Synthesis and structure-activity relationship studies for hydantoins and analogues as voltage-gated sodium channel ligands

Journal of Medicinal Chemistry

Volumn 47, Issue 26, 2004, Pages 6519-6528

  Zha, Congxiang ^a   Brown, George B ^a   Brouillette, Wayne J ^a  

^a UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA HYDROXYAMIDE DERIVATIVE; AMIDE; AMINO ACID; BATRACHOTOXIN; BATRACHOTOXININ H 3; HYDANTOIN DERIVATIVE; HYDROXYACID; LIGAND; OXAZOLIDINEDIONE DERIVATIVE; SODIUM CHANNEL; UNCLASSIFIED DRUG; VOLTAGE GATED SODIUM CHANNEL;

ARTICLE; BINDING AFFINITY; BINDING ASSAY; CONCENTRATION RESPONSE; HYDROPHOBICITY; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; SYNAPTIC TRANSMISSION; SYNTHESIS;

ANIMALS; CEREBRAL CORTEX; HYDANTOINS; HYDROPHOBICITY; ION CHANNEL GATING; LIGANDS; MODELS, MOLECULAR; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RADIOLIGAND ASSAY; RATS; SODIUM CHANNELS; SYNAPTOSOMES;

EID: 10644294653     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm040077o     Document Type: Article

References (52)

