Development of (S)-N6-(2-(4-(isoquinolin-1-yl)piperazin-1-yl) ethyl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]-thiazole-2,6-diamine and its analogue as a D3 receptor preferring agonist: Potent in vivo activity in Parkinson's disease animal models

Journal of Medicinal Chemistry

Volumn 53, Issue 3, 2010, Pages 1023-1037

  Ghosh, Balaram ^a   Antonio, Tamara ^b   Zhen, Juan ^b   Kharkar, Prashant ^a   Reith, Maarten E A ^b   Dutta, Aloke K ^a  

^a WAYNE STATE UNIVERSITY   (United States)

^b NEW YORK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 DIPROPYLAMINO 7 HYDROXYTETRALIN; 5 HYDROXY 2 (DIPROPYLAMINO)TETRALIN; DOPAMINE 2 RECEPTOR; DOPAMINE 3 RECEPTOR; DOPAMINE 3 RECEPTOR STIMULATING AGENT; GUANOSINE 5' O (3 THIOTRIPHOSPHATE); N6 (2 (4 (ISOQUINOLIN 1 YL)PIPERAZIN 1 YL)ETHYL) N6 PROPYL 4,5,6,7 TETRAHYDROBENZO[D] THIAZOLE 2,6 DIAMINE; N6 PROPYL N6 (2 (4 (4 (PYRIDIN 4 YL)PHENYL)PIPERAZIN 1 YL) ETHYL) 4,5,6,7 TETRAHYDROBENZO[D] THIAZOLE 2,6 DIAMINE; N6 PROPYL N6 (2 (4 (QUINOLIN 4 YL)PIPERAZIN 1 YL)ETHYL) 4,5,6,7 TETRAHYDROBENZO[D]THIAZOLE 2,6 DIAMINE; N6 PROPYL N6 (2 (4 (QUINOLIN 5 YL)PIPERAZIN 1 YL)ETHYL) 4,5,6,7 TETRAHYDROBENZO[D]THIAZOLE 2,6 DIAMINE; OXIDOPAMINE; SCAVENGER; UNCLASSIFIED DRUG; ANTIPARKINSON AGENT; BENZOTHIAZOLE DERIVATIVE; ISOQUINOLINE DERIVATIVE; N6 (2 (4 (ISOQUINOLIN 1 YL)PIPERAZIN 1 YL)ETHYL) N6 PROPYL 4,5,6,7 TETRAHYDROBENZO(D)THIAZOLE 2,6 NRW; N6-(2-(4-(ISOQUINOLIN-1-YL)PIPERAZIN-1-YL)ETHYL)-N6-PROPYL-4,5,6,7-TETRAHYDROBENZO(D)THIAZOLE-2,6-NRW; RESERPINE; THIAZOLE DERIVATIVE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BINDING ASSAY; CELL STIMULATION; CELL STRAIN HEK293; CHO CELL; CONTROLLED STUDY; DRUG POTENCY; ENZYME ACTIVITY; ENZYME BINDING; ENZYME INHIBITION; EXPERIMENTAL MODEL; HYDROPHOBICITY; IN VIVO STUDY; MALE; NEUROPROTECTION; NONHUMAN; PARKINSON DISEASE; PROTEIN EXPRESSION; RAT; STRUCTURE ACTIVITY RELATION; ANIMAL; CHEMISTRY; CRICETULUS; DISEASE MODEL; DRUG EFFECT; DRUG POTENTIATION; HAMSTER; HUMAN; LOCOMOTION; METABOLISM; MOUSE; RADIOASSAY; SYNTHESIS;

ANIMALS; ANTIPARKINSON AGENTS; BENZOTHIAZOLES; CHO CELLS; CRICETINAE; CRICETULUS; DISEASE MODELS, ANIMAL; FREE RADICAL SCAVENGERS; GUANOSINE 5'-O-(3-THIOTRIPHOSPHATE); HUMANS; ISOQUINOLINES; LOCOMOTION; MICE; PARKINSON DISEASE; RADIOLIGAND ASSAY; RATS; RECEPTORS, DOPAMINE D2; RECEPTORS, DOPAMINE D3; RESERPINE; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 77249109359     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm901184n     Document Type: Article

References (59)

1. Mouradian,M.M. Recent advances in the genetics and pathogenesis of Parkinson disease. Neurology 2002, 58, 179-185.
2. Moore, D. J.; West, A. B.; Dawson, V. L.; Dawson, T. M. Molecular pathophysiology of Parkinson's disease. Annu. Rev. Neurosci. 2005, 28, 57-87.
