 40, Issue 16, 1997, Pages 2571-2578

  Mor, Marco ^a   Bordi, Fabrizio ^a   Silva, Claudia ^a   Rivara, Silvia ^a   Crivori, Patrizia ^a   Plazzi, Pier Vincenzo ^a   Ballabeni, Vigilio ^a   Caretta, Antonio ^a   Barocelli, Elisabetta ^a   Impicciatore, Mariannina ^a   Carrupt, Pierre Alain ^b   Testa, Bernard ^b  

^a UNIVERSITY OF PARMA   (Italy)

^b UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

4(5) PHENYL 2 [[2 (4(5) IMIDAZOLYL)ETHYL]THIO]IMIDAZOLE; HISTAMINE H3 RECEPTOR ANTAGONIST; UNCLASSIFIED DRUG; ALPHA METHYLHISTAMINE; ALPHA-METHYLHISTAMINE; ANTIHISTAMINIC AGENT; DIMAPRIT; HISTAMINE DERIVATIVE; HISTAMINE H3 RECEPTOR; IMIDAZOLE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; GUINEA PIG; LIPOPHILICITY; NEUROTRANSMISSION; NONHUMAN; PH; PROTON TRANSPORT; RAT; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION; ANIMAL; BINDING COMPETITION; BRAIN CORTEX; ELECTROSTIMULATION; EVOKED RESPONSE; ILEUM; METABOLISM; SYNTHESIS; WISTAR RAT;

ANIMALS; BINDING, COMPETITIVE; CEREBRAL CORTEX; DIMAPRIT; ELECTRIC STIMULATION; EVOKED POTENTIALS; GUINEA PIGS; HISTAMINE ANTAGONISTS; ILEUM; IMIDAZOLES; METHYLHISTAMINES; RATS; RATS, WISTAR; RECEPTORS, HISTAMINE H3; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030611265     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970070p     Document Type: Article

References (49)

