Home Amines 147782-19-2
147782-19-2,MFCD00673968
Catalog No.:AA001F4G

147782-19-2 | 1,2-Cyclopropanedicarboxylic acid, 3-[(S)-aminocarboxymethyl]-, (1R,2R)-

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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA001F4G
Chemical Name:
1,2-Cyclopropanedicarboxylic acid, 3-[(S)-aminocarboxymethyl]-, (1R,2R)-
CAS Number:
147782-19-2
Molecular Formula:
C7H9NO6
Molecular Weight:
203.1495
MDL Number:
MFCD00673968
SMILES:
N[C@@H](C1[C@H]([C@@H]1C(=O)O)C(=O)O)C(=O)O
Properties
Computed Properties
 
Complexity:
281  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Heavy Atom Count:
14  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
4  
XLogP3:
-4.3  

Literature

Title: Pharmacological characterization of JNJ-40068782, a new potent, selective, and systemically active positive allosteric modulator of the mGlu2 receptor and its radioligand [3H]JNJ-40068782.

Journal: The Journal of pharmacology and experimental therapeutics 20130901

Title: Functional and pharmacological characteristics of metabotropic glutamate receptors 2/4 heterodimers.

Journal: Molecular pharmacology 20120901

Title: M2 muscarinic acetylcholine receptors regulate long-term potentiation at hippocampal CA3 pyramidal cell synapses in an input-specific fashion.

Journal: Journal of neurophysiology 20120701

Title: Noradrenaline-induced enhancement of oscillatory local field potentials in the mouse accessory olfactory bulb does not depend on disinhibition of mitral cells.

Journal: The European journal of neuroscience 20120501

Title: Upregulation of presynaptic mGluR2, but not mGluR3 in the epileptic medial perforant path.

Journal: Neuropharmacology 20120301

Title: Group II metabotropic glutamate receptors depress synaptic transmission onto subicular burst firing neurons.

Journal: PloS one 20120101

Title: High affinity group III mGluRs regulate mossy fiber input to CA3 interneurons.

Journal: Hippocampus 20111201

Title: Study of novel selective mGlu2 agonist in the temporo-ammonic input to CA1 neurons reveals reduced mGlu2 receptor expression in a Wistar substrain with an anxiety-like phenotype.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20110504

Title: Functional plasticity of group II metabotropic glutamate receptors in regulating spinal excitatory and inhibitory synaptic input in neuropathic pain.

Journal: The Journal of pharmacology and experimental therapeutics 20110101

Title: Selective Interactions of Valeriana officinalis Extracts and Valerenic Acid with [H]Glutamate Binding to Rat Synaptic Membranes.

Journal: Evidence-based complementary and alternative medicine : eCAM 20110101

Title: Striatal ablation of GABAergic neurons prevents the in vivo neuroprotective effect of DCG-IV against the MPP+-induced neurotoxicity on dopaminergic nerve terminals.

Journal: Neurochemistry international 20101201

Title: Distinct modes of modulation of GABAergic transmission by Group I metabotropic glutamate receptors in rat entorhinal cortex.

Journal: Hippocampus 20100801

Title: Modulators of metabotropic glutamate receptors microinfused into perirhinal cortex: anticonvulsant effects in rats challenged with soman.

Journal: European journal of pharmacology 20100625

Title: Munc13-2 differentially affects hippocampal synaptic transmission and plasticity.

Journal: Cerebral cortex (New York, N.Y. : 1991) 20100501

Title: Frequency facilitation at mossy fiber-CA3 synapses of freely behaving rats contributes to the induction of persistent LTD via an adenosine-A1 receptor-regulated mechanism.

Journal: Cerebral cortex (New York, N.Y. : 1991) 20100501

Title: A virtual screening hit reveals new possibilities for developing group III metabotropic glutamate receptor agonists.

Journal: Journal of medicinal chemistry 20100408

Title: Metabotropic glutamate receptors in median preoptic neurons modulate neuronal excitability and glutamatergic and GABAergic inputs from the subfornical organ.

Journal: Journal of neurophysiology 20100201

Title: Involvement of Group II mGluRs in mossy fiber LTD.