3. Paulus, W.; Jellinger, K. The neuropathologic basis of different clinical subgroups of Parkinson's disease. J. Neuropathol. Exp. Neurol. 1991, 50, 743-755.
4. Sherer, T. B.; Betarbet, R.; Greenamyre, J. T. Pathogenesis of Parkinson's disease. Curr. Opin. Investig. Drugs 2001, 2, 657-662.
5. Wooten, G. F. Movement Disorders. Neurologic Principles and Practice; McGraw-Hill: New York, NY, 1997; pp 153-160.
6. Forno, L. S. Neuropathology of Parkinson's disease. J. Neuropathol. Exp. Neurol. 1996, 55, 259-272.
7. Spillantini, M. G.; Schmidt, M. L.; Lee, V. M.; Trojanowski, J. Q.; Jakes, R.; Goedert, M. Alpha-synuclein in Lewy bodies. Nature 1997, 388, 839-840.
8. Jenner, P. Oxidative stress in Parkinson's disease. Ann. Neurol. 2003, 53 Suppl 3, S26-S36; discussion S36-S38.
9. Dawson, T. M.; Dawson, V. L. Molecular pathways of neurodegeneration in Parkinson's disease. Science 2003, 302, 819-822.
10. Betarbet, R.; Sherer, T. B.; MacKenzie, G.; Garcia-Osuna, M.; Panov, A. V.; Greenamyre, J. T. Chronic systemic pesticide exposure reproduces features of Parkinson's disease. Nat. Neurosci. 2000, 3, 1301-1306.
11. Olanow, C. W.; Tatton, W. G. Etiology and pathogenesis of Parkinson's disease. Annu. Rev. Neurosci. 1999, 22, 123-144.
12. Polymeropoulos, M. H.; Lavedan, C.; Leroy, E.; Ide, S. E.; Dehejia, A.; Dutra, A.; Pike, B.; Root, H.; Rubenstein, J.; Boyer, R.; Stenroos, E. S.; Chandrasekharappa, S.; Athanassiadou, A.; Papapetropoulos, T.; Johnson, W. G.; Lazzarini, A. M.; Duvoisin, R. C.; Di Iorio, G.; Golbe, L. I.; Nussbaum, R. L. Mutation in the alpha-synuclein gene identified in families with Parkinson's disease. Science 1997, 276, 2045-2047.
13. Kruger, R.; Kuhn, W.; Muller, T.; Woitalla, D.; Graeber, M.; Kosel, S.; Przuntek, H.; Epplen, J. T.; Schols, L.; Riess, O. Ala30Pro mutation in the gene encoding alpha-synuclein in Parkinson's disease. Nat. Genet. 1998, 18, 106-108.
14. Marsden, C. D.; Parkes, J. D. "On-off" effects in patients with Parkinson's disease on chronic levodopa therapy. Lancet 1976, 1, 292-296.
15. Foley, P.; Gerlach, M.; Double, K. L.; Riederer, P. Dopamine receptor agonists in the therapy of Parkinson's disease. J. Neural Transm. 2004, 111, 1375-1446.
16. Schapira, A. H.; Olanow, C. W. Rationale for the use of dopamine agonists as neuroprotective agents in Parkinson's disease. Ann. Neurol. 2003, 53 Suppl 3, S149-S57; discussion S157-S159.
17. Clarke, C. E.; Guttman, M. Dopamine agonist monotherapy in Parkinson's disease. Lancet 2002, 360, 1767-1769.
18. Lledo, A. Dopamine agonists: the treatment for Parkinson's disease in the XXI century? Parkinson Relat. Disord. 2001, 7, 51-58.
