AMPA receptor agonists: Synthesis, protolytic properties, and pharmacology of 3-isothiazolol bioisosteres of glutamic acid

Journal of Medicinal Chemistry

Volumn 40, Issue 4, 1997, Pages 520-527

  Matzen, Lisa ^a   Engesgaard, Anne ^a   Ebert, Bjarke ^a   Didriksen, Michael ^b   Frølund, Bente ^a   Krogsgaard Larsen, Povl ^a   Jaroszewski, Jerzy W ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b H LUNDBECK A S   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 3 (3 HYDROXY 5 METHYLISOTHIAZOL 4 YL)PROPIONIC ACID; ALPHA AMINO 3 HYDROXY 5 METHYL 4 ISOXAZOLEPROPIONIC ACID; AMPA RECEPTOR; AMPA RECEPTOR AGONIST; GLUTAMIC ACID; N METHYL DEXTRO ASPARTIC ACID; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ARTICLE; BLOOD BRAIN BARRIER; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROPHYSIOLOGY; NEUROTRANSMISSION;

ALPHA-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID; ANIMALS; ANTICONVULSANTS; GLUTAMIC ACID; MICE; N-METHYLASPARTATE; RATS; RECEPTORS, AMPA; RECEPTORS, KAINIC ACID; THIAZOLES;

EID: 0031042678     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9607212     Document Type: Article

References (50)

