Synthesis of (3-hydroxy-pyrazolin-5-yl)glycine based ligands interacting with ionotropic glutamate receptors

European Journal of Medicinal Chemistry
2014.0

Abstract

Following the concept that increasing the molecular complexity may enhance the receptor selectivity, we replaced the 3-hydroxy-isoxazoline ring of model compound tricholomic acid with a 3-hydroxy-pyrazoline ring, which could be variously decorated at the N1 position, inserting groups characterized by different electronic and steric properties. Binding assays on rat brain synaptic membranes showed that, depending on the nature of the substituent, some of the new synthesized ligands interacted with either AMPA or KA receptors, with affinities in the mid-micromolar range.

Knowledge Graph

Similar Paper

Synthesis of (3-hydroxy-pyrazolin-5-yl)glycine based ligands interacting with ionotropic glutamate receptors
European Journal of Medicinal Chemistry 2014.0
Synthesis and Pharmacological Characterization at Glutamate Receptors of the Four Enantiopure Isomers of Tricholomic Acid
Journal of Medicinal Chemistry 2008.0
Use of the 4-Hydroxytriazole Moiety as a Bioisosteric Tool in the Development of Ionotropic Glutamate Receptor Ligands
Journal of Medicinal Chemistry 2019.0
3-Hydroxy-1H-quinazoline-2,4-dione derivatives as new antagonists at ionotropic glutamate receptors: Molecular modeling and pharmacological studies
European Journal of Medicinal Chemistry 2012.0
4-Hydroxy-1,2,5-oxadiazol-3-yl Moiety as Bioisoster of the Carboxy Function. Synthesis, Ionization Constants, and Molecular Pharmacological Characterization at Ionotropic Glutamate Receptors of Compounds Related to Glutamate and Its Homologues
Journal of Medicinal Chemistry 2010.0
Evaluation and synthesis of amino-hydroxy isoxazoles and pyrazoles as potential glycine agonists
Journal of Medicinal Chemistry 1989.0
Synthesis and Structure-Activity Studies on Acidic Amino Acids and Related Diacids as NMDA Receptor Ligands
Journal of Medicinal Chemistry 1994.0
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
Journal of Medicinal Chemistry 2008.0
N-Hydroxypyrazolyl Glycine Derivatives as SelectiveN-Methyl-<scp>d</scp>-aspartic Acid Receptor Ligands
Journal of Medicinal Chemistry 2008.0
Ibotenic Acid Analogues. Synthesis, Molecular Flexibility, and in Vitro Activity of Agonists and Antagonists at Central Glutamic Acid Receptors
Journal of Medicinal Chemistry 1985.0