4H-1,2,4-Pyridothiadiazine 1,1-dioxides and 2,3-dihydro-4H-1,2,4-pyridothiadiazine 1,1-dioxides chemically related to diazoxide and cyclothiazide as powerful positive allosteric modulators of (R/S)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid receptors: design, synthesis, pharmacology and structure-activity relationships
Pirotte, Bernard; Podona, T.; Diouf, O.et al.
1998 • In Journal of Medicinal Chemistry, 41, p. 2946-2959
Pirotte, Bernard ; Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique
Podona, T.
Diouf, O.
De Tullio, Pascal ; Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique
Lebrun, P.
Dupont, L.
Somers, F.
Delarge, J.
Morain, P.
Lestage, P.
Lepagnol, J.
Spedding, M.
Language :
English
Title :
4H-1,2,4-Pyridothiadiazine 1,1-dioxides and 2,3-dihydro-4H-1,2,4-pyridothiadiazine 1,1-dioxides chemically related to diazoxide and cyclothiazide as powerful positive allosteric modulators of (R/S)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid receptors: design, synthesis, pharmacology and structure-activity relationships
Publication date :
1998
Journal title :
Journal of Medicinal Chemistry
ISSN :
0022-2623
eISSN :
1520-4804
Publisher :
American Chemical Society, Washington, United States - District of Columbia
Krogsgaard-Larsen, P.; Ebert, B.; Lund, T. M.; Bräuner-Osborne, H.; Sløk, F. A.; Johansen, T. N.; Brehm, L.; Madsen, U. Design of Excitatory Amino Acid Receptor Agonist, Partial Agonists and Antagonists: Ibotenic Acid as a Key Lead Structure. Eur. J. Med. Chem. 1996, 31, 515-537.
Krogsgaard-Larsen, P., Hansen, J. J., Eds. Excitatory Amino Acid Receptors. Design of Agonists and Antagonists; Ellis Horwood: Chichester, 1992.
Collingridge, G. L., Watkins, J. C., Eds. The NMDA Receptor; Oxford University Press: Oxford, 1994.
Wheal, H. V., Thomson, A. M., Eds. Excitatory Amino Acids and Synaptic Transmission; Academic Press: London, 1995.
Conn, P. J., Patel, J., Eds. The Metabotropic Glutamate Receptors; Humana Press: New Jersey, 1994.
Deutsch, S. I.; Mastropaolo, J.; Schwartz, B. L.; Rosse, R. B.; Morihisa, J. M. A "Glutamatergic Hypothesis" of Schizophrenia: Rationale for Pharmacotherapy with Glycine. Clin. Neuropharmacol. 1989, 12, 1-13.
Bowen, D. M. Treatment of Alzheimer's Disease. Molecular Pathology versus Neurotransmitter-based Therapy. Br. J. Psychiat. 1990, 157, 327-330.
Danysz, W.; Zajaczkowski, W.; Parsons, C. G. Modulation of Learning Processes by Ionotropic Glutamate Receptor Ligands. Behav. Pharmacol. 1995, 6, 455-474.
Weiss, J. H.; Choi, D. W. Differential Vulnerability to Excitatory Amino Acid-induced Toxicity and Selective Neuronal Loss in Neurodegenerative Diseases. Can. J. Neurol. Sci. 1991, 18, 394-397.
Choi, D. W. Non-NMDA Receptor-mediated Neuronal Injury in Alzheimer's Disease? Neurobiol. Aging 1989, 10, 605-606.
Rogawski, M. A. Therapeutic Potential of Excitatory Amino Acid Antagonists: Channel Blockers and 2,3-Benzodiazepines. Trends Pharmacol. Sci. 1993, 14, 325-331.
Yamada, K. A.; Tang, C. M. Benzothiadiazides Inhibit Rapid Glutamate Receptor Desensitization and Enhance Glutamatergic Synaptic Currents. J. Neurosci. 1993, 13, 3904-3915.
Zorumski, C. F.; Yamada, K. A.; Price, M. T.; Olney; J. W. A Benzodiazepine Recognition Site Associated with the Non-NMDA Glutamate Receptor. Neuron 1993, 10, 61-67.
Isaacson, J. S.; Nicoll, R. A. Aniracetam Reduces Glutamate Receptor Desensitization and Slows the Decay of Fast Excitatory Synaptic Currents in the Hippocampus. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 10936-10940.