Journal: Synapse (New York, N.Y.) 20091201

Title: Neuroprotective effects of group II metabotropic glutamate receptor agonist DCG-IV on hippocampal neurons in transient forebrain ischemia.

Journal: Neuroscience letters 20090925

Title: Activation of metabotropic glutamate receptor type 2/3 supports the involvement of the hippocampal mossy fiber pathway on contextual fear memory consolidation.

Journal: Learning & memory (Cold Spring Harbor, N.Y.) 20090801

Title: Unique response of zinc in the hippocampus to behavioral stress and attenuation of subsequent mossy fiber long-term potentiation.

Journal: Neurotoxicology 20090701

Title: Role of glutamate autoreceptors at hippocampal mossy fiber synapses.

Journal: Neuron 20081226

Title: Bidirectional Hebbian plasticity at hippocampal mossy fiber synapses on CA3 interneurons.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20081224

Title: Impaired expression and function of group II metabotropic glutamate receptors in pilocarpine-treated chronically epileptic rats.

Journal: Brain research 20081113

Title: Satellite NG2 progenitor cells share common glutamatergic inputs with associated interneurons in the mouse dentate gyrus.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20080723

Title: The role of NMDA receptors in regulating group II metabotropic glutamate receptor-mediated long-term depression in rat medial prefrontal cortex.

Journal: Neuropharmacology 20080601

Title: Frequency facilitation at mossy fiber-CA3 synapses of freely behaving rats is regulated by adenosine A1 receptors.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20080430

Title: Mechanisms of microglia-mediated neurotoxicity in a new model of the stroke penumbra.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20080227

Title: Alpha-CaMKII deficiency causes immature dentate gyrus, a novel candidate endophenotype of psychiatric disorders.

Journal: Molecular brain 20080101

Title: Activator protein-1 responsive to the group II metabotropic glutamate receptor subtype in association with intracellular calcium in cultured rat cortical neurons.

Journal: Neurochemistry international 20071201

Title: A selective positive allosteric modulator of metabotropic glutamate receptor subtype 2 blocks a hallucinogenic drug model of psychosis.

Journal: Molecular pharmacology 20070801

Title: Group II metabotropic glutamate receptors inhibit glutamate release at thalamocortical synapses in the developing somatosensory cortex.

Journal: Neuroscience 20070525

Title: GABAergic interneurons facilitate mossy fiber excitability in the developing hippocampus.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20070207

Title: Metabotropic glutamate receptors differentially regulate GABAergic inhibition in thalamus.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20061227

Title: Mechanisms of glutamate receptor induced proliferation of astrocytes.

Journal: Neuroreport 20061218

Title: Metabotropic glutamate receptor antagonists and agonists: potential neuroprotectors in diffuse brain injury.

Journal: Journal of clinical neuroscience : official journal of the Neurosurgical Society of Australasia 20061201

Title: Compartmentalized Ca(2+) channel regulation at divergent mossy-fiber release sites underlies target cell-dependent plasticity.

Journal: Neuron 20061109

Title: Activation of Group II/III metabotropic glutamate receptors attenuates LPS-induced astroglial neurotoxicity via promoting glutamate uptake.

Journal: Journal of neuroscience research 20060801

Title: Selective inhibition of spontaneous but not Ca2+ -dependent release machinery by presynaptic group II mGluRs in rat cerebellar slices.

Journal: Journal of neurophysiology 20060701

Title: Activation of receptors negatively coupled to adenylate cyclase is required for induction of long-term synaptic depression at Schaffer collateral-CA1 synapses.

Journal: Journal of neurobiology 20060215

Title: A similar impairment in CA3 mossy fibre LTP in the R6/2 mouse model of Huntington's disease and in the complexin II knockout mouse.

Journal: The European journal of neuroscience 20051001

Title: Presynaptic inhibition of corticothalamic feedback by metabotropic glutamate receptors.

Journal: Journal of neurophysiology 20050701

Title: Metabotropic glutamate 2 receptor potentiators: receptor modulation, frequency-dependent synaptic activity, and efficacy in preclinical anxiety and psychosis model(s).

