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Volumn 9, Issue 5-6, 1997, Pages 529-536

Excitatory amino acid receptor antagonists: Resolution, absolute stereochemistry, and pharmacology of (S)- and (R)-2 -amino-2-(5- tert-butyl- 3-hydroxyisoxazol-4-yl) acetic acid (ATAA)

Author keywords

Absolute stereochemistry; AMPA receptor antagonist; Chiral HPLC; Diastereomeric salt resolution; Enantiomeric purity; NMDA receptor antagonist; X ray crystallography

Indexed keywords

2 AMINO 2 (5 TERT BUTYL 3 HYDROXYISOXAZOL 4 YL)ACETIC ACID; 4 (3 PHOSPHONOPROPYL) 2 PIPERAZINECARBOXYLIC ACID; AMPA RECEPTOR ANTAGONIST; EXCITATORY AMINO ACID RECEPTOR; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG;

EID: 0030955204     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1997)9:5/6<529::AID-CHIR20>3.0.CO;2-P     Document Type: Article
Times cited : (10)

References (36)
  • 6
    • 0020549223 scopus 로고
    • Enzymic resolution and binding to rat brain membranes of the glutamic acid agonist, α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
    • Hansen, J.J., Lauridsen, J., Nielsen, E., Krogsgaard-Larsen, P. Enzymic resolution and binding to rat brain membranes of the glutamic acid agonist, α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid. J. Med. Chem. 26:901-903, 1983.
    • (1983) J. Med. Chem. , vol.26 , pp. 901-903
    • Hansen, J.J.1    Lauridsen, J.2    Nielsen, E.3    Krogsgaard-Larsen, P.4
  • 7
    • 0021910630 scopus 로고
    • Ibotenic acid analogues. Synthesis, molecular flexibility, and in vitro activity of agonists and antagonists at central glutamic acid receptors
    • 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. 28:668-672, 1985.
    • (1985) J. Med. Chem. , vol.28 , pp. 668-672
    • Lauridsen, J.1    Honoré, T.2    Krogsgaard-Larsen, P.3
  • 8
    • 0020287345 scopus 로고
    • Glutamic acid agonists, stereochemical and conformational studies of DL-α-amino-3-hydroxy-5-methyl-4-isoxazole-propionic acid (AMPA) and related compounds
    • 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-isoxazole-propionic acid (AMPA) and related compounds. Neurosci. Lett. 31: 313-317, 1982.
    • (1982) Neurosci. Lett. , vol.31 , pp. 313-317
    • Krogsgaard-Larsen, P.1    Hansen, J.J.2    Lauridsen, J.3    Peet, M.J.4    Leah, J.D.5    Curtis, D.R.6
  • 9
    • 0025117827 scopus 로고
    • 2,3-Dihydroxy-6-nitro-7-sulfamoyl-benzo(F)quinoxaline. A neuroprotectant for cerebral ischemia
    • 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 247:571-574, 1990.
    • (1990) Science , vol.247 , pp. 571-574
    • Sheardown, M.J.1    Nielsen, E.Ø.2    Hansen, A.J.3    Jacobsen, P.4    Honoré, T.5
  • 10
    • 0028202566 scopus 로고
    • 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]
    • 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. 37:878-884, 1994.
    • (1994) J. Med. Chem. , vol.37 , pp. 878-884
    • Ebert, B.1    Lenz, S.M.2    Brehm, L.3    Bregnedal, P.4    Hansen, J.J.5    Frederiksen, K.6    Bøgesø, K.P.7    Krogsgaard-Larsen, P.8
  • 11
    • 0028272399 scopus 로고
    • 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
    • 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. 24:507-515, 1994.
    • (1994) Neurochem. Int. , vol.24 , pp. 507-515
    • Ebert, B.1    Madsen, U.2    Lund, T.M.3    Lenz, S.M.4    Krogsgaard-Larsen, P.5
  • 14
    • 0028928489 scopus 로고
    • Metabotropic glutamate receptors: Novel targets for drug development
    • Knöpfel, T., Kuhn, R., Allgeier, H. Metabotropic glutamate receptors: Novel targets for drug development. J. Med. Chem. 38:1417-1426, 1995.