1. Krogsgaard-Larsen, P., Hansen, J. J., Eds. Excitatory Amino Acid Receptors. Design of Agonists and Antagonists; Ellis Horwood: Chichester, 1992.
2. Collingridge, G. L., Watkins, J. C., Eds. The NMDA Receptor; Oxford University Press: Oxford, 1994.
3. Wheal, H. V., Thomson, A. M., Eds. Excitatory Amino Acids and Synaptic Transmission; Academic Press: London, 1995.
4. Conn, P. J., Patel, J., Eds. The Metabotropic Glutamate Receptors; Humana Press: New Jersey, 1994.
5. Danysz, W.; Parsons, C. G.; Bresink, I.; Quack, G. Glutamate in CNS disorders. Drug News Perspect. 1995, 8, 261-277.
6. Knöpfel, T.; Kuhn, R.; Allgeier, H. Metabotropic glutamate receptors: Novel targets for drug development. J. Med. Chem. 1995, 38, 1417-1426.
7. Deutsch, S. I.; Morihisa, J. M. Glutamatergic abnormalities in Alzheimer's disease and a rationale for clinical trials with L-glutamate. Clin. Neuropharmacol. 1988, 11, 18-35.
8. Greenamyre, J. T.; Young, A. B. Excitatory amino acids and Alzheimer's disease. Neurobiol. Aging 1989, 10, 593-602.
9. Bowen, D. M. Treatment of Alzheimer's disease. Molecular pathology versus neurotransmitter-based therapy. Br. J. Psychiat. 1990, 157, 327-330.
10. Madsen, U.; Ebert, B.; Krogsgaard-Larsen, P. Modulation of AMPA receptor function in relation to glutamatergic abnormalities in Alzheimer's disease. Biomed. Pharmacother. 1994, 48, 305-311.
11. Carlsson, M.; Carlsson, A. Interactions between glutamatergic and monoaminergic systems within the basal ganglia - implications for schizophrenia and Parkinson's disease. Trends Neurosci. 1990, 13, 272-276.
12. Ulas, J.; Cotman, C. W. Excitatory amino acid receptors in schizophrenia. Schizophrenia Bull. 1993, 19, 105-117.
13. 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.
14. Ebert, B.; Søby, K. K.; Madsen, U.; Krogsgaard-Larsen, P. Glutamic acid receptors in schizophrenia and Alzheimer's disease: Functional partial agonism and receptor modulation as potential therapeutic approaches. In Schizophrenia - An Integrated View; Fog, R., Gerlach, J., Hemmingsen, R., Eds.; Munksgaard: Copenhagen, 1995; pp 379-395.
15. 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 agonists, partial agonists and antagonists: ibotenic acid as a key lead structure. Eur. J. Med. Chem. 1996, 31, 515-537.
16. Ebert, B.; Madsen, U.; Lund, T. M.; Lenz, S. M.; Krogsgaard-Larsen, P. Molecular pharmacology of the AMPA agonist, (S)-2-amino-3-(3-hydroxy-5-phenyl-4-isoxazolyl)-propionic acid [(S)-APPA] and the AMPA antagonist, (R)-APPA. Neurochem. Int. 1994, 24, 507-515.
17. Ebert, B.; Lenz, S. M.; Brehm, L.; Bregnedal, P.; Hansen, J. J.; Frederiksen, K.; Bøgesø, K. P.; Krogsgaard-Larsen, P. Resolution, absolute stereochemistry, and pharmacology of the S-(+)- and R-(-)-isomers of the apparent partial AMPA receptor agonist (R,S)-2-ammo-3-(3-hydroxy-5-phenylisoxazol-4-yl)propionic acid [(R,S)-APPA]. J. Med. Chem. 1994, 37, 878-884.
18. Ebert, B.; Madsen, U.; Søby, K. K.; Krogsgaard-Larsen, P. Functional partial agonism at ionotropic excitatory amino acid receptors. Neurochem. Int. 1996, 29, 309-316.
19. Lauridsen, J.,' Honoré, T.; Krogsgaard-Larsen, P. Ibotenic acid analogues. Synthesis, molecular flexibility, and in vitro activity of agonists and antagonists at central glutamic acid receptors. J. Med. Chem. 1985, 28, 668-672.
20. Krogsgaard-Larsen, P.; Brehm, L.; Johansen, J. S.; Vinzents, P.; Lauridsen, J.; Curtis, D. R. Synthesis and structure-activity studies on excitatory amino acids structurally related to ibotenic acid. J. Med. Chem. 1985, 28, 673-679.
21. Ebert, B.; Madsen, U.; Lund, T. M.; Holm, T.; Krogsgaard-Larsen, P. Molecular pharmacology of cortical and spinal AMPA receptors. Mol. Neuropharmacol. 1992, 2, 47-49.
22. Madsen, U.; Frølund, B.; Lund, T. M.; Ebert, B.; Krogsgaard-Larsen, P. Design, synthesis and pharmacology of model compounds for indirect elucidation of the topography of AMPA B receptor sites. Eur. J. Med. Chem. 1993, 28, 791-800.
23. Christensen, I. T.; Ebert, B.; Madsen, U.; Nielsen, B.; Brehm, L.; Krogsgaard-Larsen, P. Excitatory amino acid receptor ligands. Synthesis and biological activity of 3-isoxazolol amino acids structurally related to homoibotenic acid. J. Med. Chem. 1992, 35, 3512-3519.
24. Skjærbæk, N.; Ebert, B.; Falch, E.; Brehm, L.; Krogsgaard-Larsen, P. Excitatory amino acids. Synthesis of (RS)-2-amino-3-(5-cyclopropyl-3-hydroxyisoxazol-4-yl)propionic acid, a new potent and specific AMPA receptor agonist. J. Chem. Soc., Perkin Trans. I 1995, 221-225.
25. Sløk, F. A.; Ebert, B.; Lang, Y.; Krogsgaard-Larsen, P.; Lenz, S. M.; Madsen, U. Excitatory amino acid receptor agonists. Synthesis and pharmacology of analogues of 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA). Eur. J. Med. Chem. 1996, in press.
