Design, synthesis, and evaluation of potent and selective ligands for the dopamine 3 (D3) receptor with a novel in vivo behavioral profile

Journal of Medicinal Chemistry

Volumn 51, Issue 19, 2008, Pages 5905-5908

  Chen, Jianyong ^a   Collins, Gregory T ^a   Zhang, Jian ^a   Yang, Chao Yie ^a   Levant, Beth ^c   Woods, James ^a   Wang, Shaomeng ^a,b  

^a UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

^b UNIVERSITY OF MICHIGAN   (United States)

^c UNIVERSITY OF KANSAS SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CJ 1037; CJ 703; CJ 998; DOPAMINE 3 RECEPTOR; DOPAMINE 3 RECEPTOR STIMULATING AGENT; PRAMIPEXOLE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; IN VIVO STUDY; NONHUMAN; RAT;

ANIMALS; BEHAVIOR, ANIMAL; BENZOTHIAZOLES; BINDING SITES; BINDING, COMPETITIVE; DOPAMINE AGONISTS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; HUMANS; HYDROGEN BONDING; HYPOTHERMIA; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; RATS; RECEPTORS, DOPAMINE D1; RECEPTORS, DOPAMINE D2; RECEPTORS, DOPAMINE D3; SENSITIVITY AND SPECIFICITY; SOLUBILITY; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; YAWNING;

EID: 53549083831     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm800471h     Document Type: Article

References (34)

