N-(ω)-(4-(2-methoxyphenyl)piperazin-1-yl)alkyl)carboxamides as dopamine D2 and D3 receptor ligands

Journal of Medicinal Chemistry

Volumn 46, Issue 18, 2003, Pages 3883-3899

  Hackling, Anneke ^a   Ghosh, Robin ^b   Perachon, Sylvie ^c   Mann, André ^d   Höltje, Hans Dieter ^b   Wermuth, Camille G ^d   Schwartz, Jean Charles ^e   Sippl, Wolfgang ^b   Sokoloff, Pierre ^e   Stark, Holger ^a  

^a GOETHE UNIVERSITY   (Germany)

^b HEINRICH HEINE UNIVERSITY   (Germany)

^c Laboratoire Bioprojet   (France)

^d UNIVERSITÉ DE STRASBOURG   (France)

^e CENTRE PAUL BROCA   (France)

Author keywords

[No Author keywords available]

Indexed keywords

4 IODO N [4 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]BUTYL]CINNAMOYLAMIDE; ACRYLAMIDE DERIVATIVE; BP 897; DOPAMINE 2 RECEPTOR; DOPAMINE 3 RECEPTOR; DOPAMINE RECEPTOR AFFECTING AGENT; N1 (2 METHOXYPHENYL)PIPERAZINE; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ANIMAL CELL; ARTICLE; BINDING AFFINITY; DRUG CONFORMATION; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; DRUG TARGETING; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MENTAL DISEASE; MODEL; NEUROLOGIC DISEASE; NONHUMAN; PHARMACOPHORE;

ANIMALS; CELL LINE; CINNAMATES; CRICETINAE; DOPAMINE AGONISTS; HUMANS; LIGANDS; MITOGENS; MODELS, MOLECULAR; PIPERAZINES; RADIOLIGAND ASSAY; RECEPTORS, DOPAMINE D2; RECEPTORS, DOPAMINE D3; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; THYMIDINE;

EID: 0041919650     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030836n     Document Type: Article

References (62)