1. + Channels: A Rational and Effective Strategy Against Ischemic Brain Damage. Pharmacol. Rev. 1996, 48, 21-67.
2. Hille, B. Ionic Channels of Excitable Membranes; Sinauer Associates: Sunderland, MA, 1991.
3. Catteral, W. A. Molecular Properties of Sodium and Calcium Channels. J. Bioenerg. Biomembr. 1996, 28 (3), 219-30.
4. Catteral, W. A. Structure and Function of Voltage-Sensitive Ion Channels. Annu. Rev. Biochem. 1995, 64, 493-531.
5. Catteral, W. A. Structure and Function of Voltage-Sensitive Ion Channels. Science 1988, 242, 50-61.
6. Catterall, W. A. Molecular Mechanisms of Gating and Drug Block of Sodium Channels. Novartis Found. Symp. 2002, 241, 206-18.
7. Wood, J. N.; Baker, M. Voltage-gated Sodium Channels. Curr. Opin. Pharmacol. 2001, 1 (1), 17-21.
8. Yu, F. H.; Catterall, W. A. Overview of the Voltage-gated Sodium Channel Family. Genome Biol. 2003, 4 (3), 207.
9. Taylor, C. P.; Narasimhan, L. S. Sodium Channels and Therapy of Central Nerve System Diseases. Adv. Pharmacol. 1997, 39, 447-98.
10. Yao, C.; Williams, A. J.; Lu, X. C.; Price, R. A.; Cunningham, B. S.; Berti, R.; Tortella, F. C.; Dave, J. R. The Sodium Channel Blocker RS 100642 Reverses Down-regulation of the Sodium Channel Alpha-subunit Na(v) 1.1 Expression Caused by Transient Ischemic Brain Injury in Rats. Neurotoxic. Res. 2003, 5 (4), 245-54.
11. 2+ Channels, and GABA (A) Receptors. Br. J. Anaesth. 2003, 9 (2), 199-211.
12. Kohling, R. Voltage-gated Sodium Channels in Epilepsy. Epilepsia 2002, 43 (11), 1278-95.
13. Vamecq, J.; Lambert, D.; Poupaart, J. H.; Masereel, B.; Stables, J. P. Anticonvulsant Activity and Interactions with Neuronal Voltage-dependent Sodium Channel of Analogues of Ameltolide. J. Med. Chem. 1998, 41 (18), 3307-13.
14. Cosford, N. D.; Meinke, P. T.; Stauderman, K. A.; Hess, S. D. Recent Advances in the Modulation of Voltage-gated Ion Channels for the Treatment of Epilepsy. Curr. Drug Targets: CNS Neurol. Disord. 2002, 1 (1), 81-104.
15. Ragsdale, D. S.; Avoli, M. Sodium Channels as Molecular Targets for Antiepileptic Drugs. Brain Res. Rev. 1998, 26, 16-28.
16. Campell, T. J.; Williams, K. M. Therapeutic Drug Monitoring: Antiarrhythmic Drugs. Br. J. Clin. Pharmacol. 1998, 46 (4), 307-49.
17. 3H] Batrachotoxinin Binding to Rat Cardiac Sodium Channels. J. Pharmacol. Exp. Ther. 1994, 268 (1), 187-94.
18. Sheldon, R. S.; Cannon, N. J.; Duff, H. J. A Receptor for Type I Antiarrhythmic Drugs Associated with Rat Cardiac Channels. Circ. Res. 1987, 61 (4), 492-7.
19. Catterall W. A. Inhibition of Voltage-sensitive Sodium Channels in Neuroblastoma Cells by Antiarrhythmic Drugs. Mol. Pharmacol. 1981, 20, 356-62.
20. 3H]Batrachotoxinin A 20-α-Benzoate Binding to Voltage-Sensitive Sodium Channels: A Rapid and Quantitative Assay for Local Anesthetic Activity in a Variety of Drugs. J. Med. Chem. 1985, 28, 381-8.
21. 3H]Batrachotoxinin-A 20α-Benzoate Binding in a Vesicular Preparation from Guinea Pig Cerebral Cortex. Inhibition by Local Anesthetics. Mol. Pharmacol. 1983, 23, 350-8.
22. Klamt, J. G. Effects of Intrathecally Administrated Lamotrigine, a Glutamate Release Inhibitor, on Short- and Long-Term Models of Hyperalgesia in Rats. Anesthesiology 1998, 88 (2), 487-94.
23. di Vadi, P. P.; Hamann, W. The Use of Lamotrigine in Neuropathic Pain. Anaesthesia 1998, 53 (80), 808-9.
24. Deffois, A.; Fage, D.; Carter, C. Inhibition of Synaptosomal Veratridine-induced Sodium Influx by Antidepressants and Neuroleptics Used in Chronic Pain. Neurosci. Lett. 1996, 220, 117-20.
25. Waxman, S. G.; Cummins, T. R.; Dib-Hall, S.; Fjell, J.; Black, J. A. Sodium Channels, Excitability of Primary Sensory Neurons, and the Molecular Basis of Pain. Muscle Nerve 1999, 22, 1177-87.
26. Melena, J.; Chidlow, G.; Osborne, N. N. Blockade of Voltage-sensitive Na+ Channels by the 5-HT (1A) Receptor Agonist 8-OH-DPAT: Possible Significance for Neuroprotection. Eur. J. Pharmacol. 2000, 406 (3), 319-24.
27. Waxman, S. G. Acquired Channelopathies in Nerve Injury and MS. Neurology 2001, 236 (1), 5-16.
28. Waxman, S. G.; Cummins, T. R.; Dib-hajj, S. D.; Black, J. A. Voltage-gated Sodium Channels and the Molecular Pathogenesis of Pain: a Review. J. Rehabil. Res. Dev. 2000, 37 (5), 517-28.
29. Deffois, A.; Fage, D.; Carter, C. Inhibition of Synaptosomal Veratridine-Induced Sodium Influx by Antidepressants and Neuroleptics Used in Chronic Pain. Neurosci. Lett. 1996, 220 (2), 117-20.