1. Arrang, J.-M.; Garbarg, M.; Schwartz, J. C. Auto-Inhibition of Brain Histamine Release Mediated by a Novel Class (H3) of Histamine Receptor. Nature 1983, 302, 832-837.
2. 3 Heteroreceptors. Fundam. Clin. Pharmacol. 1994, 8, 128-137.
3. 3 Receptor Subtypes. Br. J. Pharmacol. 1992, 107, 919-923.
4. 3 Antagonist, Decreased Seizure Susceptibility of Electrically Induced Convulsions in Mice. Methods Find. Exp. Clin. Pharmacol. 1995, 17 (Suppl. C), 70-73.
5. Yokoyama, H.; Iinuma, K. Histamine and seizures - Implications for the Treatment of Epilepsy. CNS Drugs 1996, 5, 321-330.
6. Timmerman, H. Pharmacotherapy of Vertigo: Any News to be Expected? Acta Oto-Laryngol., Suppl. 1994, 513, 28-32.
7. Prast, H.; Argyriou, H.; Philippu, A. Histaminergic Neurons Facilitate Social Memory in Rats. Brain Res. 1996, 734, 316-318.
8. 3-Receptor Antagonist, on a Scopolamine-Induced Learning Deficit Using an Elevated Plus-Maze Test in Mice. Life Sci. 1995, 57, 2137-2144.
9. Sakata, T. Histamine Receptor and its Regulation of Energy Metabolism. Obes. Res. 1995, 3 (Suppl. 4), S541-S548.
10. 3 Receptor. Prog. Drug Res. 1995, 45, 107-165.
11. 3-Receptor Ligands. J. Pharm. Belg. 1995, 50, 179-187.
12. 3-Receptor: New Potent Antagonists of the 2-Thioimidazole Type. Il Farmaco, in press.
13. 3-Receptors. Nature 1987, 327, 117-123.
14. 3-Receptor. Eur. J. Med. Chem. 1992, 27, 511-517.
15. 125I]Iodophenpropit, to Rat Brain. Br. J. Pharmacol. 1994, 113, 355-362.
16. 3 Receptors. J. Pharmacol. Exp. Ther. 1994, 271, 452-459.
17. 3-Receptor Histamine Antagonists. J. Med. Chem. 1995, 38, 3342-3350.
18. 3-Receptor Affinity. Eur. J. Med. Chem. 1995, 30, 881-889.
19. 3 Receptor Antagonists. Bioorg. Med. Chem. Lett. 1996, 6, 833-838.
20. 3-Receptor Antagonist Thioperamide. J. Pharm. Pharmacol. 1996, 48, 712-717.
21. Bordi, F.; Mor, M.; Morini, G.; Plazzi, P. V.; Silva, C.; Vitali, T.; Caretta, A. QSAR Study on H3-Receptor Affinity of Benzothiazole Derivatives of Thioperamide. Il Farmaco 1994, 49, 153-166.
22. Barocelli, E.; Ballabeni, V.; Chiavarini, M.; Caretta, A.; Mor, M.; Silva, C.; Impicciatore, M. Structural Analogues of Thioperamide: Pharmacological Evaluation of New Benzothiazole Derivatives at Peripheral Histamine Subtypes in Guinea-pigs. Pharm. Sci. 1995, 1, 177-180.
23. 3-Antagonists on Guinea-pig Isolated Preparation. Pharm. Sci. 1995, 1, 383-386.
24. Avdeef, A. pH-Metric log P. Part 1. Difference plots for Determining Ion-Pair Octanol-Water Partition Coefficients of Multiprotic Substances. Quant. Struct.-Act. Relat. 1992, 11, 510-517.
25. Baroni, M.; Clementi, S.; Cruciani, G.; Kettaneh-Wold, N.; Wold, S. D-Optimal Designs in QSAR. Quant. Struct.-Act. Relat. 1993, 12, 225-231.
26. Skagerberg, B.; Bonelli, D.; Clementi, S.; Cruciani, G.; Ebert, C. Principal Properties for Aromatic Substituents. A Multivariate Approach for Design in QSAR. Quant. Struct.-Act. Relat. 1989, 8, 32-38.
27. Box, G. E. P.; Hunter, W. G.; Hunter, J. S. Statistics for Experimenters; Wiley: New York, 1978; p 306.
28. DESDOP v. 2.0; MIA srl; Perugia, Italy.
29. Hansch, C.; Leo, A.; Hoekman, D. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants; American Chemical Society: Washington, DC, 1995.
30. 3-Receptors in Rat Cerebral Cortical Membranes. Br. J. Pharmacol. 1995, 114, 357-362.
31. 3 Receptor Models. Br. J. Pharmacol. 1994, 112, 1043-1048.
32. 3 Receptors in Mouse Brain Cortex and Guinea-Pig Ileum: Evidence for H3 Receptor Heterogeneity? Naunyn-Schmiedebergs Arch. Pharmacol. 1996, 353, 482-488.
33. 3 Receptor Heterogeneity? J. Pharmacol. Exp. Ther. 1996, 276, 1009-1015.
34. Norrington, F. E.; Hyde, R. M.; Williams, S. G.; Wootton, R. Physicochemical-Activity Relations in Practice. 1. A Rational Self-Consistent Data Bank. J. Med. Chem. 1975, 18, 604-607.
35. Austel, V.; Kutter, E.; Kalbfleisch, W. A New Easily Accessible Steric Parameter for Structure-Activity Relationships. Arzneim. Forsch. 1979, 29, 585-587.
36. Topliss, J. G.; Edwards, R. P. Chance Factors in Studies of Quantitative Structure-Activity Relationships. J. Med. Chem. 1979, 22, 1238-1244.
37. GOLPE v. 3.0.1, MIA srl, Perugia, Italy.
38. Baroni, M.; Costantino, G.; Cruciani, G.; Riganelli, D.; Valigi, R.; Clementi, S. Generating Optimal PLS Estimations (GOLPE): An Advanced Chemometric Tool for Handling 3D-QSAR Problems. Quant. Struct.-Act. Relat. 1993, 12, 9-20.
39. Norris, T.; McKee, R. L. 2-Guanidino-4(5)-p-chlorophenylimidazoles. J. Am. Chem. Soc. 1955, 77, 1056.
40. Grant, R. L.; Pyman, F. L. The Nitro- and Amino-derivatives of 4-Phenylglyoxaline J. Chem. Soc. 1921, 119, 1893-1903.
41. Snyder, H. R.; Elston, T. Polyphosphoric Acid as a Reagent in Organic Chemistry. VI. The Hydrolysis of Nitriles to Amides J. Am. Chem. Soc. 1954, 76, 3039-3040.
42. a Determination of Water-Insoluble Substances. Anal. Chem 1993, 65, 42-49.
43. Avdeef, A. pH-Metric log P. II: Refinement of Partition Coefficients and Ionization Constants of Multiprotic Substances. J. Pharm. Sci. 1993, 82, 1-8
44. 3-Receptor Ligands. Il Farmaco 1992, 47, 1343-1365.
45. Munson, P. J.; Rodbard, D. LIGAND: A Versatile Computerized Approach for Characterization of Ligand-Binding Systems. Anal. Biochem. 1980, 107, 220-239.
46. Sprague, E. D.; Larrabee, C. E., Jr.; Halsall, H. B. Statistical Evaluation of Alternative Models: Application to Ligand-Protein Binding. Anal. Biochem. 1980, 101, 175-181.
47. 3-Histamine Receptor Subtypes. Mol. Pharmacol. 1990, 38, 610-613.
48. 3 Histamine Receptor. J. Neurochem. 1990, 55, 1612-1616.
49. 3-Receptors in Guinea-Pig. Agents Actions 1993, 38, 158-164.