Resolution, configurational assignment, and enantiopharmacology of 2-amino-3-[3-hydrpxy-5-(2-methyl-2H-tetrazol-5-yl)isoxazol4-yl]propionic acid, a potent GluR3- and GluR4-preferring AMPA receptor agonist

Chirality

Volumn 12, Issue 10, 2000, Pages 705-713

  Vogensen, Stine B ^a   Jensen, Henrik S ^b   Stensbøl, Tine B ^a   Frydenvang, Karla ^a   Bang Andersen, Benny ^c   Johansen, Tommy N ^a   Egebjerg, Jan ^b   Krogsgaard Larsen, Povl ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b AARHUS UNIVERSITY   (Denmark)

^c H LUNDBECK A S   (Denmark)

Author keywords

AMPA receptor affinity; AMPA receptor agonism; Chiral HPLC; Cloned ionotropic glutamate receptors; Electrophysiology; GluR1 4; Resolution; Subunit selectivity; X ray crystallography

Indexed keywords

2 AMINO 3 [3 HYDROXY 5 (2 METHYL 2H TETRAZOL 5 YL) ISOXAZOL 4 YL]PROPIONIC ACID; AMPA RECEPTOR; AMPA RECEPTOR AGONIST; GLUTAMATE RECEPTOR; GLUTAMATE RECEPTOR AGONIST; ISOXAZOLE DERIVATIVE; KAINIC ACID RECEPTOR; PROPIONIC ACID DERIVATIVE; RECEPTOR SUBTYPE; RECOMBINANT RECEPTOR; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CHIRALITY; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; OOCYTE; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

ANIMAL; CRYSTALLOGRAPHY, X-RAY; EXCITATORY AMINO ACID AGONISTS; FEMALE; ISOXAZOLES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OOCYTES; RADIOLIGAND ASSAY; RECEPTORS, AMPA; RECOMBINANT PROTEINS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SUPPORT, NON-U.S. GOV'T; TETRAZOLES; TRANSCRIPTION, GENETIC; XENOPUS LAEVIS;

EID: 0033783080     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/1520-636X(2000)12:10<705::AID-CHIR2>3.0.CO;2-9     Document Type: Article

References (51)

1. Structure-activity relationships in the development of excitatory amino acid receptor agonists and competitive antagonists
2. A synaptic model of memory: Long-term potentiation in the hippocampus
3. Molecular diversity and functions of glutamate receptors
4. Glutamate in CNS disorders - A revived target for drug development?
5. Metahotropic glutamate receptors: Novel targets for drug development
6. The metabotropic glutamate receptors: Structure and functions
7. The glutamate receptor ion channels
8. Cloned glutamate receptors
9. New developments in the molecular pharmacology of alpha-amino-3-hydroxy-5-methyl-4-isoxazole propionate and kainate receptors
10. Flip and flop: A cell-specific functional switch in glutamate-operated channels of the CNS
11. The role of RNA editing in controlling glutamate receptor channel properties
12. 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)-APPAI
13. 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)
14. Heteroaryl analogues of AMPA Synthesis and quantitative structure-activity relationships
15. Heteroaryl analogues of AMPA. 2. Synthesis, absolute stereochemistry, photochemistry, and structure-activity relationships
16. Resolution of the optical isomers of underivatisized amino acids on chemically bonded chiral phases by ligand exchange chromatography
17. DREADD - Data reduction and error analysis for single-crystal diffractometer data
18. Data reduction and error analysis for accurate single crystal diffraction intensities
19. ABSORB: An absorption correction programme for crystals enclosed in capillaries with trapped mother liquor
20. Phase annealing in SHELX-90: Direct methods for large structures
21. On enanfiomorph-polarity estimation
22. Complex structure of quisqualate-sensitive glutamate receptors in rat cortex
23. 3H]kainic acid receptor binding by divalent cations correlates with ion affinity for the calcium channel
24. 3H]3-(2-carboxypiperazin-4-yl)propyl-l-phosphonic acid to rat membranes. A selective high affinity ligand for N-methyl-D-aspartate receptors
25. Resolution, absolute stereochemistry and molecular pharmacology of the enantiomers of ATPA
26. Quantitative studies on some antagonists of N-methyl-D-aspartate in slices of rat cerebral cortex
27. Design, synthesis and pharmacology of model compounds for indirect elucidation of the topography of AMPA receptor sites
28. Assessing the distribution of parameters in models of ligand-receptor interaction: To log or not to log
29. A covalently bonded teicoplanin chiral stationary phase for HPLC enantioseparations
30. Facile liquid chromatographic enantioresolution of native amino acids and peptides using a teicoplanin chiral stationary phase
31. Structural features of muscimol, a potent GABA(A) receptor agonist. Crystal structure and quantum chemical ab initio calculations
32. Structural characteristics of isoxazol-3-ol and isothiazol-3-ol, carhoxyl group bioisosteres examined by X-ray crystallography and ab initio calculations
33. Tables of bond lengths determined by X-ray and neutron diffraction. 1. Bond lengths in organic compounds
34. Research using the Cambridge Structural Database
35. Chromatographic separation of racemic amino acids by use of chiral crown ether-coated reversed-phase packings
36. Direct separation of enantiomers by high performance ligand exchange chromatography on chemically bonded chiral phases
37. Application of the optical activity to stereochemical determinations
38. Excitatory amino acid receptor ligands: Resolution, absolute stereochemistry, and enantiopharmacology of 2-amino-3-(4-butyl-3-hydroxyisoxazol-5-yl)propionic acid
39. Antagonist properties of a phosphono isoxazole amino acid (ATPO) at GluR1-4 AMPA receptor subtypes
40. A glutamate receptor channel with high affinity for domoate and kainate
41. 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
42. Schizophrenia - An integrated view