Conformational analysis of D1 dopamine receptor agonists: Pharmacophore assessment and receptor mapping

Journal of Medicinal Chemistry

Volumn 39, Issue 1, 1996, Pages 285-296

  Mottola, David M ^a   Laiter, Sergei ^b   Watts, Val J ^a   Tropsha, Alexander ^b   Wyrick, Steven D ^b   Nichols, David E ^c   Mailman, Richard B ^a,b  

^a UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

^b UNIVERSITY OF NORTH CAROLINA   (United States)

^c PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINOMETHYL 5,6 DIHYDROXY 3 PHENYLISOCHROMAN; 3 (1 ADAMANTYL) 1 AMINOMETHYL 3,4 DIHYDRO 5,6 DIHYDROXY 1H 2 BENZOPYRAN; 3 ALLYL 6 CHLORO 2,3,4,5 TETRAHYDRO 7,8 DIHYDROXY 1 PHENYL 1H 3 BENZAZEPINE; ADENYLATE CYCLASE; CATECHOL; DIHYDREXIDINE; DOPAMINE; DOPAMINE 1 RECEPTOR; DOPAMINE 1 RECEPTOR STIMULATING AGENT; DRUG CARRIER; HYDROXYL GROUP; NITROGEN; SKF 89626; DOPAMINE RECEPTOR STIMULATING AGENT; LIGAND; PHENANTHRIDINE DERIVATIVE;

ANIMAL TISSUE; ARTICLE; BINDING SITE; CALCULATION; CONFORMATION; ENERGY; ENZYME ACTIVITY; MODEL; NONHUMAN; RAT; RECEPTOR BINDING; ANIMAL; BRAIN; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER PROGRAM; COMPUTER SIMULATION; DRUG EFFECT; DRUG POTENTIATION; METABOLISM; STRUCTURE ACTIVITY RELATION;

ADENYLATE CYCLASE; ANIMALS; BRAIN; COMPUTER SIMULATION; DOPAMINE; DOPAMINE AGONISTS; LIGANDS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PHENANTHRIDINES; RATS; RECEPTORS, DOPAMINE D1; SOFTWARE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0029664313     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9502100     Document Type: Article

References (47)

