Design, synthesis, and structure-affinity relationships of regioisomeric N-benzyl alkyl ether piperazine derivatives as σ-1 receptor ligands

Journal of Medicinal Chemistry

Volumn 53, Issue 16, 2010, Pages 6228-6239

  Moussa, Iman A ^a   Banister, Samuel D ^a   Beinat, Corinne ^a   Giboureau, Nicolas ^b   Reynolds, Aaron J ^a   Kassiou, Michael ^a,b  

^a UNIVERSITY OF SYDNEY   (Australia)

^b UNIVERSITY OF SYDNEY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON 11; N (BENZOFURAN 2 YLMETHYL) N' (2' PROPOXYBENZYL)PIPERAZINE; N (BENZOFURAN 2 YLMETHYL) N' (3' ETHOXYBENZYL)PIPERAZINE; N (BENZOFURAN 2 YLMETHYL) N' (3' PROPOXYBENZYL)PIPERAZINE; N (BENZOFURAN 2 YLMETHYL) N' (4' ETHOXYBENZYL)PIPERAZINE; N (BENZOFURAN 2 YLMETHYL) N' (4' PROPOXYBENZYL)PIPERAZINE; N (BENZOFURAN 2 YLMETHYL) N' [2' (3'' FLUOROPROPOXY)BENZYL)PIPERAZINE; N (BENZOFURAN 2 YLMETHYL) N' [3' (2''FLUOROETHOXY)BENZYL]PIPERAZINE; N (BENZOFURAN 2 YLMETHYL) N' [3' (3'' FLUOROPROPOXY)BENZYL)-PIPERAZINE; N (BENZOFURAN 2 YLMETHYL) N' [4' (2'' FLUOROETHOXY)BENZYL]PIPERAZINE; N (BENZOFURAN 2 YLMETHYL) N' [4' (3'' FLUOROPROPOXY)BENZYL]PIPERAZINE; N (BENZOFURAN 2 YLMETHYL)N' (4' METHOXYBENZYL)PIPERAZINE; N [(BENZOFURAN 2 YL)METHYL) N' [2' (2'' FLUOROETHOXY)BENZYL]PIPERAZINE; N [(BENZOFURAN 2 YL)METHYL] N' (2' ETHOXYBENZYL)PIPERAZINE; N [(BENZOFURAN 2 YL)METHYL] N' (2' METHOXYBENZYL)PIPERAZINE; N [(BENZOFURAN 2 YL)METHYL] N' (3' METHOXYBENZYL)PIPERAZINE; N(BENZOFURAN 2 YLMETHYL)N' [4' (2'' FLUOROETHOXY)BENZYL]PIPERAZINE; PIPERAZINE DERIVATIVE; SIGMA RECEPTOR LIGAND; TRACER; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BABOON; BRAIN LEVEL; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; DRUG UPTAKE; IN VITRO STUDY; IN VIVO STUDY; MALE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; STRUCTURE ACTIVITY RELATION;

ANIMALS; BENZOFURANS; BINDING, COMPETITIVE; BRAIN; CARBON RADIOISOTOPES; ETHERS; LIGANDS; PAPIO; PC12 CELLS; PIPERAZINES; POSITRON-EMISSION TOMOGRAPHY; RADIOLIGAND ASSAY; RADIOPHARMACEUTICALS; RATS; RECEPTORS, SIGMA; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TISSUE DISTRIBUTION;

EID: 77955869129     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100639f     Document Type: Article

References (85)

