Heteroaryl analogues of AMPA. Synthesis and quantitative structure- activity relationships

Journal of Medicinal Chemistry

Volumn 40, Issue 18, 1997, Pages 2831-2842

  Bang Andersen, Benny ^a   Lenz, Sibylle M ^a   Skjærbæk, Niels ^b   Søby, Karina K ^a   Hansen, Hans O ^a   Ebert, Bjarke ^b   Bøgesø, Klaus P ^a   Krogsgaard Larsen, Povl ^b  

^a H LUNDBECK A S   (Denmark)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 4 PHOSPHONOMETHYL 3 HEPTENOIC ACID; ALPHA AMINO 3 HYDROXY 5 METHYL 4 ISOXAZOLEPROPIONIC ACID; AMINO ACID RECEPTOR STIMULATING AGENT; AMPA RECEPTOR; EXCITATORY AMINO ACID; GLUTAMATE RECEPTOR; HETEROCYCLIC COMPOUND; KAINIC ACID; N METHYL DEXTRO ASPARTIC ACID; N METHYL DEXTRO ASPARTIC ACID RECEPTOR;

ANIMAL TISSUE; ARTICLE; BRAIN CORTEX; BRAIN SLICE; CONTROLLED STUDY; DRUG CONFORMATION; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; HYDROGEN BOND; LIGAND BINDING; LIPOPHILICITY; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT; RECEPTOR AFFINITY;

ALPHA-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID; ANIMALS; BINDING, COMPETITIVE; CEREBRAL CORTEX; CORPUS CALLOSUM; ELECTROPHYSIOLOGY; EVOKED POTENTIALS; ISOXAZOLES; KAINIC ACID; KINETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; POTENTIOMETRY; RATS; RECEPTORS, AMPA; RECEPTORS, KAINIC ACID; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030820888     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970253b     Document Type: Article

References (46)

