Azole endothelin antagonists. 1. A receptor model explains an unusual structure-activity profile

Journal of Medicinal Chemistry

Volumn 39, Issue 4, 1996, Pages 957-967

  Von Geldern, Thomas W ^a   Hutchins, Charles ^a,b   Kester, Jeffrey A ^a   Wu Wong, Jinshyun R ^a   Chiou, William ^a   Dixon, Douglas B ^a   Opgenorth, Terry J ^a  

^a ABBOTT LABORATORIES   (United States)

^b Structural Biology Department

Author keywords

[No Author keywords available]

Indexed keywords

2 [[2 [[2 [[(HEXAHYDRO 1H AZEPIN 1 YL)CARBONYL]AMINO] 4 METHYLPENTANOYL]AMINO] 3 (1 METHYL 1H INDOL 3 YL)PROPIONYL]AMINO] 3 (2 PYRIDYL)PROPIONIC ACID; CYCLO(DEXTRO TRYPTOPHYL DEXTRO ASPARTYLPROLYL DEXTRO VALYLLEUCYL); ENDOTHELIN RECEPTOR ANTAGONIST; PYRROLE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BLOOD VESSEL FUNCTION; CONTROLLED STUDY; DRUG EFFECT; DRUG SYNTHESIS; ENDOTHELIUM CELL; INTRADUODENAL DRUG ADMINISTRATION; LIGAND BINDING; NONHUMAN; RAT; REACTION ANALYSIS; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION; VASCULAR SMOOTH MUSCLE;

EID: 0030062528     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950591h     Document Type: Article

References (29)