1. Martin, W. R.; Eades, C. G.; Thompson, J. A.; Huppler, R. E.; Gilbert, P. E. The effects of morphine- and nalorphine-like drugs in the nondependent and morphine-dependent chronic spinal dog J. Pharmacol. Exp. Ther. 1976, 197, 517-532
2. Quirion, R.; Chicheportiche, R.; Contreras, P. C.; Johnson, K. M.; Lodge, D.; Tam, S. W.; Woods, J. H.; Zukin, S. R. Classification and nomenclature of phencyclidine and sigma receptor sites Trends Neurosci. (Pers. Ed.) 1987, 10, 444-446
3. Quirion, R.; Bowen, W. D.; Itzhak, Y.; Junien, J. L.; Musacchio, J. M.; Rothman, R. B.; Su, T. P.; Tam, S. W.; Taylor, D. P. A proposal for the classification of sigma binding sites Trends Pharmacol. Sci. 1992, 13, 85-86
4. Hanner, M.; Moebius, F. F.; Flandorfer, A.; Knaus, H. G.; Striessnig, J.; Kempner, E.; Glossmann, H. Purification, molecular cloning, and expression of the mammalian sigma1-binding site Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8072-8077
5. Kekuda, R.; Prasad, P. D.; Fei, Y. J.; Leibach, F. H.; Ganapathy, V. Cloning and functional expression of the human type 1 sigma receptor (hSigmaR1) Biochem. Biophys. Res. Commun. 1996, 229, 553-558
6. Colabufo, N. A.; Berardi, F.; Abate, C.; Contino, M.; Niso, M.; Perrone, R. Is the sigma2 receptor a histone binding protein? J. Med. Chem. 2006, 49, 4153-4158
7. 2 Receptor Ligand PB28 with the Human Nucleosome: Computational and Experimental Probes of Interaction with the H2A/H2B Dimer ChemMedChem 2010, 5, 268-273
8. Su, T. P.; London, E. D.; Jaffe, J. H. Steroid binding at sigma receptors suggests a link between endocrine, nervous, and immune systems Science 1988, 240, 219-221
9. Monnet, F. P.; Maurice, T. The sigma1 protein as a target for the non-genomic effects of neuro(active)steroids: molecular, physiological, and behavioral aspects J. Pharmacol. Sci. 2006, 100, 93-118
10. Fontanilla, D.; Johannessen, M.; Hajipour, A. R.; Cozzi, N. V.; Jackson, M. B.; Ruoho, A. E. The Hallucinogen N,N-Dimethyltryptamine (DMT) Is an Endogenous Sigma-1 Receptor Regulator Science 2009, 323, 934-937
11. Su, T.-P.; Hayashi, T.; Vaupel, D. B. When the endogenous hallucinogenic trace amine N,N-dimethyltryptamine meets the sigma-1 receptor Sci. Signal. 2009, 2, pe12
12. Hayashi, T.; Rizzuto, R.; Hajnoczky, G.; Su, T.-P. MAM: More than just a housekeeper Trends Cell Biol. 2009, 19, 81-88
13. 2+ signaling and cell survival Cell 2007, 131, 596-610
14. Tsai, S.-Y.; Hayashi, T.; Mori, T.; Su, T.-P. Sigma-1 receptor chaperones and diseases Cent. Nerv. Syst. Agents Med. Chem. 2009, 9, 184-189
15. 2+ concentration J. Pharmacol. Exp. Ther. 2000, 293, 788-798
16. + channels in rat neurohypophysial terminals requires neither G-protein nor ATP J. Physiol. 2000, 526, 527-539
17. Zhang, H.; Cuevas, J. Sigma receptors inhibit high-voltage-activated calcium channels in rat sympathetic and parasympathetic neurons J. Neurophysiol. 2002, 87, 2867-2879
18. Aydar, E.; Palmer, C. P.; Klyachko, V. A.; Jackson, M. B. The sigma receptor as a ligand-regulated auxiliary potassium channel subunit Neuron 2002, 34, 399-410
19. 2+: clinical and therapeutic relevance Biol. Cell 2005, 97, 873-883
20. Vilner, B. J.; Bowen, W. D. Modulation of cellular calcium by sigma-2 receptors: release from intracellular stores in human SK-N-SH neuroblastoma cells J. Pharmacol. Exp. Ther. 2000, 292, 900-911
21. Matsuno, K.; Matsunaga, K.; Senda, T.; Mita, S. Increase in extracellular acetylcholine level by sigma ligands in rat frontal cortex J. Pharmacol. Exp. Ther. 1993, 265, 851-859
22. Kobayashi, T.; Matsuno, K.; Nakata, K.; Mita, S. Enhancement of acetylcholine release by SA4503, a novel sigma 1 receptor agonist, in the rat brain J. Pharmacol. Exp. Ther. 1996, 279, 106-113