1. 1 dopamine receptor. Nature 1990, 347, 72-76.
2. 1 dopamine receptors. Nature 1990, 347, 76-80.
3. 1 receptor encoded by intronless gene on chromosome 5. Nature 1990, 347, 80-83.
4. 1 dopamine receptor linked to adenylate cyclase activation. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 6273-6727.
5. 1a receptor. Proc. Natl. Acad. Sci. U.S.A 1991, 88, 7491-7495.
6. 1. Nature 1991, 250, 614-618.
7. 2 dopamine receptor classification and its functional implications. Synapse 1987, 1, 347-388.
8. 2 behavioral actions. Eur. J. Pharmacol. 1984, 101, 159-160.
9. Christensen, A. V.; Arnt, J.; Hyttel, J.; Larsen, J. J.; Svendsen, O. Pharmacological effects of a specific dopamine D-1 antagonist SCH23390 in comparison with neuroleptics. Life Sci. 1984, 34, 1529-1540.
10. 1 receptor agonist. Eur. J. Pharmacol. 1989, 166, 111-113.
11. 1 full agonist. J. Med. Chem. 1990, 33, 1756-1764.
12. 1 dopamine receptor agonist. J. Pharmacol. Exp. Ther. 1992, 262, 383-393.
13. 1 dopamine receptor agonist. Neuropsychopharmacology 1991, 5, 187-195.
14. 1 agonist, reduces MPTP-induced parkinsonism in African green monkeys. Eur. J. Pharmacol. 1991, 199, 387-388.
15. 2 dopamine receptors independently regulate spontaneous blink rate in the Vervet monkey. J. Pharmacol. Exp. Ther. 1991, 255, 595-600.
16. 1 receptors. J. Neurochem. 1991, 57, 1563-1569.
17. Cannon, J. G. Chemistry of Dopaminergic Agonists. In Advances in Neurology; (Calne, D. B., Chase, T. N., Barbeau, A., Eds.; Raven Press: New York, 1975, Vol. 9, pp 177-183.
18. McDermed, J. D.; Freeman, H. S.; Ferris, R. M. Enantioselectivity in the binding of (+) and (-)-2-amino-6, 7-dihydroxy-1,2,3,4-tetrahydronapthalene and related agonists to dopamine receptors. In Catecholamines: Basic and Clinical Frontiers; Usdin, E., Kopin, I. J., Barchas, J., Eds.; Pergamon Press: New York, 1978; pp 568-570.
19. Nichols, D. E. The development of novel dopamine agonists. In Dopamine Receptors; Kaiser, C., Kebabian, J. W., Eds.; ACS Symposium Series 224; American Chemical Society: Washington, DC, 1983; pp 201-218.
20. Truex, L. L.; Foreman, M. M.; Riggs, R. M.; Nichols, D. E. Effects of modifications of the 4-(3, 4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline structure on dopamine sensitive rat retinal adenylate cyclase activity. Soc. Neurosci. Abstr. 1985, 11, 315.
21. 1 receptor agonists. Eur. J. Pharmacol. 1987, 137, 291-292.
22. Charifson, P. S.; Wyrick, S. D.; Hoffman, A. J.; Ademe Simmons, R. M.; McDougald, D. M.; Mailman, R. B. Synthesis and pharmacological characterization of 1-phenyl, 4-phenyl and 1-benzyl-1,2,3,4-tetrahydroisoquinolines as dopamine receptor ligands. J. Med. Chem. 1988, 31, 1941-1946.
23. 1 dopamine receptor ligands. J. Med. Chem. 1989, 32, 2050-2058.
24. Weinstock, J.; Oh, H.-J.; DeBrosse, C. W.; Egglestone, D. S.; Wise, M.; Flaim, K. E.; Gessner, G. W.; Sawyer, J. L.; Kaiser, C. Synthesis, conformation, and dopaminergic activity of 5,6-ethano-bridged derivatives of selective dopaminergic 3-benzazepines. J. Med. Chem. 1987, 30, 1303-1308.
25. 1 selective ligand (5R)-8-Chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepin-7-ol. J. Med. Chem. 1989, 32, 1913-1921.
26. Petersson, I.; Liljefors, T.; Bogeso, K. Conformationl analysis and Structure-Activity relationships of selective dopamine D-1 receptor agonists and antagonists of the benzazepine series. J. Med. Chem. 1990, 33, 2197-2204.
27. 1-selective benzazepines. J. Comput. Chem. 1993, 14, 571-578.
28. 1 receptor by agonists. J. Comput.-Aided Mol. Des. 1993, 7, 659-670.
29. 2 agonists. J. Mol. Mod. 1995, 1 (electronic publication).
30. Marshall, G. R.; Barry, C. D.; Bosshard, H. E.; Dammkoehler, R. A.; Dunn, D. A. The Conformational Parameter in Drug Design: the Active Analog Approach. ACS Symp. Ser. 1979, 112, 205-226.
31. Wyrick, S. D.; Mailman, R. B. Tritium labeled (+)-7-chloro-8-hydroxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benza zepine (SCH23390). J. Labelled Compd. Radiopharm. 1983, 22, 189-195.
32. Brewster, W. K. Studies directed toward the synthesis of certain trans-fused benzo[a]phenanthridines as structurally rigid dopamine D-1 agonists and antagonists. Dissertation, Purdue University, 1990.
33. Heffner, T. G.; Hartman, J. A.; Seiden, L. S. A rapid method for the regional dissection of the rat brain. Pharmacol. Biochem. Behav. 1980, 13, 453-456.
34. 1-like dopamine receptor. J. Neurochem. 1985, 45, 1601-1611.
35. Lowry, O. H.; Rosebrough, N. J.; Farr, A. L.; Randall, R. J. Protein measurement with the folin phenol reagent. J. Biol. Chem. 1951, 193, 265-275.
36. Schulz, D. W.; Mailman, R. B. An improved, automated adenylate cyclase assay utilizing preparative HPLC: effects of phosphodiesterase inhibitors. J. Neurochem. 1984, 42, 764-774.
37. 1 agonist. J. Med. Chem. 1990, 33, 2948-2950.
38. 1 agonist. J. Med. Chem. 1990, 33, 2948-2950.
39. 1 receptor. Eur. J. Pharmacol. 1991, 199, 209-219.
40. 1 dopamine receptor agonists: the role of spare receptors. Synapse 1995, 21, 177-187.
41. Kaiser, C.; Dandridge, P. A.; Garvey, E.; Hahn, R. A.; Sarau, H. M.; Setler, P. E.; Bass, L. S.; Clardy, J. Absolute stereochemistry and dopaminergic activity of enantiomers of 2,3,4,5-tetrahydro-7,8-dihydroxy-1-phenyl-1H-3-benzazepine. J. Med. Chem. 1982, 25, 697-703.
42. Dandridge, P. A.; Kaiser, C.; Brenner, M.; Gaitanopoulos, D.; Davis, L. D.; Webb, R. L.; Foley, J. J.; Sarau, H. M. Synthesis, resolution, absolute stereochemistry, and enantioselectivity of 3′,4′-dihydroxynomifensine. J. Med. Chem. 1984, 27, 28-35.
43. 1 dopamine receptor agonist. J. Med. Chem. 1994, 37, 2453-2460.
44. 1 dopamine receptor. Neuropharmacology 1989, 28, 401-405.
45. 1 Receptors; Breese, G. R., Creese, I., Eds.; Plenum Press: New York, 1986; pp 53-72.
46. 1 receptor agonists lacking a catechol group. J. Med. Chem. 1991, 34, 303-307.
47. 2 dopamine receptor. Trends Neurosci. 1990, 9, 373-378.