Tang, C. M.; Shi, Q. Y.; Katchman, A.; Lynch, G. Modulation of the Time Course of Fast EPSCs and Glutamate Channel Kinetics by Aniracetam. Science 1991, 254, 288-290.
Yamada, K. A.; Rothman, S. M. Diazoxide Blocks Glutamate Desensitization and Prolongs Excitatory Postsynaptic Currents in Rat Hippocampal Neurons. J. Physiol. (London) 1992, 458, 385-407.
Randle, J. C. R.; Biton, C.; Lepagnol, J. M. Allosteric Potentiation by Diazoxide of AMPA Receptor Currents and Synaptic Potentials. Eur. J. Pharmacol. - Mol. Pharmacol. Sect. 1993, 247, 257-265.
Partin, K. M.; Mayer, M. L. Negative Allosteric Modulation of Wild-type and Mutant AMPA Receptors by GYKI 53655. Mol. Pharmacol. 1996, 49, 142-148.
Kessler, M.; Arai, A.; Quan, A.; Lynch, G. Effect of Cyclothiazide on Binding Properties of AMPA-type Glutamate Receptors: Lack of Competition between Cyclothiazide and GYKI 52466. Mol. Pharmacol. 1996, 49, 123-131.
Desai, M. A.; Burnett, J. P.; Ornstein, P. L.; Schoepp, D. D. Cyclothiazide Acts at a Site on the Alpha-amino-3-hydroxy-5-methyl-4-isoxazole Propionic Acid Receptor Complex that Does not Recognize Competitive or Noncompetitive AMPA Receptor Antagonists. J. Pharmacol Exp. Ther. 1995, 272, 38-43.
Granger, R.; Staubli, U.; Davis, M.; Perez, Y.; Nilsson, L.; Rogers, G. A.; Lynch, G. A. Drug that Facilitates Glutamatergic Transmission Reduces Exploratory Activity and Improves Performance in a Learning-Dependent Task. Synapse 1993, 15, 326-329.
Desai, M. A.; Valli, M. J.; Monn, J. A.; Schoepp, D. D. 1-BCP, A Memory-enhancing Agent, Selectivity Potentiates AMPA-induced [3H]Norepinephrine Release in Rat Hippocampal Slices. Neurpharmacology 1995, 34, 141-147.
Larson, J.; Lieu, T.; Petchpradub, V.; Leduc, B.; Ngo, H.; Rogers, G. A.; Lynch, G. Facilitation of Olfactory Learning by a Modulator of AMPA Receptors. J. Neurosci. 1995, 15, 8023-8030.
Arai, A.; Kessler, M.; Rogers, G.; Lynch, G. Effects of a Memory-enhancing Drug on DL-Alpha-amin-3-hydroxy-5-methyl-4-isoxazolepropionic Acid Receptor Currents and Synaptic Transmission in Hippocampus. J. Pharmacol. Exp. Ther. 1996, 278, 627-638.
Straubli, U.; Rogers, G.; Lynch, G. Facilitation of Glutamate Receptors Enhances Memory. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 777-781.
Staubli, U.; Perez, Y.; Xu, F. B.; Rogers, G.; Ingvar, M.; Stone-Elander, S.; Lynch, G. Centrally Active Modulators of Glutamate Receptors Facilitate the Induction of Long-term Potentiation in Vivo. Proc. Natl. Acad. U.S.A. 1994, 97, 11158-11162.
Shors, T. J.; Servatius, R. J.; Thompson, R. F.; Rogers, G.; Lynch, G. Enhanced Glutamatergic Neurotransmission Facilitates Classical Conditioning in the Freely Moving Rat. Neurosci. Lett. 1995, 186, 153-156.
Arai, A.; Kessler, M.; Xiao, P.; Ambros-Ingerson, J.; Rogers, G.; Lynch, G. A centrally Active Drug that Modulates AMPA Receptor Gated Currents. Brain Res. 1994, 638, 343-346.
Yamada, K. A.; Tang, C. M. Benzothiadiazides Inhibit Rapid Glutamate Receptor Desensitization and Enhance Glutamatergic Synaptic Currents. J. Neurosci. 1993, 13, 3904-3915.