1. 3 receptor as a therapeutic target for antipsychotic and antiparkinsonian drugs. Pharmacol. Ther. 2001, 90, 231-259.
2. 3 receptor agonist. Nature 1999, 400, 371-375.
3. Koob, G. F.; Caine, S. B. Cocaine addition therapy: Are we partially there? Nat. Med. 1999, 5, 993-995.
4. Montplaisir, J.; Nicolas, A.; Denesle, R.; Gomez-Mancilla, B. Restless legs syndrome improved by pramipexole: a double-blind randomized trial. Neurology 1999, 52, 938-943.
5. 3 dopamine receptor, neurobiology and potential clinical relevance. Pharmacol. Rev. 1997, 49, 231-252.
6. 3 Receptor Partial Agonists and Antagonists as Potential Drug Abuse Therapeutic Agents. J. Med. Chem. 2005, 48, 3663-3679.
7. 3 Receptor Ligands: Potential Substance Abuse Therapeutic Agents. J. Med. Chem. 2007, 50, 4135-4146.
8. 2 agonists. J. Med. Chem. 1994, 37, 4251-4257.
9. Wustrow, D.; Belliotti, T.; Glase, S.; Kesten, S. R.; Johnson, D.; Colbry, N.; Rubin, R.; Blackburn, A.; Akunne, H.; Corbin, A.; Davis, M. D.; Georgic, L.; Whetzel, S.; Zoski, K.; Heffner, T.; Pugsley, T.; Wise, L. Aminopyrimidines with high affinity for both serotonin and dopamine receptors. J. Med. Chem. 1998, 41, 760-771.
10. 3 dopamine receptor ligands. Bioorg. Med. Chem. Lett. 1997, 7, 2403-2408.
11. 3 receptor subtype. J. Med. Chem. 2001, 44, 3175-3186.
12. 3 receptor antagonists and partial agonists. J. Med. Chem. 2002, 45, 4594-4597.
13. 3 receptor ligands. J. Med. Chem. 2003, 46, 3883-3899.
14. 3 receptor ligands. J. Med. Chem. 2002, 45, 5727-5735.
15. 2 receptors. J. Med. Chem. 2003, 46, 3822-3839.
16. Campiani, G.; Butini, S.; Fattorusso, C.; Catalanotti, B.; Gemma, S.; Nacci, V.; Morelli, E.; Cagnotto, A.; Mereghetti, I.; Mennini, T.; Carli, M.; Minetti, P.; Di Cesare, M. A.; Mastroianni, D.; Scafetta, N.; Galletti, B.; Stasi, M. A.; Castorina, M.; Pacifici, L.; Vertechy, M.; Serio, S. D.; Ghirardi, O.; Tinti, O.; Carminati, P. Pyrrolo[1,3]benzothiazepine-based serotonin and dopamine receptor antagonists: molecular modeling, further structure-activity relationship studies, and identification of novel atypical antipsychotic agents. J. Med. Chem. 2004, 47, 143-157.
17. 3 Receptor. J. Med. Chem. 2005, 48, 839-848.
18. 3 ligands through a hybrid pharmacophore- and structure-based database searching approach. J. Med. Chem. 2003, 46, 4377-4392.
19. 3 receptor antagonists. 1. Synthesis and structure-activity relationship of 5,6-dimethoxyl-N-alkyl- and N-alkylaryl-substituted 2-aminoindans. J. Med. Chem. 2001, 44, 4716-4732.
20. 3) ligands. Bioorg. Med. Chem. Lett. 2005, 15, 1701-1705.
21. Ding, K.; Chen, J.; Ji, M.; Wu, X.; Varady, J.; Yang, C.; Lu, Y.; Deschamps, J. R.; Levant, B.; Wang, S. Enantiomerically Pure Hexahydropyrazinoquinolines as Potent and Selective Dopamine 3 Subtype Receptor Ligands. J. Med. Chem. 2005, 48, 3171-3181.
22. 3 Receptor Ligands with Improved Solubility. Bioorg. Med. Chem. Lett. 2006, 16, 443-146.
23. Millan, M. J.; Maiofiss, L.; Cussac, D.; Audinot, V.; Boutin, J. A.; Newman-Tancredi, A. Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. I. A multivariate analysis of the binding profiles of 14 drugs at 21 native and cloned human receptor subtypes. J. Pharmacol. Exp. Ther. 2002, 303, 791-804.
24. 3 receptor-mediated behavior. J. Pharmacol. Exp. Ther. 2005, 314, 310-319.
25. 2 agonists and antagonists. Psychopharmacology (Berlin) 2007, 193, 159-170.
26. Cherezov, V.; Rosenbaum, D. M.; Hanson, M. A.; Rasmussen, S. G.; Thian, F. S.; Kobilka, T. S.; Choi, H. J.; Kuhn, P.; Weis, W. I.; Kobilka, B. K.; Stevens, R. C. High resolution crystal structure of an engineered human beta2-adrenergic G protein-coupled receptor. Science 2007, 318, 1258-1265.
27. Rasmussen, S. G.; Choi, H. J.; Rosenbaum, D. M.; Kobilka, T. S.; Thian, F. S.; Edwards, P. C.; Burghammer, M.; Ratnala, V. R.; Sanishvili, R.; Fischetti, R. F.; Schertler, G. F.; Weis, W. I.; Kobilka, B. K. Crystal structure of the human beta2 adrenergic G-protein-coupled receptor. Nature 2007, 450, 383-387.
28. Kenakin, T. The classification of seven transmembrane receptors in recombinant expression systems. Pharmacol. Rev. 1996, 48, 413-463.
29. 2-like dopamine receptors in rat brain. J. Pharmacol. Exp. Ther. 1992, 262, 929-935.
30. 3 dopamine receptor, in rat brain: a receptor binding and quantitative autoradiographic study. Neuropsychopharmacology 1998, 18, 305-316.
31. Levant, B. Characterization of dopamine receptors. In Current Protocols in Pharmacology; Enna, S. J.; Williams, M., Ferkany, J. W., Kenakin, T., Porsolt, R. D., Sullivan, J. P., Eds.; John Wiley & Sons: New York, 1998, pp 1.6.1-1.6.16.
32. 3 receptor agonists. Neuropharmacology 1999, 38, 1389-1396.
33. 4 receptors. Neuropharmacology. 2003, 44, 1047-1053.
34. Fujikawa, M.; Nagashima, M.; Inoue, T.; Yamada, K.; Furukawa, T. Partial agonistic effects of OPC-14597, a potential antipsychotic agent, on yawning behavior in rats. Pharmacol., Biochem. Behav. 1996, 53, 903-909.