19. Dutta, A. K.; L., W. Existing Dopaminergic Therapies for Parkinson's Disease. Expert Opin. Ther. Patents 2006, 16, 1613-1625.
20. Kebabian, J. W.; Calne, D. B. Multiple receptors for dopamine. Nature 1979, 277, 93-96.
21. Giros, B.; Martres, M. P.; Sokoloff, P.; Schwartz, J. C. Gene cloning of human dopaminergic D3 receptor and identification of its chromosome. C. R. Acad. Sci. III 1990, 311, 501-508.
22. Sokoloff, P.; Giros, B.; Martres, M. P.; Bouthenet, M. L.; Schwartz, J. C. Molecular cloning and characterization of a novel dopamine receptor (D3) as a target for neuroleptics. Nature 1990, 347, 146-151.
23. 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.
24. Sunahara, R. K.; Guan, H. C.; O'Dowd,B. F.; Seeman, P.; Laurier, L. G.; Ng, G.; George, S. R.; Torchia, J.; Van Tol, H. H.; Niznik, H. B. Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1. Nature 1991, 350, 614-619.
25. Strange, P. G. New insights into dopamine receptors in the central nervous system. Neurochem. Int. 1993, 22, 223-236.
26. Civelli, O.; Bunzow, J. R.; Grandy, D. K. Molecular diversity of the dopamine receptors. Annu. Rev. Pharmacol. Toxicol. 1993, 33, 281-307.
27. Emilien, G.; Maloteaux, J. M.; Geurts, M.; Hoogenberg, K.; Cragg, S. Dopamine receptors;physiological understanding to therapeutic intervention potential. Pharmacol. Ther. 1999, 84, 133-156.
28. Boeckler, F.; Gmeiner, P. The structural evolution of dopamine D3 receptor ligands: structure-activity relationships and selected neuropharmacological aspects. Pharmacol. Ther. 2006, 112, 281-333.
29. Park, B. H.; Fishburn, C. S.; Carmon, S.; Accili, D.; Fuchs, S. Structural organization of the murine D3 dopamine receptor gene. J. Neurochem. 1995, 64, 482-486.
30. Chen, S.; Zhang, X.; Yang, D.; Du, Y.; Li, L.; Li, X.; Ming, M.; Le, W. D2/D3 receptor agonist ropinirole protects dopaminergic cell line against rotenone-induced apoptosis through inhibition of caspase- and JNK-dependent pathways. FEBS Lett. 2008, 582, 603-610.
31. Bellucci, A.; Collo, G.; Sarnico, I.; Battistin, L.; Missale, C.; Spano, P. Alpha-synuclein aggregation and cell death triggered by energy deprivation and dopamine overload are counteracted by D2/D3 receptor activation. J. Neurochem. 2008, 106, 560-577.
32. Joyce, J. N.; Millan, M. J. Dopamine D3 receptor agonists for protection and repair in Parkinson's disease. Curr. Opin. Pharmacol. 2007, 7, 100-105.
33. Ramirez, A. D.; Wong, S. K.; Menniti, F. S. Pramipexole inhibits MPTP toxicity in mice by dopamine D3 receptor dependent and independent mechanisms. Eur. J. Pharmacol. 2003, 475, 29-35.
34. Gallagher, D. A.; Schrag, A. Impact of newer pharmacological treatments on quality of life in patients with Parkinson's disease. CNS Drugs 2008, 22, 563-586.
35. Yamamoto, M.; Schapira, A. H. Dopamine agonists in Parkinson's disease. Expert. Rev. Neurother. 2008, 8, 671-677.
36. Gu, M.; Iravani, M. M.; Cooper, J. M.; King, D.; Jenner, P.; Schapira, A. H. Pramipexole protects against apoptotic cell death by non-dopaminergic mechanisms. J. Neurochem. 2004, 91, 1075-1081.