    • (1995) J. Med. Chem. , vol.38 , pp. 1417-1426
    • Knöpfel, T.1    Kuhn, R.2    Allgeier, H.3
  • 16
    • 0030024147 scopus 로고    scopus 로고
    • N-Methyl-D-aspartic acid receptor agonists. Resolution, absolute stereochemistry and pharmacology of the enantiomers of 2-amino-2-(3-hydroxy-5-methyl-4-isoxazolyl) acetic acid (AMAA)
    • Madsen, U., Frydenvang, K., Ebert, B., Johansen, T.N., Brehm, L., Krogsgaard-Larsen, P. N-Methyl-D-aspartic acid receptor agonists. Resolution, absolute stereochemistry and pharmacology of the enantiomers of 2-amino-2-(3-hydroxy-5-methyl-4-isoxazolyl) acetic acid (AMAA). J. Med. Chem. 39:183-190, 1996.
    • (1996) J. Med. Chem. , vol.39 , pp. 183-190
    • Madsen, U.1    Frydenvang, K.2    Ebert, B.3    Johansen, T.N.4    Brehm, L.5    Krogsgaard-Larsen, P.6
  • 17
    • 0028062168 scopus 로고
    • Synthesis and structure-activity studies on acidic amino acids and related diacids as NMDA receptor ligands
    • 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. 37:3252-3262, 1994.
    • (1994) J. Med. Chem. , vol.37 , pp. 3252-3262
    • Johansen, T.N.1    Frydenvang, K.2    Ebert, B.3    Krogsgaard-Larsen, P.4    Madsen, U.5
  • 18
    • 0026563864 scopus 로고
    • Relief of experimental spasticity and anxiolytic/anticonvulsant actions of the α-amino-3-hydroxy-5-methyl-4-isoxazole-propionate antagonist 2,3-dihydroxy-6-nitro-7-sulfamoylbenzo(F)quinoxaline
    • 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-isoxazole-propionate antagonist 2,3-dihydroxy-6-nitro-7-sulfamoylbenzo(F)quinoxaline. J. Pharmacol. Exp. Ther. 260: 742-747, 1992.
    • (1992) J. Pharmacol. Exp. Ther. , vol.260 , pp. 742-747
    • Turski, L.1    Jacobsen, P.2    Honoré, T.3    Stephens, D.N.4
  • 19
    • 0000370860 scopus 로고
    • Resolution of the optical isomers of underivatisized amino acids on chemically bound chiral phases by ligand exchange chromatography
    • Gübitz, G., Jellenz, W., Santi, W. Resolution of the optical isomers of underivatisized amino acids on chemically bound chiral phases by ligand exchange chromatography. J. Liq. Chromatogr. 4:701-712, 1981.
    • (1981) J. Liq. Chromatogr. , vol.4 , pp. 701-712
    • Gübitz, G.1    Jellenz, W.2    Santi, W.3
  • 20
    • 0001431519 scopus 로고
    • DREADD: Data reduction and error analysis for single-crystal diffractometer data
    • Blessing, R.H. DREADD: data reduction and error analysis for single-crystal diffractometer data. J. Appl. Cryst. 22:396-397, 1989.
    • (1989) J. Appl. Cryst. , vol.22 , pp. 396-397
    • Blessing, R.H.1
  • 21
    • 84943920736 scopus 로고
    • Phase annealing in SHELX-90: Direct methods for larger structures
    • Sheldrick, G.M. Phase annealing in SHELX-90: Direct methods for larger structures. Acta Crystallogr. A46:467-473, 1990.
    • (1990) Acta Crystallogr. , vol.A46 , pp. 467-473
    • Sheldrick, G.M.1
  • 23
    • 84944438568 scopus 로고
    • On enantiomorph-polarity estimation
    • Flack, H.D. On enantiomorph-polarity estimation. Acta Crystallogr. A39:876-881, 1983.
    • (1983) Acta Crystallogr. , vol.A39 , pp. 876-881
    • Flack, H.D.1
  • 24
    • 0022005967 scopus 로고
    • Quantitative studies on some antagonists of N-methyl-D-aspartate in slices of rat cerebral cortex
    • 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. 84:381-391, 1985.
    • (1985) Br. J. Pharmacol. , vol.84 , pp. 381-391
    • Harrison, N.L.1    Simmonds, M.A.2
  • 25
    • 0010426145 scopus 로고
    • A simple method for recording excitatory amino acid-evoked depolarizations of rat cortex in vitro