1. Jackson, D. M.; Westlind-Danielson, A. Dopamine Receptors: Molecular Biology, Biochemistry and Behavioural Aspects. Pharmacol. Ther. 1994, 64, 291-370.
2. Missale, C.; Nash, S. R.; Robinson, S. W.; Jaber, M.; Caron, M. G. Dopamine Receptors: From Structure to Function. Physiol. Rev. 1998, 78, 189-225.
3. Strange, P. G. Antipsychotic Drugs: Importance of Dopamine Receptors for Mechanisms of Therapeutic Actions and Side Effects. Pharmacol. Rev. 2001, 53, 119-133.
4. 3) as a Target for Neuroleptics. Nature 1990, 347, 146-151.
5. 3 Dopamine Receptor: Neurology and Potential Clinical Relevance. Pharmacol. Rev. 1997, 49, 231-252.
6. Luedtke, R. R.; Mach, R. H. Progress in Developing D3 Dopamine Receptor Ligands as Potential Therapeutic Agents for Neurological and Neuropsychiatric Disorders. Curr. Pharm. Des. 2003, 9, 643-671.
7. 3 Receptor in Schizophrenia and in Antipsychotic Drug Actions. Brain Res. Brain Res. Rev. 2000, 31, 277-287.
8. Pinter, M. M.; Rutgers, A. W.; Hebenstreit, E. An Open-Label, Multicentre Clinical Trial to Determine the Levodopa Dose-Sparing Capacity of Pramipexole in Patients with Idiopathic Parkinson's Disease. J. Neural. Transm. 2000, 107, 1307-1323.
9. Möller, J. C.; Oertel, W. H. Pramipexole in the Treatment of Advanced Parkinson's Disease. Eur. J. Neurol. 2000, 7 Suppl 1, 21-25.
10. 3 Receptor Function. Nat. Med. 2003, 9, 762-767.
11. Sokoloff, P.; Bézard, E.; Ferry, S.; Stark, H.; Groß, C. DOPAMINE 2002 Meeting, Portland, OR, July 10-14, 2002; Abstract book, S10.4.
12. 3 Receptor Agents as Potential New Medications for Drug Addiction. Eur. Psychiatry 2000, 15, 140-146.
13. Everitt, B. J.; Robbins, T. W. Second-order Schedules of Drug Reinforcement in Rats and Monkeys: Measurement of Reinforcing Efficacy and Drug-seeking Behaviour. Psychopharmacology (Berlin) 2000, 153, 17-30.
14. 3 Receptor Ligands with Antagonist Properties. ChemBioChem 2002, 3, 946-961.
15. 3 Receptor Antagonists. Bioorg. Med. Chem. Lett. 1998, 8, 2715-2718.
16. 3 Receptor Antagonists and Partial Agonists. J. Med. Chem. 2002, 45, 4594-4597.
17. 3 Receptor. Bioorg. Med. Chem. Lett. 1995, 5, 219-222.
18. 3 Receptor Agonist. Nature 1999, 400, 371-375.
19. 3 Dopamine Receptor Ligands. Bioorg. Med. Chem. Lett. 1997, 7, 2403-2408.
20. 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.
21. Cha, M. Y.; Choi, B. C.; Kang, K. H.; Pae, A. N.; Choi, K. I.; Cho, Y. S.; Koh, H. Y.; Lee, H. Y.; Jung, D.; Kong, J. Y. Design and Synthesis of a Piperazinylalkylisoxazole Library for Subtype Selective Dopamine Receptor Ligands. Bioorg. Med. Chem. Lett. 2002, 12, 1327-1330.
22. 3 Ligands: II. 2-[4-[3-(4-Aryl-1-piperazinyl)propoxy]phenyl]benzimidazole Partial Agonists. Bioorg. Med. Chem. Lett. 1995, 5, 2547-2550.
23. 3 Receptor Ligands. Pharmazie 2001, 56, 287-289.
24. 3 Receptor Ligands. J. Med. Chem. 2002, 45, 5727-5735.
25. Preti, A. BP-897 Bioprojet. Curr. Opin. Invest. Drugs 2000, 1, 110-115.
26. Spielberger, G. In Houben-Weyl, 11/1 ed.; Büchel, K. H., Falbe, J., Hagemann, H., Hanack, M., Klamann, D., Kreher, R., Kropf, H., Reglitz, M., Schaumann, E., Eds.; Thieme: Stuttgart, 1957; pp 24-108.
27. 1A Agonist 8-Hydroxy-2-(di-n-propylamino)tetralin (8-OH-DPAT). Eur. J. Pharmacol. 1988, 154, 339-341.
28. Lavrinovics, E.; Grinsteins, V. Preparation of Phthalimidoalkyl Piperazines. Patent SU 193524 March 13, 1967.
29. Wu, Y.-H.; Smith, K. R.; Rayburn, J. W.; Kissel, J. W. Psycho-sedative Agents. N-(4-Phenyl-1-piperazinylalkyl)-Substituted Cyclic Imides. J. Med. Chem. 1969, 12, 876-881.
30. Gribble, G. W.; Lord, P. D.; Skotnicki, J.; Dietz, S. E.; Eaton, J. T.; Johnson, J. L. Reactions of Sodium Borohydride in Acidic Media. I. Reduction of Indoles and Alkylation of Aromatic Amines with Carboxylic Acids. J. Am. Chem. Soc. 1974, 96, 7812-7814.
31. Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures. J. Org. Chem. 1996, 61, 3849-3862.
32. Ramanjulu, J. M.; Joullie, M. M. N-Alkylation of Amino Acid Esters Using Sodium Triacetoxyborohydride. Synth. Commun. 1996, 26, 1379-1384.
