Resolution, configurational assignment, and enantiopharmacology at glutamate receptors of 2-amino-3-(3-carboxy-5-methyl-4-isoxazolyl)propionic acid (ACPA) and demethyl-ACPA

Chirality

Volumn 13, Issue 9, 2001, Pages 523-532

  Johansen, Tommy N ^a   Stensbøl, Tine B ^a   Nielsen, Birgitte ^a   Vogensen, Stine B ^a   Frydenvang, Karla ^a   Sløk, Frank A ^a   Bräuner Osborne, Hans ^a   Madsen, Ulf ^a   Krogsgaard Larsen, Povl ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

AMPA receptor agonism; Chiral HPLC; Metabotropic receptor antagonism; X ray crystallography

Indexed keywords

2 AMINO 3 (3 CARBOXY 4 ISOXAZOLYL)PROPIONIC ACID; 2 AMINO 3 (3 CARBOXY 5 METHYL 4 ISOXAZOLYL)PROPIONIC ACID; AMPA RECEPTOR; AMPA RECEPTOR AGONIST; GLUTAMATE RECEPTOR; KAINIC ACID; KAINIC ACID RECEPTOR; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; PROPIONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; ASSAY; BINDING AFFINITY; BRAIN CORTEX; BRAIN ELECTROPHYSIOLOGY; BRAIN SLICE; CHIRAL CHROMATOGRAPHY; CHO CELL; CHROMATOGRAPHY; CIRCULAR DICHROISM; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG RECEPTOR BINDING; DRUG STRUCTURE; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IC 50; IN VITRO STUDY; NONHUMAN; PRIORITY JOURNAL; RAT; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

ALANINE; ANIMALS; CHO CELLS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CLONING, MOLECULAR; CRICETINAE; CRYSTALLOGRAPHY, X-RAY; ELECTROPHYSIOLOGY; EXCITATORY AMINO ACID AGONISTS; INDICATORS AND REAGENTS; ISOXAZOLES; MODELS, MOLECULAR; PROTEIN CONFORMATION; RATS; RECEPTORS, GLUTAMATE; SECOND MESSENGER SYSTEMS; STEREOISOMERISM;

EID: 0034778767     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.1172     Document Type: Article

References (13)

1. Bräuner-Osborne H, Egebjerg J, Nielsen EØ, Madsen U, Krogsgaard-Larsen P. Ligands for glutamate receptors: design and therapeutic prospects. J Med Chem 2000;43:2609-2645.
2. Bleakman D, Lodge D. Neuropharmacology of AMPA and kainate receptors. Neuropharmacology 1998;37:1187-1204.
3. Knöpfel T, Kühn R, Allgeier H. Metabotropic glutamate receptors: novel targets for drug development. J Med Chem 1995;38:1417-1426.
4. Conn PJ, Pin J-P. Pharmacology and functions of metabotropic glutamate receptors. Annu Rev Pharmacol Toxicol 1997;37:205-237.
5. Schoepp DD, Jane DE, Monn JA. Pharmacological agents acting at subtypes of metabotropic glutamate receptors. Neuropharmacology 1999;38:1431-1476.
6. Sløk FA, Ebert B, Lang Y, Krogsgaard-Larsen P, Lenz SM, 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.
7. Bang-Andersen B, Lenz SM, Skjærbæk N, Soby KK, Hansen HO, Ebert B, Bogesø KP, Krogsgaard-Larsen P. Heteroaryl analogues of AMPA. Synthesis and quantitative structure-activity relationships. J Med Chem 1997;40:2831-2842.
8. Falch E, Brehm L, Mikkelsen I, Johansen TN, Skjærbæk N, Nielsen B, Stensbol TB, Ebert B, Krogsgaard-Larsen P. Heteroaryl analogues of AMPA. 2. Synthesis, absolute stereochemistry, photochemistry, and structure-activity relationships. J Med Chem 1998;41:2513-2523.
9. Madsen U, Wong EHF. Heterocyclic excitatory amino acids. Synthesis and biological activity of novel analogues of AMPA. J Med Chem 1992;35:107-111.
10. Wahl P, Madsen U, Banke T, Krogsgaard-Larsen P, Schousboe A. Different characteristics of AMPA receptor agonists acting at AMPA receptors expressed in Xenopus oocytes. Eur J Pharmacol 1996;308:211-218.
11. 3H]2-amino-3-(3-carboxy-5-methyl-4-isoxazolyl)propionic acid. Eur J Pharmacol 1999;373:251-262.
12. 2-isoxazolin-5-ols and their acetates. Can J Chem 1970;48:467-476.
13. Enraf-Nonius. CAD-4 Software; v. 5.0. Delft, The Netherlands: Enraf-Nonius; 1989.