1-aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: Novel AMPA receptor antagonists

Journal of Medicinal Chemistry

Volumn 40, Issue 8, 1997, Pages 1258-1269

  Chimirri, Alba ^a   De Sarro, Giovambattista ^b   De Sarro, Angela ^a   Gitto, Rosaria ^a   Grasso, Silvana ^a   Quartarone, Silvana ^a   Zappalà, Maria ^a   Giusti, Piero ^c   Libri, Vincenzo ^d,e   Constanti, Andrew ^e   Chapman, Astrid G ^f  

^a UNIVERSITY OF MESSINA   (Italy)

^b UNIVERSITY MEDITERRANEA OF REGGIO CALABRIA   (Italy)

^c UNIVERSITY OF PADOVA   (Italy)

^d UNIVERSITY OF ROME TOR VERGATA   (Italy)

^e UNIVERSITY OF LONDON   (United Kingdom)

^f KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 AMINOPHENYL) 4 METHYL 7,8 METHYLENEDIOXY 5H 2,3 BENZODIAZEPINE; AMPA RECEPTOR; AMPA RECEPTOR ANTAGONIST; ANIRACETAM; ANTICONVULSIVE AGENT; BENZODIAZEPINE RECEPTOR; FLUMAZENIL; GLUTAMATE RECEPTOR; N METHYL DEXTRO ASPARTIC ACID RECEPTOR;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTICONVULSANT ACTIVITY; ARTICLE; AUDITORY STIMULATION; CONTROLLED STUDY; DOSE RESPONSE; DRUG POTENCY; DRUG SYNTHESIS; FEMALE; GUINEA PIG; INTRACEREBROVENTRICULAR DRUG ADMINISTRATION; INTRAPERITONEAL DRUG ADMINISTRATION; MALE; MEMBRANE CURRENT; MOUSE; NONHUMAN; RECEPTOR BLOCKING; SEIZURE SUSCEPTIBILITY; STRUCTURE ACTIVITY RELATION;

ACOUSTIC STIMULATION; ALPHA-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID; ANIMALS; ANTICONVULSANTS; BENZODIAZEPINONES; CONVULSANTS; MICE; MICE, INBRED DBA; PENTYLENETETRAZOLE; PYRROLIDINONES; RECEPTORS, AMPA; SEIZURES;

EID: 14444267762     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960506l     Document Type: Article

References (63)