Bertolino, M.; Baraldi, M.; Parenti, C.; Braghiroli, D.; DiBella, Maria; Vicini, S.; Costa, E. Modulation of AMPA/Kainate Receptors by Analogues of Diazoxide and Cyclothiazide in Thin Slices of Rat Hippocampus. Receptors Channels 1993, 1, 267-278.
Uzunov, D. P.; Zivkovich, I.; Pirkle, W. H.; Costa, E.; Guidotti, A. Enantiomeric Resolution With a New Chiral Stationary Phase of 7-Chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine S, S-dioxide, a Cognition-enhancing Benzothiadiazine Derivative. J J. Pharm. Sci. 1995, 84, 937-942.
Thompson, D. M.; Guidotti, A.; DiBella, M.; Costa, E. 7-Chloro- 3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine S, S-dioxide (IDRA 21), a Congener of Aniracetam, Potently Abates Pharmacologically Induced Cognitive Impairments in Patas Monkeys. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 7667-7671.
Zivkovic, I.; Thompson, D. M.; Bertolino, M.; Uzunov, D.; DiBella, M.; Costa, E.; Guidotti, A. 7-Chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine S, S-dioxide (IDRA 21): a Benzothiadiazine Derivative that Enhances Cognition by Attenuating DL-Alpha-amino-2,3-dihydro-5-methyl-3-oxo-4-isoxazolepropanoic acid (AMPA) receptor Desensitization. J. Pharmacol. Exp. Ther. 1995, 272, 300-309.
Pirotte, B.; de Tullio, P.; Lebrun, P.; Antoine, M.-H.; Fontaine, J.; Masereel, B.; Schynts, M.; Dupont, L.; Herchuelz, A.; Delarge, J. 3-(Alkylamino)-4H-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-Dioxides as powerful Inhibitors of Insulin Release from Rat Pancreatic B-Cells: a New Class of Potassium Channel Openers? J. Med. Chem. 1993, 36, 3211-3213.
Pirotte, B.; Antoine, M.-H.; de Tullio, P.; Hermann, M.; Herchuelz, A.; Delarge, J.; Lebrun, P. A Pyridothiadiazine (BPDZ44) as a New and Potent Activator of ATP-Sensitive K+ Channels. Biochem. Pharmacol. 1994, 47, 1381-1386.
de Tullio, P.; Pirotte, B.; Lebrun, P.; Fontaine, J.; Dupont, L.; Antoine, M.-H.; Ouedraogo, R.; Khelili, S.; Maggetto, C.; Masereel, B.; Diouf, O.; Podona, T.; Delarge, J. 3- and 4-Substituted 4H-Pyrido[4,3-e]-1,2,4-thiadiazine 1,1-Dioxides as Potassium Channel Openers: Synthesis, Pharmacological Evaluation, and Structure-activity Relationships. J. Med. Chem. 1996, 39, 937-948.
de Tullio, P.; Pirotte, B.; Dupont, L.; Masereel, B.; Laeckmann, D.; Podona, T.; Diouf, O.; Lebrun, P.; Delarge, J. Synthesis and Structural Studies of a New Class of Heterocyclic Compounds: 1,2,4-Pyridothiadiazine 1,1-Dioxides, Pyridyl Analogues of 1,2,4-Benzothiadiazine 1,1-Dioxides. Tetrahedron 1995, 51, 3221-3234.
Lejeune, R.; Delarge, J.; Thunus, L. Préparation du Mercapto-3 pyridinesulfonamide-2. J. Pharm. Belg. 1984, 39, 217-224.
Chomczynski, P.; Sacchi, N. Single-step Method of RNA Isolation by Acid Guanidinium Thiocyanate-phenol-chloroform Extraction. Anal. Biochem. 1987, 162, 156-159.
Wallace, R. A.; Jared, D. W.; Dumont, J. M.; Sega, M. W. Protein Incorporation by Isolated Amphibian Oocytes. III. Optimum Incubation Conditions. J. Exp. Zool. 1973, 184, 321-334.
Randle, J. C. R.; Guet, T.; Bobichon, C.; Moreau, C.; Curutchet, P.; Lambolez, B.; Prado de Carvalho, L.; Cordi, A.; Lepagnol, J. M. Quinoxaline Derivatives: Structure-activity Relationship and Physiological Implications of Inhibition of NMDA and Non-NMDA Receptor-mediated Currents ans Synaptic Potentials. Mol. Pharmacol. 1992, 41, 337-345.