Journal: Psychopharmacology 20050401

Title: The role of extracellular adenosine in regulating mossy fiber synaptic plasticity.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20050316

Title: Stimulation of microglial metabotropic glutamate receptor mGlu2 triggers tumor necrosis factor alpha-induced neurotoxicity in concert with microglial-derived Fas ligand.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20050316

Title: Divergent regulatory mechanisms governing BDNF mRNA expression in cerebral cortex and substantia nigra in response to striatal target ablation.

Journal: Experimental neurology 20050301

Title: Activation of group II metabotropic glutamate receptors induces depotentiation in amygdala slices and reduces fear-potentiated startle in rats.

Journal: Learning & memory (Cold Spring Harbor, N.Y.) 20050301

Title: Enhancement of glutamate uptake mediates the neuroprotection exerted by activating group II or III metabotropic glutamate receptors on astrocytes.

Journal: Journal of neurochemistry 20050201

Title: Metabotropic glutamate receptor 2 modulates excitatory synaptic transmission in the rat globus pallidus.

Journal: Neuropharmacology 20050101

Title: Metabotropic glutamate receptors modulate feedback inhibition in a developmentally regulated manner in rat dentate gyrus.

Journal: The Journal of physiology 20041201

Title: Activation of metabotropic glutamate receptors does not alter the phosphorylation state of GluR1 AMPA receptor subunit at serine 845 in perirhinal cortical neurons.

Journal: Neuroscience letters 20041130

Title: Assessing the role of GLUK5 and GLUK6 at hippocampal mossy fiber synapses.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20041110

Title: Measurement of presynaptic zinc changes in hippocampal mossy fibers.

Journal: Brain research 20041105

Title: L-CCG-I activates group III metabotropic glutamate receptors in the hippocampal CA3 region.

Journal: Neuropharmacology 20040801

Title: Metabotropic glutamate and dopamine receptors co-regulate AMPA receptor activity through PKA in cultured chick retinal neurones: effect on GluR4 phosphorylation and surface expression.

Journal: Journal of neurochemistry 20040801

Title: AMPA receptor-mediated presynaptic inhibition at cerebellar GABAergic synapses: a characterization of molecular mechanisms.

Journal: The European journal of neuroscience 20040501

Title: Photolysis of postsynaptic caged Ca2+ can potentiate and depress mossy fiber synaptic responses in rat hippocampal CA3 pyramidal neurons.

Journal: Journal of neurophysiology 20040401

Title: An NMDAR-independent LTP mediated by group II metabotropic glutamate receptors and p42/44 MAP kinase in the dentate gyrus in vitro.

Journal: Neuropharmacology 20040301

Title: In vivo modulation of extracellular hippocampal glutamate and GABA levels and limbic seizures by group I and II metabotropic glutamate receptor ligands.

Journal: Journal of neurochemistry 20040301

Title: Glutamate release increases during mossy-CA3 LTP but not during Schaffer-CA1 LTP.

Journal: The European journal of neuroscience 20040301

Title: Modulation of rhythmic patterns and cumulative depolarization by group I metabotropic glutamate receptors in the neonatal rat spinal cord in vitro.

Journal: The European journal of neuroscience 20040201

Title: Inhibitory effects of group II mGluR-related drugs on memory performance in mice.

Journal: Physiology & behavior 20040201

Title: (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: Journal of medicinal chemistry 20040115

Title: Quantal transmission at mossy fibre targets in the CA3 region of the rat hippocampus.

Journal: The Journal of physiology 20040101

Title: The role of AMPA and metabotropic glutamate receptors on morphine withdrawal in infant rats.

Journal: International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience 20040101

Title: Group II metabotropic glutamate receptor modulation of excitatory transmission in rat subthalamic nucleus.

Journal: The Journal of physiology 20031201

Title: Pharmacological characterization and identification of amino acids involved in the positive modulation of metabotropic glutamate receptor subtype 2.

Journal: Molecular pharmacology 20031001

Title: Molecular modeling and mutagenesis of the ligand-binding pocket of the mGlu3 subtype of metabotropic glutamate receptor.

