Synthesis and preliminary pharmacological evaluation of the four stereoisomers of (2S)-2-(2′-phosphono-3′-phenylcyclopropyl)glycine, the first class of 3′-substituted transC1′−2′-2-(2′-phosphonocyclopropyl)glycines

Bioorganic & Medicinal Chemistry
2007.0

Abstract

Four stereoisomers of (2S)-2-(2'-phosphono-3'-phenylcyclopropyl)glycine were synthesized by a stereocontrolled synthetic procedure and evaluated as mGluRs ligands. The (2S,1'R,2'S,3'R)-isomer (PPCG-2) showed to be a group III mGluRs selective ligand endowed with a moderate potency as mGluR4/mGluR6 agonist.

Knowledge Graph

Similar Paper

Synthesis and preliminary pharmacological evaluation of the four stereoisomers of (2S)-2-(2′-phosphono-3′-phenylcyclopropyl)glycine, the first class of 3′-substituted transC1′−2′-2-(2′-phosphonocyclopropyl)glycines
Bioorganic & Medicinal Chemistry 2007.0
Synthesis and preliminary biological evaluation of (2S,1′R,2′S)- and (2S,1′S,2′R)-2-(2′-phosphonocyclopropyl)glycines, two novel conformationally constrained l-AP4 analogues
Bioorganic & Medicinal Chemistry Letters 2006.0
Synthesis and studies on the mGluR agonist activity of FAP4 stereoisomers
Bioorganic & Medicinal Chemistry Letters 2015.0
(2S,1‘S,2‘R,3‘R)-2-(2‘-Carboxy-3‘-hydroxymethylcyclopropyl) Glycine Is a Highly Potent Group 2 and 3 Metabotropic Glutamate Receptor Agonist with Oral Activity
Journal of Medicinal Chemistry 2004.0
Synthesis, molecular modeling and preliminary biological evaluation of 1-amino-3-phosphono-3-cyclopentene-1-carboxylic acid and 1-amino-3-phosphono-2-cyclopentene-1-carboxylic acid, two novel agonists of metabotropic glutamate receptors of group III
Bioorganic & Medicinal Chemistry Letters 2000.0
Design, synthesis and preliminary evaluation of novel 3′-Substituted carboxycyclopropylglycines as antagonists at group 2 metabotropic glutamate receptors
Bioorganic & Medicinal Chemistry Letters 2001.0
A highly selective agonist for the metabotropic glutamate receptor mGluR2
MedChemComm 2011.0
(2S,1‘S,2‘S,3‘R)-2-(2‘-Carboxy-3‘-methylcyclopropyl) Glycine Is a Potent and Selective Metabotropic Group 2 Receptor Agonist with Anxiolytic Properties
Journal of Medicinal Chemistry 2002.0
Syntheses and Conformational Analyses of Glutamate Analogs:  2-(2-Carboxy-3-substituted-cyclopropyl)glycines as Useful Probes for Excitatory Amino Acid Receptors
Journal of Medicinal Chemistry 1996.0
Synthesis and Resolution ofcis-(±)-Methyl (1R,2S/1S,2R)-2-[(4-Hydroxy-4-phenylpiperidin-1-yl)methyl]-1-(4-methylphenyl)cyclopropanecarboxylate [(±)-PPCC)]: New σ Receptor Ligands with Neuroprotective Effect
Journal of Medicinal Chemistry 2010.0