33. 1-Adrenoreceptor Antagonists. Eur. Pat. Appl. EP 1996, 711, 757; Chem. Abstr. 1996, 125, 86679n.
34. Depreux, P.; Aichaoui, H.; Lesieur, I. Synthesis of Indanyl Analogs of 3-[3-(4-Arylpiperazin-1-yl)propyl]-2-oxo-2,3-dihydro-[1,3]benzoxazoles. Heterocycles 1993, 36, 1051-1058.
35. Saji, I.; Muto, M.; Tanno, N.; Yoshigi, M. Preparation of [[[(Carboximidomethyl)cycloalkyl]methyl]azinyl]arenes as Antipsychotics. Eur. Pat. Appl. 1992, 464, 846; Chem. Abstr. 1992, 116, 151794b.
36. Yevich, J. P.; New, J. S.; Smith, D. W.; Lobeck, W. G.; Catt, J. D.; Minelli, J. L.; Eison, M. S.; Taylor, D. P.; Riblet, L. A.; Temple, D. L. Jr. Synthesis and Biological Evaluation of 1-(1,2-Benzisothiazol-3-yl)- and (1,2-Benzisoxazol-3-yl)piperazine Derivatives as Potential Antipsychotic Agents. J. Med. Chem. 1986, 29, 359-369.
37. Azizian, H.; Eaborn, C.; Pidcock, A. Synthesis of Organotrialkylstannanes. The Reaction between Organic Halides and Hexaalkyldistannanes in the Presence of Palladium Complexes. J. Organomet. Chem. 1981, 215, 49-58.
38. 3-Receptor. J. Labelled. Compd. Radiopharm. 1997, 39, 601-606.
39. SYBYL, version 6.5; Tripos Associates, Inc.: St. Louis, MO, 2001.
40. Gasteiger, J.; Marsili, M. Iterative Partial Equalization of Orbital Electronegativity - A Rapid Access to Atomic Charges. Tetrahedron 1980, 36, 3219-3288.
41. Lemmen, C.; Lengauer, T.; Klebe, G. FLEXS: A Method for Fast Flexible Ligand Superposition. J. Med. Chem. 1998, 41, 4502-4520.
42. 4 Receptors. Bioorg. Med. Chem. Lett. 1999, 9, 1285-1290.
43. 3 Receptor. Bioorg. Med. Chem. Lett. 1998, 8, 2859-2864.
44. Cambridge Structural Database, Cambridge Crystallographic Data Center, Cambridge, U.K.
45. GRID, version 16; Molecular Discovery Ltd.: Oxford, 2000.
46. Palczewski, K.; Kumasaka, T.; Hori, T.; Behnke, C. A.; Motoshima, H.; Fox, B. A.; Le Trong, I.; Teller, D. C.; Okada, T.; Stenkamp, R. E.; Yamamoto, M.; Miyano, M. Crystal Structure of Rhodopsin: A G Protein-Coupled Receptor. Science 2000, 289, 739-745.
47. Ballesteros, J. A.; Shi, L.; Javitch, J. A. Structural Mimicry in G Protein-Coupled Receptors: Implications of the High-Resolution Structure of Rhodopsin for Structure - Function Analysis of Rhodopsin-Like Receptors. Mol. Pharmacol. 2001, 60, 1-19.
48. Insight II/Discover, Version 2000; Accelrys Inc.: San Diego, 2000.
49. Rarey, M.; Kramer, B.; Lengauer, T. Time-Efficient Docking of Flexible Ligands into Active Sites of Proteins. Proc. Int. Conf Intell. Syst. Mol. Biol. 1995, 3, 300-308.
50. 2 Receptor. Eur. J. Pharmacol. [Mol. Pharmacol. Sec.] 1992, 225, 331-337.
51. 3H]hydroxy-NN-di-n-propyl-2-aminotetralin. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 8155-8159.
52. 50) of an Enzymatic Reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
53. Wright, J.; Downing, D.; Heffner, T.; Pugsley, T.; MacKenzie, R.; Wise, L. Discovery of Selective Dopamine D3 Ligands: I. Dimeric 2-[4-[3-Aminopropoxy)phenyl]benzimidazole Antagonists. Bioorg. Med. Chem. Lett. 1995, 5, 2541-2546.
54. 1A Serotonin Antagonist 1-(2-Methoxyphenyl)-4-[4-(2-phthalimido)butyl]-piperazine with Reduced α1-Adrenergic Affinity. J. Med. Chem. 1991, 34, 2633-2638.
55. 3 Receptor Subtype. J. Med. Chem. 2001, 44, 3175-3186.
56. 3 Receptor. Bioorg. Med. Chem. Lett. 1999, 9, 179-184.
57. Gowing, L. R.; Henry-Edwards, S. M.; Irvine, R. J.; Ali, R. L. The Health Effects of Ecstasy: A Literature Review. Drug Alcohol Rev. 2002, 21, 53-63.
58. 1A Affinity/Selectivity. J. Med. Chem. 1999, 42, 36-49.
59. Wicke, K.; Garcia-Ladona, J. The dopamine D3 receptor partial agonist, BP 897, is an antagonist at human dopamine D3 receptors and at rat somatodendritic dopamine D3 receptors. Eur. J. Pharmacol. 2001, 424, 85-90.
60. 3 receptor antagonism inhibits cocaine-seeking and cocaine-enhanced brain reward in rats. J. Neurosci. 2002, 22, 9595-9603.
61. 3 Receptor in a Transfected NG 108-15 Neuroblastoma-Glioma Hybrid Cell Line. Eur. J. Pharmacol. 1994, 268, 129-139.
62. 3 Receptor Antagonist, Activates Locomotion in Rodents. J. Pharmacol. Exp. Ther. 1995, 275, 1239-1246.