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 Synoptic Transmission; Academic Press: London, 1995.
4. Monaghan, D. T., Wenthold, R. J., Eds. The Ionotropic Glutamate Receptors; Humana Press: New Jersey, 1997.
5. Conn, P. J., Patel, J., Eds. The Metabotropic Glutamate Receptors; Humana Press: New Jersey, 1994.
6. Danysz, W.; Parsons, C. G.; Bresink, I.; Quack, G. Glutamate in CNS disorders. Drug News Perspect. 1995, 8, 261-277.
7. Knöpfel, T.; Kuhn, R.; Allgeier, H. Metabotropic glutamate receptors: Novel targets for drug development. J. Med. Chem. 1995, 38, 1417-1426.
8. 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.
9. Greenamyre, J. T.; Young, A. B. Excitatory amino acids and Alzheimer's disease. Neurobiol. Ag. 1989, 10, 593-602.
10. Bowen, D. M. Treatment of Alzheimer's disease. Molecular pathology versus neurotransmitter-based therapy. Br. J. Psychiat. 1990, 157, 327-330.
11. 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.
12. 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.
13. Ulas, J.; Cotman, C. W. Excitatory amino acid receptors in schizophrenia. Schizophrenia Bull. 1993, 19, 105-117.
14. 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.
15. 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 379-398.
16. Hansen, J. J.; Krogsgaard-Larsen, P. Structural, conformational, and stereochemical requirements of central excitatory amino acid receptors. Med. Res. Rev. 1990, 10, 55-94.
17. 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.
18. 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.
19. Krogsgaard-Larsen, P.; Hansen, J. J.; Lauridsen, J.; Peet, M. J.; Leah, J. D.; Curtis, D. R. Glutamic acid agonists, stereochemical and conformational studies of DL-α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) and related compounds. Neurosci. Lett. 1982, 31, 313-317.
20. 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. Eur. J. Med. Chem. 1997, 32, 329-338.
21. 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.
22. Johansen, T. N.; Frydenvang, K.; Ebert, B.; Krogsgaard-Larsen, P.; Madsen, U. Synthesis and structure-activity studies on acidic amino acids and related diacids as NMDA receptor ligands. J. Med. Chem. 1994, 37, 3252-3262.
23. 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-amino-3-(3-hydroxy-5-phenylisoxazol-4-yl)propionic acid [(R,S)APPA]. J. Med. Chem. 1994, 37, 878-884.
24. 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.
25. Moltzen, S. L.; Falch, E.; Bøgesø, K. P.; Krogsgaard-Larsen, P. 5-Arylisoxazolyl-4-yl-substituted 2-amino carboxylic acid compounds. PCT Int. Appl. No. 9512, 587; Chem. Abstr. 1995, 123, 112056n.
26. 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.
27. Madsen, U.; Nielsen, E. Ø.; Curtis, D. R.; Beattie, D. T.; Krogsgaard-Larsen, P. Synthesis and single cell pharmacology of potential heterocyclic bioisosteres of the excitatory amino acid antagonist glutamic acid diethyl ester. Acta Chem. Scand. 1990, 44, 96-102.
28. Newman, M. S.; Arkell, A.; Fukunaga, T. The synthesis and some reactions of di-t-butylacetic acid and di-f-butylketene. J. Am. Chem. Soc. 1960, 82, 2498-2501.
29. Finnegan, W. G.; Henry, R. A.; Lofquist, R. An improved synthesis of 5-substituted tetrazoles. J. Am. Chem. Soc. 1958, 80, 3908-3911.
30. Reese, C. B.; Zhang, P. Z. Phosphotriester approach to the synthesis of oligonucleotides: A reappraisal. J. Chem. Soc., Perkin Trans. 1 1993, 2291-2301.
31. Kadaba, P. K. Protic-dipolar aprotic solvents in 1,3-cycloaddition reactions. Role of dipolar aprotic solvents in cycloadditions involving anionic 1,3-dipoles and an improved synthesis of 1,5-substituted tetrazoles. Synth. Commun. 1971, 1, 1-5.
32. Lin, Y. I.; Lang, S. A., Jr.; Lovell, M. F.; Perkinson, N. A. New synthesis of 1,2,4-triazoles and 1,2,4-oxadiazoles. J. Org. Chem. 1979, 44, 4160-4164.
33. Atkinson, M. R.; Polya, J. B. Triazoles. Part III. Mono- and dimethyl(phenyl)-1,2,4-triazoles. J. Chem. Soc., Perkin Trans. 1 1954, 3319-3324.
34. Case, F. H. The preparation of hydrazidines and as-triazines related to substituted 2-cyanopyridines. J. Org. Chem. 1965, 30, 931-933.
35. 3H]CGP 39653: A new N-methyl-D-aspartate antagonist radioligand with low nanomolar affinity in rat brain. Eur. J. Pharmacol. 1991, 192, 19-24.
36. Honoré, T.; Nielsen, M. Complex structure of quisqualate-sensitive glutamate receptors in rat cortex. Neurosci. Lett. 1985, 54, 27-32.
37. 3H]kainic acid receptor binding by divalent cations correlates with ion affinity for the calcium channel. Neuropharmacology 1987, 26, 1247-1251.
38. 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.
39. Brehm, L.; Jørgensen, F. S.; Hansen, J. J.; Krogsgaard-Larsen, P. Agonists and antagonists for central glutamic acid receptors. Drug News Perspect. 1988, 1, 138-144.
40. 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 receptor sites. Eur. J. Med. Chem. 1993, 28, 791-800.
41. Madsen, U.; Ebert, B.; Krogsgaard-Larsen, P.; Wong, E. H. F. Synthesis and pharmacology of (RS)-2-amino-3-(3-hydroxy-5-trifluoromethyl-4-isoxazolyl)propionic acid, a potent AMPA receptor agonist. Eur. J. Med. Chem. 1992, 27, 479-484.
42. Parham, W. E.; Wynberg, H.; Ramp, F. L. Heterocyclic Vinyl Ethers. III. The Synthesis of 1,4-Dithiadiene and 1,4-Dithiadiene Disulfone. J. Am. Chem. Soc. 1953, 75, 2065-2069.
43. 3H]MK-801 Binding to the N-Methyl-D-aspartate Receptor-Ion Channel Complex by L-Glutamate, Glycine, and Polyamines. J. Neurochem. 1988, 51, 830-836.
44. Clarke, F. H.; Gaboon, N. M. Ionization constants by curve fitting: Determination of partition and distribution coefficients of acids and bases and their ions. J. Pham. Sci. 1987, 76, 611-620.
45. MacMimic, 2.0. The program MacMimic and a Macintosh version of the MM2(91) program is available from InStar Software AB, Ideon Research Park, S-223 70 Lund, Sweden.
46. SPARTAN Wavefunction, Inc., 18401 Von Karman Ave., Suite 370, Irvine, CA 92715.