23. 3H- acetylcholine from striatal and hippocampal rat brain slices Synapse 2002, 46, 1-3
24. 3H]dopamine release from rat striatal slices by sigma receptor ligands J. Pharmacol. Exp. Ther. 1994, 271, 212-219
25. 3H]dopamine release via a presynaptic mechanism Eur. J. Pharmacol. 1995, 294, 713-719
26. 3H] dopamine release from mesolimbic and mesocortical areas of guinea pig brain by sigma receptors Schizophr. Res. 1996, 21, 51-62
27. 3H]dopamine from guinea pig striatal slices is modulated by sigma1 receptor agonists Naunyn-Schmiedeberg's Arch. Pharmacol. 1997, 356, 455-461
28. Hayashi, T.; Kagaya, A.; Takebayashi, M.; Shimizu, M.; Uchitomi, Y.; Motohashi, N.; Yamawaki, S. Modulation by sigma ligands of intracellular free Ca++ mobilization by N-methyl-D-aspartate in primary culture of rat frontal cortical neurons J. Pharmacol. Exp. Ther. 1995, 275, 207-214
29. Debonnel, G.; de Montigny, C. Modulation of NMDA and dopaminergic neurotransmissions by sigma ligands: possible implications for the treatment of psychiatric disorders Life Sci. 1996, 58, 721-734
30. Bermack, J. E.; Debonnel, G. Modulation of serotonergic neurotransmission by short- and long-term treatments with sigma ligands Br. J. Pharmacol. 2001, 134, 691-699
31. Lucas, G.; Rymar, V. V.; Sadikot, A. F.; Debonnel, G. Further evidence for an antidepressant potential of the selective sigma1 agonist SA 4503: electrophysiological, morphological and behavioural studies Int. J. Neuropsychopharmacol. 2008, 11, 485-495
32. Monnet, F. P.; Debonnel, G.; de Montigny, C. In vivo electrophysiological evidence for a selective modulation of N-methyl-D-aspartate-induced neuronal activation in rat CA3 dorsal hippocampus by sigma ligands J. Pharmacol. Exp. Ther. 1992, 261, 123-130
33. 3H]norepinephrine release evoked by N-methyl-D-aspartate in the rat hippocampus Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 3774-3778
34. 3H]-noradrenaline release in rat hippocampal slices Br. J. Pharmacol. 1996, 119, 65-72
35. Hashimoto, K.; Ishiwata, K. Sigma receptor ligands: Possible application as therapeutic drugs and as radiopharmaceuticals Curr. Pharm. Des. 2006, 12, 3857-3876
36. Cobos, E. J.; Entrena, J. M.; Nieto, F. R.; Cendán, C. M.; Del Pozo, E. Pharmacology and Therapeutic Potential of Sigma1 Receptor Ligands Curr. Neuropharmacol. 2008, 6, 344-366
37. Maurice, T.; Su, T.-P. The pharmacology of sigma-1 receptors Pharmacol. Ther. 2009, 124, 195-206
38. 3H]haloperidol binding in guinea pig brain membranes Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 5618-5621
39. Frieboes, R.-M.; Steiger, A. The antipsychotic effects of sigma drugs. In Neurotransmitter Receptors in Actions of Antipsychotic Medications; Lidow, M. S., Ed.; CRC Press: Boca Raton, 2000; pp 137 - 152.
40. Itzhak, Y.; Kassim, C. O. Clorgyline displays high affinity for sigma binding sites in C57BL/6 mouse brain Eur. J. Pharmacol. 1990, 176, 107-108
41. Narita, N.; Hashimoto, K.; Tomitaka, S.; Minabe, Y. Interactions of selective serotonin reuptake inhibitors with subtypes of sigma receptors in rat brain Eur. J. Pharmacol. 1996, 307, 117-119
42. Bermack, J. E.; Debonnel, G. The role of sigma receptors in depression J. Pharmacol. Sci. 2005, 97, 317-336
43. 1) receptor and its role in the treatment of mood disorders Drugs Future 2009, 34, 137-146
44. Kulkarni, S. K.; Dhir, A. σ-1 receptors in major depression and anxiety Expert Rev. Neurother. 2009, 9, 1021-1034
45. Matsumoto, R. R.; McCracken, K. A.; Pouw, B.; Zhang, Y.; Bowen, W. D. Involvement of sigma receptors in the behavioral effects of cocaine: evidence from novel ligands and antisense oligodeoxynucleotides Neuropharmacology 2002, 42, 1043-1055