30. Li, H.-L.; Galue, A.; Meadows, L.; Ragsdale, D. S. A Molecular Basis for the Different Local Anesthetic Affinities of Resting Versus Open and Inactivated States of the Sodium Channel. Mol. Pharmacol. 1999, 55 (1), 134-41.
31. + Channels. Proc. Natl. Acad. Sci. U.S.A. 1998, 93, 9270-5.
32. + Channels: Local Anesthetics, Antiarrhythmics and Anticonvulsants. Trends Pharmacol. Sci. 1987, 8, 57-65.
33. + Channels by Local Anesthetics. Science 1994, 265, 1724-8.
34. + Channel. Proc. Natl. Acad. Sci. U.S.A. 1995, 92 (5), 11839-43.
35. De Leon, L.; Ragsdale, D. S. State-dependent Access to the Batrachotoxin Receptor on the Sodium Channel. NeuroReport 2003, 14 (10), 1353-6.
36. Courtney, K. R. Structure-Activity Relations for Frequency Dependent Sodium Channel Block in Nerve by Local Anesthetics. J. Pharmacol. Exp. Ther. 1980, 213 (1), 114-9.
37. Liu, G.; Yarov-Yarovoy, V.; Nobbs, M.; Clare, J. J.; Scheuer, T.; Catterall, W. A. Differential Interactions of Lamotrigine and Related Drugs with Transmembrane Segment IVS6 of Voltage-gated Sodium Channels. Neuropharmacology 2003, 44, 413-22.
38. (a) Khodorov, B. I. Sodium Inactivation and Drug-Induced Immobilization of the Gating Charge in Nerve Membrane. Prog. Biophys. Mol. Biol. 1981, 37, 49-89.
39. (b) Unverferth, K.; Engel, J.; Höfgen, N.; Rostock, A.; Günther, R.; Lankau, H.-J.; Menzer, M.; Rolfs, A.; Liebscher, J.; Müller, B.; Hofmann, H.-J. Synthesis, Anticonvulsant Activity, and Structure-Activity Relationships of Sodium Channel Blocking 3-Aminopyrroles. J. Med. Chem. 1998, 41, 63-73.
40. Roufos, I.; Hays, S. J.; Dooley, D. J.; Schwarz, R. D.; Campbell, G. W.; Probert, A. W. Synthesis and Pharmacological Evaluation of Phenylacetamides as Sodium-Channel Blockers. J. Med. Chem. 1994, 37, 268-74.
41. Roufos, I.; Hays, S. J.; Dooley, D. J.; Schwarz, R. D. A Structure-Activity Relationship Study of Novel Phenylacetamides Which Are Sodium Channel Blockers. J. Med. Chem. 1996, 39, 1514-20.
42. De Luca, A.; Talon, S.; De Bellis, M.; Desaphy, J.-F.; Lentini, G.; Corbo, F.; Scilimati, A.; Franchini, C.; Tortorella, V. Optimal Requirements for High Affinity and Use-Dependent Block of Skeletal Muscle Sodium Channel by N-Benzyl Analogs of Tocainide-Like Compounds. Mol. Pharmacol. 2003, 64, 932-45 and references therein.
43. Cestele, S.; Catterall, W. A. Molecular Mechanisms of Neurotoxin Action on Voltage-Gated Sodium Channels. Biochimie 2000, 82, 883-92.
44. Grauert, M.; Bechtel, W. D.; Weiser, T.; Werner, S.; Nar, H.; Carter, A. J. Synthesis and Structure-Activity Relationships of 6,7-Benzomorphan Derivatives as Use-Dependent Sodium Channel Blockers for the Treatment of Stroke. J. Med. Chem. 2002, 45, 3755-64.
45. Leong, D.; Bloomquist, J. R.; Bempong, J.; Dybas, J. A.; Kinne, L. P.; Lyga, J. W.; Marek, F. L.; Nicholson, R. A. Insecticidal Arylalkylbenzhydrolpiperidines: Novel Inhibitors of Voltage-Sensitive Sodium and Calcium Channels in Mammalian Brain. Pest Manage. Sci. 2001, 57, 889-95.
46. Nicholson, R. A.; Liao, C.; Zheng, J.; David, L. S.; Coyne, L.; Errington, A. C.; Singh, G.; Lees, G. Sodium Channel Inhibition by Anandamide and Synthetic Cannabimimetics in Brain. Brain Res. 2003, 978, 194-204.
47. Anger, T.; Madge, D. J.; Mulla, M.; Riddall, D. Medicinal Chemistry of Neuronal Voltage-Gated Sodium Channels. J. Med. Chem. 2001, 44, 115-37.
48. Meza-Toledo, S. E.; Zenteno-Garcia, M. T.; Juarez-Carvajal, E.; Martinez-Munoz, D.; Carvajal-Sandoval, G. A. New Homologous Series of Anticonvulsants: Phenyl Alcohol Amides. Arzneim-Forsch. 1990, 40 (11), 1289-90.
49. Brown, M. L.; Zha, C. C.; Van Dyke, C. C.; Brown, G. B.; Brouillette, W. J. Comparative Molecular Field Analysis of Hydantoin Binding to the Neuronal Voltage-Dependent Sodium Channel. J. Med. Chem. 1999, 42, 1537-45.
50. Brown, M. L.; Brown, G. B.; Brouillette, W. J. Effects of log P and Phenyl Ring Conformation on the Binding of 5-Phenylhydantoms to the Voltage-Dependent Sodium Channel. J. Med. Chem. 1997, 40, 602-7.
51. Basavaiah, D.; Krishna, P. R. New Cyclohexyl-Based Chiral Auxiliaries: Enantioselective Synthesis of α-Hydroxy Acids. Tetrahedron 1995, 51 (44), 12169-12218.
52. Brouillette, W. J.; Brown, G. B.; Delorey, T. M.; Shirali, S. S.; Grunewald, G. L. Anticonvulsant Activities of Phenyl-Substituted Bicyclic 2,4-Oxazolidinediones and Monocyclic Models. Comparison with Binding to the Neuronal Voltage-Dependent Sodium Channel. J. Med. Chem. 1988, 31, 2218-21.