Synthesis and biological characterization of 3-substituted 1 H -indoles as ligands of GluN2B-containing N-methyl-d-aspartate receptors. Part 2

Journal of Medicinal Chemistry

Volumn 55, Issue 23, 2012, Pages 10532-10539

  Gitto, Rosaria ^a   De Luca, Laura ^a   Ferro, Stefania ^a   Buemi, Maria R ^a   Russo, Emilio ^b   De Sarro, Giovambattista ^b   Chisari, Mariangela ^c   Ciranna, Lucia ^c   Chimirri, Alba ^a  

^a UNIVERSITY OF MESSINA   (Italy)

^b UNIVERSITY MAGNA GRAECIA OF CATANZARO   (Italy)

^c UNIVERSITY OF CATANIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

(N 1H INDOL 6 METHANESULFONAMIDE 3 YL) 2 (4 BENZYLPIPERIDIN 1 YL)ETHANONE; 4 BENZYL ALPHA (4 HYDROXYPHENYL) BETA METHYL 1 PIPERIDINEPROPANOL; IFENPRODIL; INDOLE DERIVATIVE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; TRAXOPRODIL; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50;

ANIMALS; INDOLES; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MODELS, MOLECULAR; RATS; RATS, WISTAR; RECEPTORS, N-METHYL-D-ASPARTATE; X-RAY DIFFRACTION;

EID: 84871027024     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301508d     Document Type: Article

References (45)