46. 1) receptor antagonists represent a new strategy against cocaine addiction and toxicity Neurosci. Biobehav. Rev. 2002, 26, 499-527
47. Matsumoto, R. R.; Liu, Y.; Lerner, M.; Howard, E. W.; Brackett, D. J. Sigma receptors: Potential medications development target for anti-cocaine agents Eur. J. Pharmacol. 2003, 469, 1-12
48. Nguyen, E. C.; McCracken, K. A.; Liu, Y.; Pouw, B.; Matsumoto, R. R. Involvement of sigma (σ) receptors in the acute actions of methamphetamine: Receptor binding and behavioral studies Neuropharmacology 2005, 49, 638-645
49. Romieu, P.; Maurice, T. The sigma1 (s1) protein as a new target for anti-cocaine therapy. In Cocaine and Heroin Abuse Research; Pizzoli, L. A., Ed.; Nova Science Publishers: Hauppauge, NY, 2006; pp 37 - 60.
50. John, C. S.; Bowen, W. D.; Varma, V. M.; McAfee, J. G.; Moody, T. W. Sigma receptors are expressed in human non-small cell lung carcinoma Life Sci. 1995, 56, 2385-2392
51. Vilner, B. J.; John, C. S.; Bowen, W. D. Sigma-1 and sigma-2 receptors are expressed in a wide variety of human and rodent tumor cell lines Cancer Res. 1995, 55, 408-413
52. Wang, B.; Rouzier, R.; Albarracin, C. T.; Sahin, A.; Wagner, P.; Yang, Y.; Smith, T. L.; Bernstam, F. M.; Marcelo, A. C.; Hortobagyi, G. N.; Pusztai, L. Expression of sigma 1 receptor in human breast cancer Breast Cancer Res. Treat. 2004, 87, 205-214
53. Vilner, B. J.; de Costa, B. R.; Bowen, W. D. Cytotoxic effects of sigma ligands: sigma receptor-mediated alterations in cellular morphology and viability J. Neurosci. 1995, 15, 117-134
54. Moody, T. W.; Leyton, J.; John, C. Sigma ligands inhibit the growth of small cell lung cancer cells Life Sci. 2000, 66, 1979-1986
55. Berthois, Y.; Bourrie, B.; Galiegue, S.; Vidal, H.; Carayon, P.; Martin, P. M.; Casellas, P. SR31747A is a sigma receptor ligand exhibiting antitumoural activity both in vitro and in vivo Br. J. Cancer 2003, 88, 438-446
56. Crawford, K. W.; Bowen, W. D. Sigma-2 receptor agonists activate a novel apoptotic pathway and potentiate antineoplastic drugs in breast tumor cell lines Cancer Res. 2002, 62, 313-322
57. Aydar, E.; Palmer, C. P.; Djamgoz, M. B. Sigma receptors and cancer: Possible involvement of ion channels Cancer Res. 2004, 64, 5029-5035
58. Wheeler, K. T.; Wang, L. M.; Wallen, C. A.; Childers, S. R.; Cline, J. M.; Keng, P. C.; Mach, R. H. Sigma-2 receptors as a biomarker of proliferation in solid tumours Br. J. Cancer 2000, 82, 1223-1232
59. Collier, T. L.; Waterhouse, R. N.; Kassiou, M. Imaging sigma receptors: Applications in drug development Curr. Pharm. Des. 2007, 13, 51-72
60. Glennon, R. A.; Ablordeppey, S. Y.; Ismaiel, A. M.; el-Ashmawy, M. B.; Fischer, J. B.; Howie, K. B. Structural features important for sigma 1 receptor binding J. Med. Chem. 1994, 37, 1214-1219
61. Ablordeppey, S. Y.; Fischer, J. B.; Glennon, R. A. Is a nitrogen atom an important pharmacophoric element in sigma ligand binding? Bioorg. Med. Chem. 2000, 8, 2105-2111
62. Ablordeppey, S. Y.; Fischer, J. B.; Law, H.; Glennon, R. A. Probing the proposed phenyl-A region of the sigma-1 receptor Bioorg. Med. Chem. 2002, 10, 2759-2765
63. 1) receptor binding: application of the "deconstruction- reconstruction-elaboration" approach Mini Rev. Med. Chem. 2005, 5, 927-940
64. Cratteri, P.; Romanelli, M. N.; Cruciani, G.; Bonaccini, C.; Melani, F. GRIND-derived pharmacophore model for a series of alpha-tropanyl derivative ligands of the sigma-2 receptor J. Comput.-Aided Mol. Des. 2004, 18, 361-374
65. 2) Receptor Ligands Cent. Nerv. Syst. Agents Med. Chem. 2009, 9, 246-257