1. 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.
2. Saxena, A. K.; Saxena, M. Developments in Anticonvulsants. Prog. Drug Res. 1995, 44, 185-291.
3. (a) Krogsgaard-Larsen, P. Amino Acid Receptors. In Comprehensive Medicinal Chemistry; Hansch, C., Ed.; Pergamon Press: Oxford, 1990; Vol. 3, pp 493-537.
4. (b) Desos, P.; Lespagnol, J. M.; Morain, P.; Lestage, P.; Cordi, A. A. Structure-Activity Relationships in a Series of 2(1H)-Quinolones Bearing Different Acidic Function in the 3-Position: 6,7-Dichloro-2(1H)-oxoquinoline-3-phosphonic Acid, a New Potent and Selective AMPA/ Kainate Antagonist with Neuroprotective Properties. J. Med. Chem. 1996, 39, 197-206.
5. Rogawski, M. A. The NMDA Receptor, NMDA Antagonists And Epilepsy Therapy. Drugs 1992, 44, 279-292.
6. Ohmori, J.; Sakamoto, S.; Kubota, H.; Shimizu-Sasamata, M.; Okada, M.; Kawasaki, S.; Nikada, K.; Togami, J.; Furuya, T.; Murase, K. 6-(1H-Imidazol-1-yl)-7-nitro-2,3(1H,4H)-quinoxalinedione Hydrochloride (YM90K) and Related Compounds: Structure-Activity Relationships for the AMPA-Type Non-NMDA Receptor. J. Med. Chem. 1994, 37, 467-475.
7. Chapman, A. G.; Smith, S. E.; Meldrum, B. S. The Anticonvulsant Effect of the Non-NMDA Antagonists, NBQX and GYKI 52466 in Mice. Epilepsy Res. 1991, 9, 92-96.
8. De Sarro, G. B.; Ongini, E.; Bertorelli, R.; Aguglia, U.; De Sarra, A. Excitatory Amino Acid Neurotransmission through both NMDA and Non-NMDA Receptors is involved in the Anticonvulsant Activity of Felbamate in DBA/2 Mice. Eur. J. Pharmacol. 1994, 262, 11-19.
9. Tarnawa, I.; Parkas, S.; Berzsenyi, P.; Pataki, A.; Andrasi, F. Electrophysiological Studies with a 2,3-Benzodiazepine Muscle Relaxant: GYKI 52466. Eur. J. Pharmacol. 1989, 67, 193-199.
10. (a) Chimirri, A.; De Sarro, A.; De Sarro, G. B.; Grasso, S.; Trimarchi, G. R.; Zappalà, M. Synthesis and Anticonvulsant Properties of 2,3,3a,4-Tetrahydro-1H-pyrrolo[1,2-α]benzimidazol-1-ones. J. Med. Chem. 1989, 32, 93-95.
11. (b) Chimirri, A.; Grasso, S.; Monforte, A. M.; Zappalà, M.; De Sarro, A.; De Sarro, G. B. Synthesis and Anticonvulsant Properties of 3-(1,3,4-Thiadiazol-2-yl)thiazolidin-4-ones. Il Farmaco 1991, 46, 935-943.
12. (c) De Sarro, A.; De Sarro, G. B.; Chimirri, A.; Grasso, S.; Monforte, A. M.; Zappalà, M. Anticonvulsant Activity of Pyrrolo-[1′ ,2′:1,2]imidazo[4,5-b]pyridines, Pyrrolo[2′ ,1′:2,3]imidazo[4,5-c]pyridines and Pyrrolo[2, 1-f]purines in DBA/2 Mice. Gen. Pharmacol. 1994, 25, 1027-1031.
13. (a) De Sarro, G. B.; Zappalà, M.; Grasso, S.; Chimirri, A.; Spagnolo, C.; De Sarro, A. Molecular Requirement for Anticonvulsant Activity in a Series of 1,5-Benzodiazepines and [1,2,4]-Oxadiazolo[4,5-α][1,5]benzodiazepine Derivatives. Mol. Neuropharmacol. 1992, 1, 195-202.
14. (b) De Sarro, G. B.; Zappalà, M.; Grasso, S.; Chimirri, A.; De Sarro, A. Molecular Requirement for Anticonvulsant Activity in a Series of Thiazolo-1,4-benzodiazepines and Comparison with Classical Benzodiazepines. Gen. Pharmacol. 1993, 24, 877-884.
15. (a) De Sarro, G.; Chimirri, A.; De Sarro, A.; Gitto, R.; Grasso, S.; Zappalà, M. 5H-[1,2,4]Oxadiazolo[5,4-d][1,5]benzothiazepines as Anticonvulsant Agents in DBA/2 Mice. Eur. J. Med. Chem. 1995, 30, 925-929.
16. (b) Chimirri, A.; Gitto, R.; Grasso, S.; Monforte, A. M.; Zappalà, M. Annelated-1,5-benzothiazepines. Adv. Heterocycl. Chem. 1995, 63, 61-101.
17. (a) Chapman, A. G.; Croucher, M. J.; Meldrum, B. S. Evaluation of Anticonvulsant Drugs in DBA/2 Mice with Sound-Induced Seizures. Arzneim. Forsch. 1984, 34, 1261-1264.
18. (b) Seyfried, T. N.; Glaser, G. H. A Review of Mouse Mutans as Genetic Models of Epilepsy. Epilepsia 1985, 26, 143-150.
19. (c) Engstrom, F. L.; Woodbury, D. M. Seizure Susceptibility in DBA/2 and C57 Mice: the Effects of Various Convulsants. Epilepsia 1988, 29, 389-395.
20. Pelletier, J. C.; Hesson, D. P.; Jones, K. A.; Costa, A. M. Substituted 1,2-Dihydrophthalazines: Potent, Selective, and Noncompetitive Inhibitors of the AMPA Receptor. J. Med Chem. 1996, 39, 343-346.