1. Traynelis, S. F.; Wollmuth, L. P.; McBain, C. J.; Menniti, F. S.; Vance, K. M.; Ogden, K. K.; Hansen, K. B.; Yuan, H.; Myers, S. J.; Dingledine, R. Glutamate receptor ion channels: structure, regulation, and function Pharmacol. Rev. 2010, 62, 405-496
2. Mayer, M. L. Emerging models of glutamate receptor ion channel structure and function Structure 2011, 19, 1370-1380
3. Kumar, J.; Schuck, P.; Mayer, M. L. Structure and assembly mechanism for heteromeric kainate receptors Neuron 2011, 71, 319-331
4. Mayer, M. L. Glutamate receptor ion channels: Where do all the calories go? Nat. Struct. Mol. Biol. 2011, 18, 253-254
5. Mayer, M. L. Structure and mechanism of glutamate receptor ion channel assembly, activation and modulation Curr. Opin. Neurobiol. 2011, 21, 283-290
6. Hedegaard, M.; Hansen, K. B.; Andersen, K. T.; Brauner-Osborne, H.; Traynelis, S. F. Molecular pharmacology of human NMDA receptors Neurochem. Int. 2012, 61, 601-609
7. Ogden, K. K.; Traynelis, S. F. New advances in NMDA receptor pharmacology Trends Pharmacol. Sci. 2011, 32, 726-733
8. Niciu, M. J.; Kelmendi, B.; Sanacora, G. Overview of glutamatergic neurotransmission in the nervous system Pharmacol., Biochem. Behav. 2012, 100, 656-664
9. Paoletti, P. Molecular basis of NMDA receptor functional diversity Eur. J. Neurosci. 2011, 33, 1351-1365
10. Mony, L.; Krzaczkowski, L.; Leonetti, M.; Le Goff, A.; Alarcon, K.; Neyton, J.; Bertrand, H. O.; Acher, F.; Paoletti, P. Structural basis of NR2B-selective antagonist recognition by N -methyl- d -aspartate receptors Mol. Pharmacol. 2009, 75, 60-74
11. Mony, L.; Kew, J. N.; Gunthorpe, M. J.; Paoletti, P. Allosteric modulators of NR2B-containing NMDA receptors: molecular mechanisms and therapeutic potential Br. J. Pharmacol. 2009, 157, 1301-1317
12. Carter, C.; Benavides, J.; Legendre, P.; Vincent, J. D.; Noel, F.; Thuret, F.; Lloyd, K. G.; Arbilla, S.; Zivkovic, B.; MacKenzie, E. T. Ifenprodil and SL 82.0715 as cerebral anti-ischemic agents. II. Evidence for N -methyl- d -aspartate receptor antagonist properties J. Pharmacol. Exp. Ther. 1988, 247, 1222-1232
13. Fischer, G.; Mutel, V.; Trube, G.; Malherbe, P.; Kew, J. N.; Mohacsi, E.; Heitz, M. P.; Kemp, J. A. Ro 25-6981, a highly potent and selective blocker of N -methyl- d -aspartate receptors containing the NR2B subunit. Characterization in vitro J. Pharmacol. Exp. Ther. 1997, 283, 1285-1292
14. Chenard, B. L.; Bordner, J.; Butler, T. W.; Chambers, L. K.; Collins, M. A.; De Costa, D. L.; Ducat, M. F.; Dumont, M. L.; Fox, C. B.; Mena, E. E. (1 S,2 S)-1-(4-Hydroxyphenyl)-2-(4-hydroxy-4-phenylpiperidino)-1-propanol: a potent new neuroprotectant which blocks N -methyl- d -aspartate responses J. Med. Chem. 1995, 38, 3138-3145
15. Beinat, C.; Banister, S.; Moussa, I.; Reynolds, A. J.; McErlean, C. S.; Kassiou, M. Insights into structure-activity relationships and CNS therapeutic applications of NR2B selective antagonists Curr. Med. Chem. 2010, 17, 4166-4190
16. Preskorn, S. H.; Baker, B.; Kolluri, S.; Menniti, F. S.; Krams, M.; Landen, J. W. An innovative design to establish proof of concept of the antidepressant effects of the NR2B subunit selective N -methyl- d -aspartate antagonist, CP-101,606, in patients with treatment-refractory major depressive disorder J. Clin. Psychopharmacol. 2008, 28, 631-637
17. Skolnick, P.; Popik, P.; Trullas, R. Glutamate-based antidepressants: 20 years on Trends Pharmacol. Sci. 2009, 30, 563-569
18. Gitto, R.; De Luca, L.; Ferro, S.; Citraro, R.; De Sarro, G.; Costa, L.; Ciranna, L.; Chimirri, A. Development of 3-substituted-1 H -indole derivatives as NR2B/NMDA receptor antagonists Bioorg. Med. Chem. 2009, 17, 1640-1647
19. Chimirri, A.; De Luca, L.; Ferro, S.; De Sarro, G.; Ciranna, L.; Gitto, R. Combined strategies for the discovery of ionotropic glutamate receptor antagonists ChemMedChem 2009, 4, 917-922
20. Gitto, R.; De Luca, L.; Ferro, S.; Occhiuto, F.; Samperi, S.; De Sarro, G.; Russo, E.; Ciranna, L.; Costa, L.; Chimirri, A. Computational studies to discover a new NR2B/NMDA receptor antagonist and evaluation of pharmacological profile ChemMedChem 2008, 3, 1539-1548