37. Joyce, J. N.; Presgraves, S.; Renish, L.; Borwege, S.; Osredkar, T.; Hagner, D.; Replogle, M.; PazSoldan, M.; Millan, M. J. Neuroprotective effects of the novel D3/D2 receptor agonist and antiparkinson agent, S32504, in vitro against 1-methyl-4-phenylpyridinium (MPP+) and in vivo against 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP): a comparison to ropinirole. Exp. Neurol. 2003, 184, 393-407.
38. Willner, P. The mesolimbic dopamine system as a target for rapid antidepressant action. Int. Clin. Psychopharmacol. 1997, 12 (Suppl 3), S7-S14.
39. Corrigan,M.H.;Denahan,A.Q.;Wright,C.E.;Ragual,R. J.;Evans, D. L. Comparison of pramipexole, fluoxetine, and placebo in patients with major depression. Depression Anxiety 2000, 11, 58-65.
40. Newman, A. H.; Grundt, P.; Cyriac, G.; Deschamps, J. R.; Taylor, M.; Kumar, R.; Ho, D.; Luedtke, R. R. N-(4-(4-(2,3-Dichloro- or 2-methoxyphenyl)piperazin-1-yl)butyl)heterobiarylcarboxamides with functionalized linking chains as high affinity and enantioselective D3 receptor antagonists. J. Med. Chem. 2009, 52, 2559-2570.
41. Cavalli, A.; Bolognesi, M. L.; Minarini, A.; Rosini, M.; Tumiatti, V.; Recanatini, M.; Melchiorre, C. Multi-target-directed ligands to combat neurodegenerative diseases. J. Med. Chem. 2008, 51, 347-372.
42. Dutta, A. K.; Fei, X. S.; Reith, M. E. A novel series of hybrid compounds derived by combining 2-aminotetralin and piperazine fragments: binding activity at D2 and D3 receptors. Bioorg. Med. Chem. Lett. 2002, 12, 619-622.
43. Dutta, A. K.; Venkataraman, S. K.; Fei, X. S.; Kolhatkar, R.; Zhang, S.; Reith, M. E. Synthesis and biological characterization of novel hybrid 7-[[2-(4-phenyl-piperazin-1-yl)-ethyl]-propylamino]-5,6,7,8-tetrahydro- naphthalen-2-ol and their heterocyclic bioisosteric analogues for dopamine D2 and D3 receptors. Bioorg. Med. Chem. 2004, 12, 4361-4373.
44. Biswas, S.; Hazeldine, S.; Ghosh, B.; Parrington, I.; Kuzhikandathil, E.; Reith, M. E.; Dutta, A. K. Bioisosteric heterocyclic versions of 7-{[2-(4-phenyl-piperazin-1-yl)ethyl]propylamino}-5,6,7,8-tetrahydronaphth alen-2-ol: identification of highly potent and selective agonists for dopamine D3 receptor with potent in vivo activity. J. Med. Chem. 2008, 51, 3005-3019.
45. Biswas, S.; Zhang, S.; Fernandez, F.; Ghosh, B.; Zhen, J.; Kuzhikandathil, E.; Reith, M. E.; Dutta, A. K. Further structure-activity relationships study of hybrid 7-{[2-(4-phenylpiperazin-1-yl)ethyl]propylamino}- 5,6,7,8-tetrahydronaphtha len-2-ol analogues: identification of a high-affinity D3-preferring agonist with potent in vivo activity with long duration of action. J. Med. Chem. 2008, 51, 101-117.
46. Ling, Z. D.; Robie, H. C.; Tong, C. W.; Carvey, P. M. Both the antioxidant and D3 agonist actions of pramipexole mediate its neuroprotective actions in mesencephalic cultures. J. Pharmacol. Exp. Ther. 1999, 289, 202-210.
47. Zou, L.; Xu, J.; Jankovic, J.; He, Y.; Appel, S. H.; Le, W. Pramipexole inhibits lipid peroxidation and reduces injury in the substantia nigra induced by the dopaminergic neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in C57BL/6 mice. Neurosci. Lett. 2000, 281, 167-170.