66. 2 receptors based on a series of substituted benzo[d]oxazol-2(3H)-one derivatives Bioorg. Med. Chem. Lett. 2010, 20, 2954-2957
67. Banister, S. D.; Moussa, I. A.; Jordan, M. J. T.; Coster, M. J.; Kassiou, M. Oxo-bridged isomers of aza-trishomocubane sigma (σ) receptor ligands: Synthesis, in vitro binding, and molecular modeling Bioorg. Med. Chem. Lett. 2010, 20, 145-148
68. Liu, X.; Banister, S. D.; Christie, M. J.; Banati, R.; Meikle, S.; Coster, M. J.; Kassiou, M. Trishomocubanes: Novel sigma ligands modulate cocaine-induced behavioural effects Eur. J. Pharmacol. 2007, 555, 37-42
69. Baziard-Mouysset, G.; Younes, S.; Labssita, Y.; Payard, M.; Caignard, D.-H.; Rettori, M.-C.; Renard, P.; Pfeiffer, B.; Guardiola-Lemaitre, B. Synthesis and structure-activity relationships of novel 2-amino alkyl chromones and related derivatives as s site-selective ligands Eur. J. Med. Chem. 1998, 33, 339-347
70. Younes, S.; Labssita, Y.; Baziard-Mouysset, G.; Payard, M.; Rettori, M.; Renard, P.; Pfeiffer, B.; Caignard, D. Synthesis and structure-activity relationships of novel arylalkyl 4-benzyl piperazine derivatives as sigma site selective ligands Eur. J. Med. Chem. 2000, 35, 107-121
71. Löwik, D. W. P. M.; Lowe, C. R. Synthesis of Macrocyclic, Triazine-Based Receptor Molecules Eur. J. Org. Chem. 2001, 2001, 2825-2839
72. Carpino, L. A.; Mansour, E. M. E.; Cheng, C. H.; Williams, J. R.; MacDonald, R.; Knapczyk, J.; Carman, M.; Lopusinski, A. Polystyrene-based deblocking-scavenging agents for the 9-fluorenylmethyloxycarbonyl amino-protecting group J. Org. Chem. 1983, 48, 661-665
73. Tahtaoui, C.; Parrot, I.; Klotz, P.; Guillier, F.; Galzi, J.-L.; Hibert, M.; Ilien, B. Fluorescent Pirenzepine Derivatives as Potential Bitopic Ligands of the Human M1Muscarinic Receptor J. Med. Chem. 2004, 47, 4300-4315
74. 3H](+)-pentazocine labeled sigma sites in mouse spinal cord by chronic morphine treatment Eur. J. Pharmacol. 1998, 350, 47-52
75. Eckleman, W. C. The Design of Site-Directed Radiopharmaceuticals for Use in Drug Discovery. In Nuclear Imaging in Drug Discovery, Development and Approval; Burns, D. H.; Gibson, R. E.; Dannals, R. F.; Siegl, P. K., Eds.; Birkhäuser: Boston, 1993; pp 113 - 134.
76. Quinlivan, M.; Mattner, F.; Papazian, V.; Zhou, J.; Katsifis, A.; Emond, P.; Chalon, S.; Kozikowski, A.; Guilloteau, D.; Kassiou, M. Synthesis and evaluation of iodine-123 labelled tricyclic tropanes as radioligands for the serotonin transporter Nucl. Med. Biol. 2003, 30, 741-746
77. 123I]-1-(iodopropen-2-yl)- 4-[(4-cyanophenoxy)methyl]piperidine J. Med. Chem. 1997, 40, 1657-1667
78. 3H]1,3-di-o-tolylguanidine (DTG) binding sites in guinea pig brain: a comparative study Brain Res. 1992, 581, 33-38
79. 3H](+)pentazocine binding sites in the rat brain: autoradiographic visualization of the putative sigma1 and sigma2 receptor subtypes Neuroscience 1997, 76, 467-477
80. Honer, M.; Bruhlmeier, M.; Missimer, J.; Schubiger, A. P.; Ametamey, S. M. Dynamic Imaging of Striatal D2 Receptors in Mice Using Quad-HIDAC PET J. Nucl. Med. 2004, 45, 464-470
81. 11C]SA4503: Radiation dosimetry,in vivo selectivity and PET imaging of sigma1 receptors in the cat brain Ann. Nucl. Med. 2000, 14, 285-292
82. 18F] haloperidol binding in baboon brain in vivo Nucl. Med. Biol. 1996, 23, 47-52
83. 18F]N-methylspiroperidol by extrastriatal dopamine receptors in schizophrenic patients Synapse 1995, 19, 14-17
84. Kabalka, G. W.; Varma, M.; Varma, R. S.; Srivastava, P. C.; Knapp, F. F. The tosylation of alcohols J. Org. Chem. 1986, 51, 2386-2388
85. Parenty, A. D. C.; Smith, L. V.; Cronin, L. An unusual substitution reaction directed by an intramolecular re-arrangement Tetrahedron 2005, 61, 8410-8418