26. Turski, L.; Jacobsen, P.; Honoré, T.; Stephens, D. N. Relief of experimental spasticity and anxiolytic/anticonvulsant actions of the α-amino-3-hydroxy-5-methyl-4-isoxazolepropionate antagonist 2,3-dihydroxy-6-nitro-7-sulfamoylbenzo(F)quinoxaline. J. Pharmacol. Exp. Ther. 1992, 260, 742-747.
27. Arnt, J.; Sánchez, C.; Lenz, S. M.; Madsen, U.; Krogsgaard-Larsen, P. Differentiation of in vivo effects of AMPA and NMDA receptor ligands using drug discrimination methods and convulsant anticonvulsant activity. Eur. J. Pharmacol. 1995, 285, 289-297.
28. Krogsgaard-Larsen, P. γ-Aminobutyric acid agonists, antagonists, and uptake inhibitors. Design and therapeutic aspects. J. Med. Chem. 1981, 24, 1377-1383.
29. Krogsgaard-Larsen, P.; Mikkelsen, H.; Jacobsen, P.; Falch, E.; Curtis, D. R.; Peet, M. J.; Lean, J. D. 4,5,6,7-Tetrahydroisothiazolo[5,4-c]pyridin-3-ol and related analogues of THIP. Synthesis and biological activity. J. Med. Chem. 1983, 26, 895-900.
30. A receptor agonists, partial agonists and antagonists. Design and therapeutic prospects. J. Med. Chem. 1994, 37, 2489-2505.
31. Krogsgaard-Larsen, P.; Hjeds, H.; Curtis, D. R.; Lodge, D.; Johnston, G. A. R. Dihydromuscimol, thiomuscimol and related heterocyclic compounds as GABA analogues. J. Neurochem. 1979, 32, 1717-1724.
32. Hansen, J. J.; Krogsgaard-Larsen, P. Isoxazole amino-acids as glutamic acid agonists. Synthesis of some analogs and homologs of ibotenic acid. J. Chem. Soc., Perkin Trans. 1 1980, 1826-1833.
33. Krogsgaard-Larsen, P.; Honore, T.; Hansen, J. J.; Curtis, D. R.; Lodge, D. New class of glutamate agonist structurally related to ibotenic acid. Nature (London) 1980, 284, 64-66.
34. Krogsgaard-Larsen, P.; Hansen, J. J.; Lauridsen, J.; Peet, M. J.; Leah, J. D.; Curtis, D. R. Glutamic acid agonists, stereo-chemical and conformational studies of DL-α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) and related compounds. Neurosci. Lett. 1982, 37, 313-317.
35. Hansen, J. J.; Nielsen, B.; Krogsgaard-Larsen, P.; Brehm, L.; Nielsen, E. O.; Curtis, D. R. Excitatory amino acid agonists. Enzymic resolution, X-ray structure and enantioselective activities of (R)- and (S)-bromohomoibotenic acid. J. Med. Chem. 1989, 32, 2252-2260.
36. Bischoff, F.; Johansen, T. N.; Ebert, B.; Krogsgaard-Larsen, P.; Madsen, U. Excitatory amino acid receptor ligands: Asymmetric synthesis, absolute stereochemistry and pharmacology of (R)- and (S)-homoibotenic acid. Bioorg. Med. Chem. 1995, 3, 553-558.
37. Goerdeler, J.; Mittler, W. Synthese von 3-Hydroxy-, 3-Alkoxy-und 3-Amino-isothiazolen. (Synthesis of 3-Hydroxy-, 3-Alkoxy- and 3-Amino-isothiazoles.) Chem. Ber. 1963, 96, 944-954.
38. Begtrup, M.; Sløk, F. A. Equilibrium control in bromomethylation: an expedient route to 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA). Synthesis 1993, 861-863.
39. Lykkeberg, J.; Krogsgaard-Larsen, P. Structural analogues of GABA. Synthesis of 5-aminomethyl-3-isothiazolol (Thiomuscimol). Acta Chem. Scand. 1976, B30, 781-785.
40. Soai, K.; Oyamada, H. A chemoselective one-step reduction of β-ketoesters to 1,3-diols. Synthesis 1984, 605-607.
41. Freedman, M. H.; Lyerla, J. R.; Chaiken, I. N.; Cohen, J. S. Carbon-13 nuclear magnetic resonance studies on selected amino acids, peptides, and proteins. Eur. J. Biochem. 1973, 32, 215-226.
42. Frydenvang, K.; Matzen, L.; Jaroszewski, J. W.; Norrby, P.-O.; Liljefors, T.; Krogsgaard-Larsen, P. Structural characteristics of the moieties of 3-isoxazolol and 3-isothiazolol. J. Chem. Soc., Perkin Trans. II 1996, submitted.
43. Quirt, A. R.; Lyerla, J. R.; Peat, I. R.; Cohen, J. S.; Reynolds, W. F.; Freedman, M. H. Carbon-13 nuclear magnetic resonance titration shifts in amino acids. J. Am. Chem. Soc. 1974, 23, 570-574.
44. Honoré, T.; Nielsen, M. Complex structure of quiqualate-sensitive glutamate receptors in rat cortex. Neurosci. Lett. 1985, 54, 27-32.
45. 3H]3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid to rat membranes. A selective high affinity ligand for N-methyl-D-aspartate receptors. J. Pharmacol. Exp. Ther. 1987, 240, 778-783.
46. 3H]kainic acid receptor binding by divalent cations correlates with ion affinity for the calcium channel. Neuropharmacology 1987, 26, 1247-1251.
47. Sheardown, M. J.; Nielsen, E. Ø.; Hansen, A. J.; Jacobsen, P.; Honoré, T. 2,3-Dihydroxy-6-nitro-7-sulfamoyl-benzo(F)quinoxaline. A neuroprotectant for cerebral ischemia. Science 1990, 247, 571-574.
48. Swamer, F. W.; Hauser, C. R. Claisen acylations and carbethoxylations of ketones and esters by means of sodium hydride. J. Am. Chem. Soc. 1950, 72, 1352-1356.
49. 3H]MK-801 to the N-methyl-D-aspartate receptor ion channel complex by L-glutamate, glycine and polyamines. J. Neurochem. 1988, 51, 830-836.
50. Harrison, N. L.; Simmonds, M. A. Quantitative studies on some antagonists of N-methyl-D-aspartate in slices of rat cerebral cortex. Br. J. Pharmacol. 1985, 84, 381-391.