1. Yanagisawa, M.; Kurihara, H.; Kimura, S.; Tomobe, Y.; Kobayashi, M.; Mitsui, Y.; Yazaki, Y.; Goto, K.; Masaki, T. A Novel Potent Vasoconstrictor Peptide Produced by Vascular Endothelial Cells. Nature 1988, 332, 411-415.
2. (a) Opgenorth, T. J. Endothelin Receptor Antagonism. Adv. Pharmacol. 1995, in press.
3. (b) Mattoli, S.; Soloperto, M.; Marini, M.; Fasoli, A. Levels of Endothelin in the Bronchoalveolar Lavage Fluid of Patients with Symptomatic Asthma and Reversible Airflow Obstruction. J. Allergy Clin. Immunol. 1991, 88, 376-384.
4. (c) Golfman, L.; Hata, T.; Beamish, R.; Dhall, N. Role of Endothelin in Heart Function and Disease. Can. J. Cardiol. 1993, 9, 635-653.
5. (d) Li, H.; Elton, T.; Chen, Y.; Oparil, S. Increased Endothelin Receptor Gene Expression in Hypoxic Rat Lung. Am. J. Physiol. 1994, 266, L553-L560.
6. (e) Ohlstein, E.; Douglas, S. Endothelin-1 Modulates Vascular Smooth Muscle Structure and Vasomotion: Implications in Cardiovascular Pathology. Drug Dev. Res. 1993, 29, 108-128.
7. (f) Alberts, G.; Peifley, K.; Johns, A.; Kleha, J.; Winkles, J. Constitutive Endothelin-1 Overexpression Promotes Smooth Muscle Cell Proliferation via an External Autocrine Loop. J. Biol. Chem. 1994, 269, 10112-10118.
8. Sakurai, T.; Yanagisawa, M.; Masaki, T. Molecular characterization of endothelin receptors. Trends Pharmacol. Sci. 1992, 13, 103-108. Masaki, T.; Vane, J. R.; Vanhoutte, P. M.; V. International Union of Pharmacology Nomenclature of Endothelin Receptors. Pharmacol. Rev. 1994, 46, 137-142.
9. Sakurai, T.; Yanagisawa, M.; Masaki, T. Molecular characterization of endothelin receptors. Trends Pharmacol. Sci. 1992, 13, 103-108. Masaki, T.; Vane, J. R.; Vanhoutte, P. M.; V. International Union of Pharmacology Nomenclature of Endothelin Receptors. Pharmacol. Rev. 1994, 46, 137-142.
10. A Selectivity. Potency-and Solubility-Enhancing Modifications. J. Med. Chem. 1992, 35, 2139-2142.
11. A Receptor Antagonist, BQ-485, and its Preventive Effect on Experimental Cerebral Vasospasm in Dogs. Biochem. Biophys. Res. Commun. 1993, 195, 969-975. Ishikawa, K.; Fukami, T.; Hayama, T.; Niiyama, K.; Nagase, T.; Mase, T.; Fujita, K.; Ihara, M.; Ikemoto, F.; Yano, M. Endothelin antagonistic peptide derivatives. EP 460679, 1991.
12. A Receptor Antagonist, BQ-485, and its Preventive Effect on Experimental Cerebral Vasospasm in Dogs. Biochem. Biophys. Res. Commun. 1993, 195, 969-975. Ishikawa, K.; Fukami, T.; Hayama, T.; Niiyama, K.; Nagase, T.; Mase, T.; Fujita, K.; Ihara, M.; Ikemoto, F.; Yano, M. Endothelin antagonistic peptide derivatives. EP 460679, 1991.
13. (c) Aramori, I.; Nirei, H.; Shoubo, M.; Sogabe, K.; Nakamura, K.; Kojo, H.; Notsu, Y.; Ono, T.; Nakanishi, S. Subtype Selectivity of a Novel Endothelin Antagonist FR-139317 for the Two Endothelin Receptors in Transfected Chinese Hamster Ovary Cells. Mol. Pharmacol. 1993, 43, 127-131. Hemmi, K.; Neya, M.; Fukami, N.; Hashimoto, M.; Tanaka, H.; Kayakiri, N. New Endothelin Antagonists and Their Preparation. WO 93/10144, 1993.
14. (c) Aramori, I.; Nirei, H.; Shoubo, M.; Sogabe, K.; Nakamura, K.; Kojo, H.; Notsu, Y.; Ono, T.; Nakanishi, S. Subtype Selectivity of a Novel Endothelin Antagonist FR-139317 for the Two Endothelin Receptors in Transfected Chinese Hamster Ovary Cells. Mol. Pharmacol. 1993, 43, 127-131. Hemmi, K.; Neya, M.; Fukami, N.; Hashimoto, M.; Tanaka, H.; Kayakiri, N. New Endothelin Antagonists and Their Preparation. WO 93/10144, 1993.
15. (d) Mihara, S. I.; Nakajima, S.; Matumura, S; Kohnoike, T.; Fujimoto, M. Pharmacological Characterization of a Potent Nonpeptide Endothelin Receptor Antagonist, 97-139. J. Pharmacol. Exp. Ther. 1994, 268, 1122-1128.
16. A Antagonist 5-(Dimethylamino)-N-(3,4-dimethyl-5-isoxarolyl)- 1-naphthalenesulfonamide. J. Med. Chem. 1994, 37, 329-331.
17. (f) Clozel, M.; Breu, V.; Gray, G. A.; Kalina, B.; Loffler, B. M.; Burri, K.; Cassal, J. M.; Hirth, G.; Muuler, M.; Neidhart, W.; Ramuz, H. Pharmacological Characterization of Bosentan, a New Potent Orally Active Non-peptide Endothelin Receptor Antagonist. J. Pharmacol. Exp. Ther. 1994, 270, 228-235.
18. (g) Ohlstein, E. H.; Nambi, P.; Douglas, S. A.; Edwards, R. M.; Gellai, M.; Lago, M. A.; Leber, J. D.; Cousins, R. D.; Gao, A.; Frazee, J. S.; Peishoff, C. E.; Bean, J. W.; Eggleston, D. S.; Elshourbagy, N. A.; Kumar, C.; Lee, J. A.; Yu, T.-L.; Louden, C.; Brooks, D. P.; Weinstock, J.; Feuerstein, G.; Poste, G.; Ruffolo, R. R., Jr.; Gleason, J. G.; Elliott, J. D. SB 209670, a Rationally Designed Potent Nonpeptide Endothelin Receptor Antagonist. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 8052-8056.
19. (h) Greenlee, W. J.; Walsh, T. F.; Pettibone, D. J.; Tata, J. R.; Rivero, R. A.; Williams, D. L.; Bagley, S. W.; Dhanoa, D. S.; Chakravarty, P. K.; Fitch, K. J.; Broten, T. P.; Kevin, N. J. Phenoxyphenylacetic Acid Derivatives. WO 94/ 21590, 1994.
20. A) Receptor-Selective Antagonists. J. Med. Chem. 1995, 38, 1259-1263.
21. Gordon, T. D.; Singh, J.; Hansen, P. E.; Morgan, B. A. Synthetic Approaches to the 'Azole' Peptide Mimetics. Tetrahedron Lett. 1993, 34, 1901-1904.
22. Hutchins, C. Three-dimensional Models of the D1 and D2 Dopamine Receptors. Endocrine J. 1994, 2, 7-23.
23. Henderson, R.; Baldwin, J.; Ceska, T. H.; Zemlin, F.; Beckmann, E.; Downing, K. Model for the Structure of Bacteriorhodopsin Based on High-resolution Electron Cryo-microscopy. J. Mol. Biol. 1990, 213, 899-929.
24. Kyte, J.; Doolittle, R. F. A Simple Method for Displaying the Hydropathic Character of a Protein. J. Mol. Biol. 1982, 157, 105-132.
25. Elshourbagy, N. A.; Korman, D. R.; Wu, H.-L.; Sylvester, P. R.; Lee, J. A.; Nuthalaganti, P.; Bergsma, D. O.; Kumar, C. S.; Nambi, P. Molecular Characterization and Regulation of the Human Endothelin Receptors. J. Biol. Chem. 1993, 268, 3873-3879.
26. B Receptor Subtype-selective Ligand Binding While Abolishing Phospholipase C Activation in Both Receptors. FEBS Lett. 1995, 361, 243-249.
27. Eisenberg, D.; McLachlan, A. D. Solvation Energy in Protein Folding and Binding. Nature 1986, 319, 199-203.
28. (a) Wesson, L.; Eisenberg, D. Atomic Solvation Parameters Applied to Molecular Dynamics of Proteins in Solution. Protein Sci. 1992, 1, 227-235.
29. Sharp, K. A,; Nicholls, A.; Friedman, R.; Honig, B. Extracting Hydrophobic Free Energies from Experimental Data: Relationship to Protein Folding and Theoretical Models. Biochemistry 1991, 30, 9686-9697.