Affinity for dopamine D2, D3, and D4 receptors of 2-aminotetralins. Relevance of D2 agonist binding for determination of receptor subtype selectivity

Journal of Medicinal Chemistry

Volumn 39, Issue 21, 1996, Pages 4233-4237

  Van Vliet, L Alexander ^a   Tepper, Pieter G ^a   Dijkstra, Durk ^a   Damsma, Geert ^a   Wikström, Håkan ^a   Pugsley, Thomas A ^b   Akunne, Hyacinth C ^b   Heffner, Thomas G ^b   Glase, Shelly A ^b   Wise, Lawrence D ^b  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOTETRALIN DERIVATIVE; DOPAMINE 2 RECEPTOR; DOPAMINE 2 RECEPTOR STIMULATING AGENT; DOPAMINE 3 RECEPTOR; DOPAMINE 4 RECEPTOR; 2 AMINOTETRALIN; 2-AMINOTETRALIN; DRD3 PROTEIN, HUMAN; DRD4 PROTEIN, HUMAN; TETRALIN DERIVATIVE;

ANIMAL CELL; ARTICLE; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; RECEPTOR AFFINITY; ANIMAL; CELL LINE; CHEMISTRY; CRICETULUS; DRUG POTENTIATION; ENZYME SPECIFICITY; FEMALE; HAMSTER; HUMAN; KINETICS; METABOLISM; OVARY;

ANIMALS; CELL LINE; CRICETINAE; CRICETULUS; FEMALE; HUMANS; KINETICS; OVARY; RECEPTORS, DOPAMINE D2; RECEPTORS, DOPAMINE D3; RECEPTORS, DOPAMINE D4; SUBSTRATE SPECIFICITY; TETRAHYDRONAPHTHALENES;

EID: 0006188075     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960345l     Document Type: Article

References (41)

