Click here to close
Hello! We notice that you are using Internet Explorer, which is not supported by Xenbase and may cause the site to display incorrectly.
We suggest using a current version of Chrome,
FireFox, or Safari.
Neurochem Res
2014 Oct 01;3910:1895-905. doi: 10.1007/s11064-014-1332-0.
Show Gene links
Show Anatomy links
Analogues of 3-hydroxyisoxazole-containing glutamate receptor ligands based on the 3-hydroxypyrazole-moiety: design, synthesis and pharmacological characterization.
Jørgensen L
,
Nielsen B
,
Pickering DS
,
Kristensen AS
,
Frydenvang K
,
Madsen U
,
Clausen RP
.
???displayArticle.abstract???
A series of analogues of the glutamate receptor ligands (S)-2-amino-3-(3-hydroxy-5-methyl-isoxazol-4-yl)propionic acid (AMPA) and AMOA were synthesized in which the 3-hydroxyisoxazole moiety was exchanged for a 3-hydroxypyrazole moiety. This exchange enables further substitution at the additional nitrogen atom in the heterocyclic core. Several of the analogues have activity at AMPA receptors equipotent to the antagonist ATPO, demonstrating that additional substitution can be accommodated in the antagonist binding site. Modelling studies offer an explanation for the pharmacological pattern observed for the compounds and suggest that this scaffold may be developed further to obtain subtype selective antagonists.
Assaf,
Chemoenzymatic synthesis of new 2,4-syn-functionalized (S)-glutamate analogues and structure-activity relationship studies at ionotropic glutamate receptors and excitatory amino acid transporters.
2013, Pubmed
Assaf,
Chemoenzymatic synthesis of new 2,4-syn-functionalized (S)-glutamate analogues and structure-activity relationship studies at ionotropic glutamate receptors and excitatory amino acid transporters.
2013,
Pubmed
Braitman,
Inhibition of [3H]kainic acid receptor binding by divalent cations correlates with ion affinity for the calcium channel.
1987,
Pubmed
Bräuner-Osborne,
Ligands for glutamate receptors: design and therapeutic prospects.
2000,
Pubmed
Hald,
Partial agonism and antagonism of the ionotropic glutamate receptor iGLuR5: structures of the ligand-binding core in complex with domoic acid and 2-amino-3-[5-tert-butyl-3-(phosphonomethoxy)-4-isoxazolyl]propionic acid.
2007,
Pubmed
Hansen,
Structural aspects of AMPA receptor activation, desensitization and deactivation.
2007,
Pubmed
Hermit,
Ibotenic acid and thioibotenic acid: a remarkable difference in activity at group III metabotropic glutamate receptors.
2004,
Pubmed
Hogner,
Competitive antagonism of AMPA receptors by ligands of different classes: crystal structure of ATPO bound to the GluR2 ligand-binding core, in comparison with DNQX.
2003,
Pubmed
Honoré,
Complex structure of quisqualate-sensitive glutamate receptors in rat cortex.
1985,
Pubmed
Javitt,
Glutamate as a therapeutic target in psychiatric disorders.
2004,
Pubmed
Krogsgaard-Larsen,
New class of glutamate agonist structurally related to ibotenic acid.
1980,
Pubmed
Madsen,
Synthesis and pharmacology of highly selective carboxy and phosphono isoxazole amino acid AMPA receptor antagonists.
1996,
Pubmed
Møller,
Resolution, absolute stereochemistry, and enantiopharmacology of the GluR1-4 and GluR5 antagonist 2-amino-3-[5-tert-butyl-3-(phosphonomethoxy)-4-isoxazolyl]propionic acid.
1999,
Pubmed
,
Xenbase
Poulsen,
Evaluation of PhTX-74 as subtype-selective inhibitor of GluA2-containing AMPA receptors.
2014,
Pubmed
,
Xenbase
Ransom,
Cooperative modulation of [3H]MK-801 binding to the N-methyl-D-aspartate receptor-ion channel complex by L-glutamate, glycine, and polyamines.
1988,
Pubmed
Sagot,
Chemo-enzymatic synthesis of a series of 2,4-syn-functionalized (S)-glutamate analogues: new insight into the structure-activity relation of ionotropic glutamate receptor subtypes 5, 6, and 7.
2008,
Pubmed
Sills,
[3H]CGP 39653: a new N-methyl-D-aspartate antagonist radioligand with low nanomolar affinity in rat brain.
1991,
Pubmed
Sobolevsky,
X-ray structure, symmetry and mechanism of an AMPA-subtype glutamate receptor.
2009,
Pubmed
Traynelis,
Glutamate receptor ion channels: structure, regulation, and function.
2010,
Pubmed
Vogensen,
A stereochemical anomaly: the cyclised (R)-AMPA analogue (R)-3-hydroxy-4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridine-5-carboxylic acid [(R)-5-HPCA] resembles (S)-AMPA at glutamate receptors.
2004,
Pubmed
Wahl,
Antagonist properties of a phosphono isoxazole amino acid at glutamate R1-4 (R,S)-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid receptor subtypes.
1998,
Pubmed
,
Xenbase