21. Ito, I.; Tanabe, S.; Kohda, A.; Sugiyama, H. Allosteric Potentiation of Quisqualate Receptors by Nootropic Drug Aniracetam. J. Physiol. (London) 1990, 424, 533-543.
22. Gatta, F.; Piazza, D.; Del Giudice, M. R.; Massotti, M. Derivatives of 2,3-Benzodiazepines. Il Farmaco Ed. Sc. 1985, 40, 942-955.
23. (a) Chapman, A. G.; De Sarro, G. B.; Premachandra, M.; Meldrum, B. S. Bidirectional Effects of β-Carbolines in Reflex Epilepsy. Brain Res. Bull. 1987, 19, 337-346.
24. (b) De Sarro, G. B.; Libri, V.; Ascioti, C.; Testa, R.; Nisticò, G. Anticonvulsant Effect of Denzimol in DBA/2 Mice. Neuropharmacology 1987, 26, 1425-1429.
25. (a) Honoré, T.; Davies, S. N.; Drejer, J.; Fletcher, E. J.; Jacobsen, P.; Lodge, D.; Nielsen, F. E. Quinoxalinediones: Potent Competitive non-NMDA Glutamate Receptor Antagonists. Science 1988, 241, 701-707.
26. 3H-CNQX Binds with Equal Affinity to two Agonist States of Quisqualate Receptor. Biochem. Pharmacol. 1989, 38, 3207-3212.
27. Chapman, A. G.; Al-Zubaidy, Z.; Meldrum, B. S. Aniracetam Reverses the Anticonvulsant Action of NBQX and GYKI 52466 in DBA/2 Mice. Eur. J. Pharmacol. 1993, 231, 301-303.
28. Bisga, A.; Krzascik, P.; Jankowska, E.; Palejko, W.; Kostowski, W.; Danysz, W. Effect of Glutamate Antagonists on NMDA-and AMPA-induced Convulsant Effects in Mice and Rats. Eur. J. Pharmacol. 1993, 242, 213-220.
29. Donevan, S. D.; Yamaguchi, S. I.; Rogawski, M. A. Non-N-methyl-D-aspartate Receptor Antagonism by 3-N-Substituted 2,3-Benzodiazepines: Relationship to Anticonvulsant Activity. J. Pharmacol. Exp. Ther. 1994, 271, 25-29.
30. Smith, S. E.; Durmuller, N.; Meldrum, B. S. The non-N-methyl-D-aspartate Receptor Antagonists, GYKI 52466 and NBQX are Anticonvulsant in two Animal Models of Reflex Epilepsy. Eur. J. Pharmacol. 1991, 201, 179-183.
31. Rogawski, M. A. Therapeutic Potential of Excitatory Amino Acid Antagonists: Channel Blockers and 2,3-Benzodiazepines. Trends Pharmacol. Sci. 1993, 14, 325-331.
32. Donevan, S. D.; Rogawski, M. A. GYKI 52466, a 2,3-Benzodiazepine, is a Highly Selective, Noncompetitive Antagonist of AMPA/Kainate Receptor Responses. Neuron 1993, 10, 51-59.
33. Zorumski, C. F.; Yamada, K. A.; Price, M. D.; Olney, J. W. Benzodiazepine Recognition Side Associated with non-NMDA Glutamate Receptor. Neuron 1993, 10, 61-67.
34. Lodge, D.; Bond, A.; Birds, D.; Palmer, A. J. Interaction between 2,3-Benzodiazepine and Cyclothiazide on the AMPA Subtype of Glutamate Receptor. Neurosci. Abs. 1993, 19, 124.4.
35. Rammers, G.; Swandulla, D.; Collingridge, G. L.; Hartman, S.; Passons, C. G. Interaction of 2,3-Benzodiazepine and Cyelothiazide at AMPA Receptor: Patch Clamp Recordings in Cultured Neurones and Area CA1 in Hippocampal Slices. Br. J. Pharmacol. 1996, 117, 1209-1221.
36. (a) Chapman, A. G.; Meldrum, B. S. Epilepsy Prone Mice: Genetically Determined Sound-Induced Seizures. In Neurotransmitters and Epilepsy; Jobe, P. C., Laird, H. E., Eds.; The Humana Press: Clifton, NJ, 1987; pp 197-208.
37. (b) Chapman, A. G.; Meldrum, B. S. Non-competitive N-methyl-D-aspartate Antagonists Protect Against Sound-Induced Seizures in DBA/2 Mice. Eur. J. Pharmacol. 1989, 166, 201-211.
38. (c) De Sarro, G. B.; De Sarro, A. Anticonvulsant Activity of Competitive Antagonists of NMDA Receptor in Genetically Epilepsy Prone Rats. Eur. J. Pharmacol. 1992, 215, 221-229.
39. (d) De Sarro, G. B.; De Sarro, A. Anticonvulsant Properties of Non-Competitive Antagonists of NMDA Receptor in Genetically Epilepsy Prone Rats. Comparison with CPPene. Neuropharmacology 1993, 32, 51-58.
40. (e) McEntee, W. C.; Crook, T. H. Glutamate, its Role in Learning, Memory, and the Aging Brain. Psychopharmacology 1993, 111, 391-401.
41. (a) Chiamulera, C.; Costa, S.; Reggiani, A. Effect of NMDA-and Strychnine-Insensitive Glycine Site Antagonists on NMDA-Mediated Convulsions and Learning, Psychopharmacology 1990, 102, 551-552.