21. Gitto, R.; De Luca, L.; Ferro, S.; Buemi, M. R.; Russo, E.; De Sarro, G.; Costa, L.; Ciranna, L.; Prezzavento, O.; Arena, E.; Ronsisvalle, S.; Bruno, G.; Chimirri, A. Synthesis and biological characterization of 3-substituted-1 H -indoles as ligands of GluN2B-containing N -methyl- d -aspartate receptors J. Med. Chem. 2011, 54, 8702-8706
22. Karakas, E.; Simorowski, N.; Furukawa, H. Subunit arrangement and phenylethanolamine binding in GluN1/GluN2B NMDA receptors Nature 2011, 475, 249-253
23. Burger, P. B.; Yuan, H.; Karakas, E.; Geballe, M.; Furukawa, H.; Liotta, D. C.; Snyder, J. P.; Traynelis, S. F. Mapping the binding of GluN2B-selective NMDA receptor negative allosteric modulators Mol. Pharmacol. 2012, 82, 344-359
24. Ricerca Biosciences. http://www.ricerca.com.
25. Bembenek, S. D.; Tounge, B. A.; Reynolds, C. H. Ligand efficiency and fragment-based drug discovery Drug Discovery Today 2009, 14, 278-283
26. Reynolds, C. H.; Tounge, B. A.; Bembenek, S. D. Ligand binding efficiency: trends, physical basis, and implications J. Med. Chem. 2008, 51, 2432-2438
27. Leeson, P. D.; Springthorpe, B. The influence of drug-like concepts on decision-making in medicinal chemistry Nat. Rev. Drug Discovery 2007, 6, 881-890
28. ACD/Labs, version 8.0; Advanced Chemistry Development, Inc.: Toronto, Ontario, Canada, 2004; www.acdlabs.com/.
29. Perola, E. An analysis of the binding efficiencies of drugs and their leads in successful drug discovery programs J. Med. Chem. 2010, 53, 2986-2997
30. Nicholls, A.; McGaughey, G. B.; Sheridan, R. P.; Good, A. C.; Warren, G.; Mathieu, M.; Muchmore, S. W.; Brown, S. P.; Grant, J. A.; Haigh, J. A.; Nevins, N.; Jain, A. N.; Kelley, B. Molecular shape and medicinal chemistry: a perspective J. Med. Chem. 2010, 53, 3862-3886
31. Moussa, I. A.; Banister, S. D.; Beinat, C.; Giboureau, N.; Reynolds, A. J.; Kassiou, M. Design, synthesis, and structure-affinity relationships of regioisomeric N -benzyl alkyl ether piperazine derivatives as sigma-1 receptor ligands J. Med. Chem. 2010, 53, 6228-6239
32. Loftis, J. M.; Janowsky, A. The N -methyl- d -aspartate receptor subunit NR2B: localization, functional properties, regulation, and clinical implications Pharmacol. Ther. 2003, 97, 55-85
33. Zhang, X. X.; Bunney, B. S.; Shi, W. X. Enhancement of NMDA-induced current by the putative NR2B selective antagonist ifenprodil Synapse 2000, 37, 56-63
34. Zhang, X. X.; Shi, W. X. Dynamic modulation of NMDA-induced responses by ifenprodil in rat prefrontal cortex Synapse 2001, 39, 313-318
35. de Sarro, G.; Chimirri, A.; De Sarro, A.; Gitto, R.; Grasso, S.; Giusti, P.; Chapman, A. G. GYKI 52466 and related 2,3-benzodiazepines as anticonvulsant agents in DBA/2 mice Eur. J. Pharmacol. 1995, 294, 411-422
36. Gitto, R.; De Luca, L.; De Grazia, S.; Chimirri, A. Glutamatergic neurotransmission as molecular target of new anticonvulsants Curr. Top. Med. Chem. 2012, 12, 971-993
37. Molinspiration Cheminformatics. Cheminformatics on the Web. http://www.molinspiration.com/ (Molinspiration property engine, 2012).
38. Alavijeh, M. S.; Chishty, M.; Qaiser, M. Z.; Palmer, A. M. Drug metabolism and pharmacokinetics, the blood-brain barrier, and central nervous system drug discovery NeuroRx 2005, 2, 554-571
39. Pajouhesh, H.; Lenz, G. R. Medicinal chemical properties of successful central nervous system drugs NeuroRx 2005, 2, 541-553
40. The PyMOL Molecular Graphics System; Schrodinger, LLC: New York.
41. 3H] ifenprodil, a novel NMDA antagonist, to a polyamine-sensitive site in the rat cerebral cortex Eur. J. Pharmacol. 1990, 176, 249-250
42. Costa, L.; Trovato, C.; Musumeci, S. A.; Catania, M. V.; Ciranna, L. 5-HT(1A) and 5-HT(7) receptors differently modulate AMPA receptor-mediated hippocampal synaptic transmission Hippocampus 2012, 22, 790-801
43. Discovery Studio, version 2.5; Accelrys Software, Inc.: San Diego, CA, 2009.
44. Pedretti, A.; Villa, L.; Vistoli, G. VEGA: a versatile program to convert, handle and visualize molecular structure on Windows-based PCs J. Mol. Graphics Modell. 2002, 21, 47-49
45. Jones, G.; Willett, P.; Glen, R. C.; Leach, A. R.; Taylor, R. Development and validation of a genetic algorithm for flexible docking J. Mol. Biol. 1997, 267, 727-748