    • Wheatley, P.L. A simple method for recording excitatory amino acid-evoked depolarizations of rat cortex in vitro. Br. J. Pharmacol. 87:159, 1986.
    • (1986) Br. J. Pharmacol. , vol.87 , pp. 159
    • Wheatley, P.L.1
  • 26
    • 0023658988 scopus 로고
    • Chromatographic separation of racemic amino acids by use of chiral crown ether-coated reversed-phase packings
    • Shinbo, T., Yamagushi, T., Nishimura, K., Sugiura, M. Chromatographic separation of racemic amino acids by use of chiral crown ether-coated reversed-phase packings. J. Chromatogr. 405:145-153, 1987.
    • (1987) J. Chromatogr. , vol.405 , pp. 145-153
    • Shinbo, T.1    Yamagushi, T.2    Nishimura, K.3    Sugiura, M.4
  • 27
    • 0003653439 scopus 로고
    • Oak Ridge, TN: Oak Ridge National Laboratory
    • Johnson, C.K. ORTEPII Report ORNL-5138. Oak Ridge, TN: Oak Ridge National Laboratory, 1976.
    • (1976) ORTEPII Report ORNL-5138
    • Johnson, C.K.1
  • 28
    • 84982075208 scopus 로고
    • Spectropolarimetry II: The optical rotatory dispersion of α-amino-acids and α-hydroxy-acids
    • Dirkx, I.P., Sixma, F.L.J. Spectropolarimetry II: The optical rotatory dispersion of α-amino-acids and α-hydroxy-acids. Reel. Trav. Chim. Pay-Bas 83:522-534, 1964.
    • (1964) Reel. Trav. Chim. Pay-Bas , vol.83 , pp. 522-534
    • Dirkx, I.P.1    Sixma, F.L.J.2
  • 29
    • 0343873628 scopus 로고
    • Optical rotatory dispersion. Part X. Amino acids
    • Jennings, J.P., Klyne, W., Scopes, P.M. Optical rotatory dispersion. Part X. Amino acids. J. Chem. Soc. 294-297, 1965.
    • (1965) J. Chem. Soc. , pp. 294-297
    • Jennings, J.P.1    Klyne, W.2    Scopes, P.M.3
  • 31
    • 0030915716 scopus 로고    scopus 로고
    • AMPA receptor agonists: Resolution, configurational assignment and pharmacology of (S)-(+)- and (R)-(-)-2-amino-3-[3-hydroxy-5-(2-pyridyl)isoxazol-4-yl]propionic acid (2-Py-AMPA)
    • in press
    • Johansen, T.N., Ebert, B., Falch, E., Krogsgaard-Larsen, P. AMPA receptor agonists: Resolution, configurational assignment and pharmacology of (S)-(+)-and (R)-(-)-2-amino-3-[3-hydroxy-5-(2-pyridyl)isoxazol-4-yl]propionic acid (2-Py-AMPA). Chirality 1997 in press.
    • Chirality , vol.1997
    • Johansen, T.N.1    Ebert, B.2    Falch, E.3    Krogsgaard-Larsen, P.4
  • 32
    • 0024589206 scopus 로고
    • Excitatory amino acid receptor subtypes and specific antagonists
    • Honoré, T. Excitatory amino acid receptor subtypes and specific antagonists. Med. Res. Rev. 9:1-23, 1989.
    • (1989) Med. Res. Rev. , vol.9 , pp. 1-23
    • Honoré, T.1
  • 33
  • 35
    • 0029819830 scopus 로고    scopus 로고
    • Synthesis of tritiated (RS)-2-amino-2-(3-hydroxy-5-methylisoxazol-4-yl) acetic acid (AMAA), a potent and selective NMDa agonist
    • Johansen, T.N., Balasubramanian, V., Madsen, U., Ferkany, J.W., Krogsgaard-Larsen, P. Synthesis of tritiated (RS)-2-amino-2-(3-hydroxy-5-methylisoxazol-4-yl) acetic acid (AMAA), a potent and selective NMDA agonist. J. Labelled Compd. Radiopharm. 38:915-922, 1996.
    • (1996) J. Labelled Compd. Radiopharm. , vol.38 , pp. 915-922
    • Johansen, T.N.1    Balasubramanian, V.2    Madsen, U.3    Ferkany, J.W.4    Krogsgaard-Larsen, P.5
  • 36
    • 0023160804 scopus 로고
    • Binding sites for A1 excitatory amino acid receptor ligands in crude postsynaptic densities from rat brain
    • Foster, A.C., Fagg, G.E. Binding sites for A1 excitatory amino acid receptor ligands in crude postsynaptic densities from rat brain. Eur. J. Pharmacol. 133:291-300, 1987.
    • (1987) Eur. J. Pharmacol. , vol.133 , pp. 291-300
    • Foster, A.C.1    Fagg, G.E.2


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