42. (b) Loescher, W. R.; Annies, R.; Honack, D. Comparison of Competitive and Uncompetitive NMDA Receptor Antagonist with Regard to Monoaminergic Neuronal Activity and Behavioural Effects in Rats. Eur. J. Pharmacol. 1993, 242, 263-274.
43. Meldrum, B.; Garthwaite, J. Excitatory Amino Neurotoxicity and Neurodegenerative Disease. Trends Pharmacol. Sci. 1990, 11, 379-387.
44. Buchan, A. M.; Lesiuk, H.; Barnes, K. A.; Li, H.; Huang, Z. G.; Smith, K. E.; Xue, D. AMPA Antagonists: Do They Hold More Promise for Clinical Stroke Trials than NMDA Antagonists? Stroke 1993, 24, suppl. I, 148-152.
45. (a) Boyce, C. B. C.; Milborrow, B. V. A Simple Assessment of Partition Data for Correlating Structure and Biological Activity Using Thin-Layer Chromatography. Nature 1965, 208, 537-539.
46. (b) Pietrogrande, M. C.; Borea, P. A.; Biagi, G. L. Lipophilicity Measurements of Benzodiazepine-Receptor Ligands by Reversed-Phase Liquid Chromatography. Comparison between High-Performance Liquid and Thin-Layer Chromatography. J. Chromatogr. 1988, 447, 404-409.
47. (c) Chimirri, A.; De Sarro, A.; De Sarro, G.; Grasso, S.; Trimarchi, G. R.; Zappalà, M. Synthesis and Anticonvulsant Properties of 2,3,3a,4-Tetrahydro1H-pyrrolo[1,2-a]benzimidazol-1-ones. J. Med. Chem. 1989, 32, 93-95.
48. (a) Hall, C. S. Genetic Differences in Fatal Audiogenic Seizures between two Inbred Strains of House Mice. J. Heredity 1947, 38, 2-6.
49. (b) Collins, R. L. Audiogenic Seizures. In Experimental Models of Epilepsy; Purpura, P., Penry, J. K., Tower, D., Woodbury, D. M., Walter, R., Eds.; Raven Press: New York, 1972; pp 347-372.
50. De Sarro, G. B.; Croucher, M. J.; Meldrum, B. S. Anticonvulsant Actions of DS 103-282; Pharmacological Studies in Rodents and the Baboon Papio papio. Neuropharmacology 1984, 23, 526-530.
51. Swinyard, E. A.; Brown, W. C.; Goodman, L. S. Comparative Assays of Antiepileptic in Mice and Rats. J. Pharmacol. Exp. Ther. 1952, 106, 319-330.
52. Swinyard, E. A.; Woodhead, J. M. Experimental Detection, Quantification and Evaluation of Anticonvulsants. In Epileptic Drugs; Woodbury, D. M., Penry, J. K., Pippenger, C. E., Eds.; Raven Press: New York, 1982; pp 111-126.
53. De Sarro, G. B.; Ongini, E.; Bertorelli, R.; Aguglia, U.; De Sarro, A. Excitatory Amino Acid Neurotransmission through both NMDA and Non-NMDA Receptors is Involved in the Anticonvulsant Activity of Felbamate in DBA/2 mice. Eur. J. Pharmacol. 1994, 262, 11-19.
54. (a) Apud, J. A.; Ito, Y. Semi-preparative Purification of an Endogenous Ligand for Brain Serotonin-2-receptor by Coil Planet Centrifuge Counter-Current Chromatography. J. Chromatogr. 1991, 538, 177-185.
55. (b) Bylund, D. B.; Yamamura, H. I. Methods for Receptor Binding. In Methods in Neurotransmitter Receptor Analysis; Yamamura, H. I.; Enna, S. J.; Kuhar, M. J., Eds.; Raven Press: New York, 1990; pp 1-35.
56. 3H]3-(2-Carboxypiperazin-4-yl)propyl-1-phosphonic acid to Rat Brain Membrane: a Selective High-Affinity Ligand for N-Methyl-D-aspartate Receptors, J. Pharmacol. Exp. Ther. 1987, 240, 778-784.
57. 3H]MK-801) in Rat Brain. J. Pharmacol. Exp. Ther. 1991, 256, 811-819.
58. 3H](R,S)-α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid Binding Sites. J. Neurochem. 1990, 54, 686-695.
59. Dunham, N. W.; Miya, T. S. A Note on a Simple Apparatus for Detecting Neurological Deficit in Rats and Mice. J. Am. Pharm. Assoc. 1957, 46, 208-209.
60. Constanti, A.; Bagetta, G.; Libri, V. Persistent Muscarinic Excitation in Guinea-Pig Olfactory Cortex Neurons: Involvement of a Slow Post-Stimulus Afterdepolarizing Current. Neuroscience 1993, 56, 887-904.
61. Libri, V.; Constanti, A.; Calaminici, M.; Nisticò, G. A Comparison of the Muscarinic Response and Morphological Properties of Identified Cells in the Guinea-pig Olfactory Cortex in vitro. Neuroscience 1994, 59, 331-347.
62. Litchfield, J. T.; Wilcoxon, F. A Simplified Method of Evaluating Dose-Effects Experiments. J. Pharmacol. Exp. Ther. 1949, 96, 99-113.
63. McPherson, G. I. Ligand (release 2.0), Elsevier Biosoft, Cambridge, 1987.