48. Wang, T.; Magnin, D. R.; Hamann, L. G. Palladium-catalyzed microwave-assisted amination of 1-bromonaphthalenes and 5- and 8-bromoquinolines. Org. Lett. 2003, 5, 897-900.
49. Madrid, P. B.; Sherrill, J.; Liou, A. P.; Weisman, J. L.; Derisi, J. L.; Guy, R. K. Synthesis of ring-substituted 4-aminoquinolines and evaluation of their antimalarial activities. Bioorg. Med. Chem. Lett. 2005, 15, 10151-10158.
50. Dionne,G.;Humber,L.G.;Asselin,A.;McQuillan, J.;Treasurywala, A. M. Ligand-receptor interactions via hydrogen-bond formation. Synthesis and pharmacological evaluation of pyrrolo and pyrido analogues of the cardiotonic agent 7-hydroxycyclindole. J. Med. Chem. 1986, 29, 1452-1457.
51. Orus, L.; Perez-Silanes, S.; Oficialdegui, A. M.; Martinez-Esparza, J.; Del Castillo, J. C.; Mourelle, M.; Langer, T.; Guccione, S.; Donzella, G.; Krovat, E. M.; Poptodorov, K.; Lasheras, B.; Ballaz, S.; Hervias, I.; Tordera, R.; Del Rio, J.; Monge, A. Synthesis and molecular modeling of new 1-aryl-3-[4-arylpiperazin-1-yl]-1-propane derivatives with high affinity at the serotonin transporter and at 5-HT(1A) receptors. J. Med. Chem. 2002, 45, 4128-4139.
52. Ten Hoeve, W.; Wynberg, H. The design of resolving agents. Chiral cyclic phosphoric acids. J. Org. Chem. 2002, 50, 4508-4514.
53. Brown, D. A.; Mishra, M.; Zhang, S.; Biswas, S.; Parrington, I.; Antonio, T.; Reith, M. E.; Dutta, A. K. Investigation of various Nheterocyclic substituted piperazine versions of 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]- propyl-amino}-5,6,7,8-tetrahydro-na phthalen-2-ol: effect on affinity and selectivity for dopamine D3 receptor. Bioorg. Med. Chem. 2009, 17, 3923-3933.
54. Girennavar, B.; Jayaprakasha, G. K.; Jadegoud, Y.; Nagana Gowda, G. A.; Patil, B. S. Radical scavenging and cytochrome P450 3A4 inhibitory activity of bergaptol and geranylcoumarin from grapefruit. Bioorg. Med. Chem. 2007, 15, 3684-3691.
55. Carlsson, A.; Lindqvist, M.; Magnusson, T. 3,4-Dihydroxyphenylalanine and 5-hydroxytryptophan as reserpine antagonists. Nature 1957, 180, 1200.
56. Ungerstedt, U. 6-Hydroxy-dopamine induced degeneration of central monoamine neurons. Eur. J. Pharmacol. 1968, 5, 107-110.
57. Schonafinger, K. Y.; Christine, M.; Vollman, Anne; Ong, Helen H. Synthesis of 7,8,9,10-tetrahydropyrido[30,40:4,5]pyrrolo[3,2-c] quinolines. J. Heterocycl. Chem. 1988, 25, 535-537.
58. Millan, M. J.; Di Cara, B.; Hill, M.; Jackson, M.; Joyce, J. N.; Brotchie, J.; McGuire, S.; Crossman, A.; Smith, L.; Jenner, P.; Gobert, A.; Peglion, J. L.; Brocco, M. S32504, a novel naphtoxazine agonist at dopamine D3/D2 receptors: II. Actions in rodent, primate, and cellular models of antiparkinsonian activity in comparison to ropinirole. J. Pharmacol. Exp. Ther. 2004, 309, 921-935.
59. McCall, R. B.; Lookingland, K. J.; Bedard, P. J.; Huff, R. M. Sumanirole, a highly dopamine D2-selective receptor agonist: in vitro and in vivo pharmacological characterization and efficacy in animal models of Parkinson's disease. J. Pharmacol. Exp. Ther. 2005, 314, 1248-1256.