1. (a) Bamberger, E.; Müller, R. Über β-Tetrahydronaphtylamin. Ber. 1888, 21, 1112-1125.
2. (b) Kraushaar, A. Pharmakologische Untersuchungen von Modellsubstanzen für die Lysergsäure. (Pharmacological Investigations of Model Substances of Lysergic Acid.) Arzneim. Forsch. 1954, 4, 273-277.
3. (c) Violland, R.; Violland-Duperret, N.; Pacheco, H.; Trouiller, G.; Leblanc, A. VIII. Psychotropes potentiels. Synthèse et Activité Pharmacologique d'Amino-2-tétralines Apparentées à Divers Psychotomimétiques. (Potential Psychotropics. Synthesis and Pharmacological Activity of 2-Aminotetralins Related to Various Psychotomimetics.) Chim. Ther. 1971, 3, 196-202.
4. Cannon, J. G.; Kim, J. C.; Aleem, Mohd. A.; Long, J. P. Centrally Acting Emetics. 6. Derivatives of β-Naphthylamine and 2-Indanamine. J. Med. Chem. 1972, 15, 348-350.
5. Arvidsson, L.-E.; Hacksell, U.; Nilsson, J. L.; Hjorth, S.; Carlsson, A.; Lindberg, P.; Sanchez, D.; Wikström, H. 8-Hydroxy-2-(di-n-propylamino)tetralin, a New Centrally Acting 5-Hydroxytryptamine Receptor Agonist. J. Med. Chem. 1981, 24, 921-923.
6. Copinga, S.; Tepper, P. G.; Grol, C. J.; Horn, A. S.; Dubocovich, M. L. 2-Amido-8-Methoxytetralins: A Series of Nonindolic Melatonin-like Agents. J. Med. Chem. 1993, 36, 2891-2898.
7. McDermed, J. D.; McKenzie, G. M.; Freeman, H. S. Synthesis and Dopaminergic Activity of (±)-, (+)-, and (-)- 2-Dipropylamino-5-hydroxy-1,2,3,4-tetrahydronaphthalene. J. Med. Chem. 1976, 19, 547-549.
8. Cannon, J. G.; Lee, T.; Goldman, H. D.; Costall, B.; Naylor, R. J. Cerebral Dopamine Agonist Properties of Some 2-Amino-tetralin Derivatives after Peripheral and Intracerebral Administration J. Med. Chem. 1977, 20, 1111-1116.
9. Seiler, M. P.; Markstein, R. Further Characterization of Structural Requirements for Agonists at the Striatal Dopamine D-1 Receptor. Mol. Pharmacol. 1982, 22, 281-289.
10. Hacksell, U.; Svensson, U.; Nilsson, J. L. G.; Hjorth, S.; Carlsson, A,; Wikström, H.; Lindberg, P.; Sanchez, D. N-Alkylated 2-Aminotetralins: Central Dopamine-Receptor Stimulating Activity. J. Med. Chem. 1979, 22, 1469-1475.
11. Seiler, M. P.; Stoll A. P.; Closse, A.; Frick, W.; Jaton, A.; Vigouret, J.-M. Structure-Activity Relationships of Dopaminergic 5-Hydroxy-2-aminotetralin Derivatives with Functionalized N-Alkyl Substituents. J. Med. Chem. 1986, 29, 912-917.
12. Wikström, H.; Andersson, B.; Sanchez, D.; Lindberg, P.; Arvidsson, L.-E.; Johansson, A. M.; Nilsson, J. L. G.; Svensson, K.; Hjorth, S.; Carlsson, A. Resolved Monophenolic 2-Aminotetralins and 1,2,3,4,4a,5,6,10b-Octahydrobenzo[f]quinolines: Structural and Stereochemical Considerations for Centrally Acting Pre- and Postsynaptic Dopamine-Receptor Agonists. J. Med. Chem. 1985, 28, 215-225.
13. 2 Dopamine Receptor Agonist. Pharm. Weekbl., Sci. Ed. 1985, 7, 208-211.
14. 1 Receptor. Mol. Pharmacol. 1984, 26, 452-457.
15. 3H]-7-hydroxy-N,N-din-propyl-2-aminotetralin. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 8155-8159.
16. 3 Receptor Ligand. Eur. J. Pharmacol. 1993, 249, R9-R10.
17. 3) as a Target for Neuroleptics. Nature 1990, 347, 146-151.
18. Van Tol, H. H.; Bunzow, J. R.; Guan, H. C.; Sunahara, R. K.; Seeman, P; Niznik, H. B.; Civelli, O. Cloning of the Gene for a Human Dopamine D4 Receptor with High Affinity for the Antipsychotic Clozapine. Nature 1991, 350, 610-614.
19. 4 Receptors Elevated in Schizophrenia. Nature 1993, 365, 441-445.
20. 125I]Epidepride. Eur. J. Pharmacol. 1995, 286, R3-R5.
21. 4 Receptors Increased in Schizophrenia? J. Neurochem. 1994, 63, 1576-1577.
22. 4 Receptors in Drug-treated Schizophrenia. Eur. J. Pharmacol. 1995, R5-R6.
23. 3 Receptor Agonist Ligand, to CHO-K1 Cells. Life Sci. 1995, 57, 1401-1410.
24. 3 Agonist PD 128907. J. Pharmacol. Exp. Ther. 1995, 275, 1355-1366.
25. Cornforth, J. W.; Cornforth, R. H.; Robinson, R. The Preparation of β-Tetralone From β-Naphtol and Some Analogous Transformations. J Chem. Soc. 1942, 689-691.
26. (a) Sibley, D. R.; Delean, A.; Creese, I. Anterior Pituitary Dopamine Receptors: Demonstration of Interconvertible High an Low Affinity States of the D2 Dopamine Receptor. J. Biol. Chem. 1982, 257, 6351-6361.
27. 3H-2-Amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphthalene, as High Agonist Affinity States of the D1 and D2 Dopamine Receptors, Respectively. J. Neurochem. 1986, 46, 1058-1067.
28. (c) Seeman, P.; Watanabe, M.; Grigoriadis, D.; Tedesco, J. L.; George, S. R.; Svensson, U.; Nilsson, J. L. G.; Neumeyer, J. L. Dopamine D-2 Receptor Binding Sites for Agonists: A Tetrahedral Model. Mol. Pharmacol. 1985, 28, 391-399.
29. (d) Hamblin, M. W.; Leff, S. E.; Creese, I. Interactions of Agonists with D2 Dopamine Receptors: Evidence for a Single Receptor Population Existing in Multiple Agonist Affinity-States in Rat Striatal Membranes. Biochem. Pharmacol. 1984, 33, 877-887.
30. (a) Chio, C. L.; Lajiness, M. E.; Huff, R. M.; Activation of Heterologously Expressed D3 Dopamine Receptors: Comparison with D2 Dopamine Receptors. Mol. Pharmacol. 1994, 45, 51-60.
31. 125I](R)-Trans-7-hydroxy-2-[N-propyl-N-(3′-iodo-2′- propenyl)amino]tetralin Binding to Dopamine D3 Receptors in Rat Olfactory Tubercle. J. Pharmacol. Exp. Ther. 1994, 268, 935-942.
32. Chen, C.; Okayama, H. High-efficiency Transformation of Mammalian Cells by Plasmid DNA. Mol. Cell Biol. 1987, 7, 2745-2752.
33. 3 Receptor Expressed in Transfected Cell Lines. Eur. J. Pharmacol., Mol. Pharmacol. Sect. 1994, 266, 79-85.
34. 4.2 Receptor in CHO K1 Cells. Soc. Neurosci. 1995, 21, 620.
35. 2L Chimeras (COS-7 Cells). Methods Findings Exp. Clin. Pharmacol. (submitted for publication).
36. 50) of an Enzymatic Reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
37. 2-Selective Agonist N-0437. Naunyn-Schmiedeberg's Arch, Pharmacol. 1991, 343, 134-142.
38. Horn, A. S. U.S. Patent No. 4,564,628, January 14, 1986.
39. Ames, D. E.; Evans, D.; Grey, T. F.; Islip, P. J.; Richards, K. E. The Synthesis of Alkoxy-1,2,3,4-tetrahydronaphthalene Derivatives. Part I. 2-Amino-, Alkylamino-, and Dialkylamino-derivatives. J. Chem. Soc. 1965, 2636-2641.
40. Windaus, A. Über einige Derivate des ac.-Tetrahydro-β-naphtylamins. (About Some Derivatives of Acetyl-tetrahydro-β-naphthylamine.) Ber. 1924, 57, 1731-1739.
41. 2 Dopamine Agonists. Naunyn-Schmiedeberg's Arch. Pharmacol. 1987, 336, 487-493.