Journal: Journal of neurochemistry 20030801

Title: Reexamination of the role of hyperpolarization-activated cation channels in short- and long-term plasticity at hippocampal mossy fiber synapses.

Journal: Neuropharmacology 20030601

Title: Expression and functional role of mGluR3 and mGluR5 in human astrocytes and glioma cells: opposite regulation of glutamate transporter proteins.

Journal: The European journal of neuroscience 20030501

Title: Reduction of excitatory postsynaptic responses by persistently active metabotropic glutamate receptors in the hippocampus.

Journal: Journal of neurophysiology 20030401

Title: Associative mossy fibre LTP induced by pairing presynaptic stimulation with postsynaptic hyperpolarization of CA3 neurons in rat hippocampal slice.

Journal: The European journal of neuroscience 20030401

Title: Functional metabotropic glutamate receptors are expressed in oligodendrocyte progenitor cells.

Journal: Journal of neurochemistry 20030301

Title: Baseline glutamate levels affect group I and II mGluRs in layer V pyramidal neurons of rat sensorimotor cortex.

Journal: Journal of neurophysiology 20030301

Title: Direct and indirect interactions between cannabinoid CB1 receptor and group II metabotropic glutamate receptor signalling in layer V pyramidal neurons from the rat prefrontal cortex.

Journal: The European journal of neuroscience 20030301

Title: Modulation of epileptiform burst frequency by the metabotropic glutamate receptor subtype mGluR3.

Journal: Epilepsy research 20030301

Title: Different roles of group I and group II metabotropic glutamate receptors on phencyclidine-induced dopamine release in the rat prefrontal cortex.

Journal: Neuroscience letters 20030123

Title: Mechanisms underlying the inhibition of long-term potentiation by preconditioning stimulation in the hippocampus in vitro.

Journal: Neuroscience 20030101

Title: The role of metabotropic glutamate receptors in regulation of striatal proenkephalin expression: implications for the therapy of Parkinson's disease.

Journal: Neuroscience 20030101

Title: Activation of glutamate transporters in rods inhibits presynaptic calcium currents.

Journal: Visual neuroscience 20030101

Title: Effect of donepezil on group II mGlu receptor agonist- or antagonist-induced amnesia on passive avoidance in mice.

Journal: Neural plasticity 20030101

Title: Activation of group II mGlu receptors inhibits voltage-gated Ca2+ currents in myenteric neurons.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20021201

Title: Role for cAMP and protein phosphatase in the presynaptic expression of mouse hippocampal mossy fibre depotentiation.

Journal: The Journal of physiology 20020915

Title: Activation of brainstem metabotropic glutamate receptors inhibits spinal nociception in adult rats.

Journal: Pharmacology, biochemistry, and behavior 20020901

Title: Metabotropic and NMDA glutamate receptor interactions with osmotic stimuli in supraoptic neurons.

Journal: Pharmacology, biochemistry, and behavior 20020901

Title: (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: Journal of medicinal chemistry 20020815

Title: Group I and II metabotropic glutamate receptors modulate respiratory activity in the lamprey.

Journal: The European journal of neuroscience 20020801

Title: Common and selective molecular determinants involved in metabotopic glutamate receptor agonist activity.

Journal: Journal of medicinal chemistry 20020718

Title: Long-term depression induced by postsynaptic group II metabotropic glutamate receptors linked to phospholipase C and intracellular calcium rises in rat prefrontal cortex.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20020501

Title: Modulation of dendritic release of dopamine by metabotropic glutamate receptors in rat substantia nigra.

Journal: Biochemical pharmacology 20020401

Title: Distinct NMDA receptors provide differential modes of transmission at mossy fiber-interneuron synapses.

Journal: Neuron 20020314

Title: The cannabinoid CB1 receptor mediates retrograde signals for depolarization-induced suppression of inhibition in cerebellar Purkinje cells.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20020301

Title: Presynaptic group II metabotropic glutamate receptors reduce stimulated and spontaneous transmitter release in human dentate gyrus.

Journal: Neuropharmacology 20020301

Title: DCG-IV but not other group-II metabotropic receptor agonists induces microglial BDNF mRNA expression in the rat striatum. Correlation with neuronal injury.

Journal: Neuroscience 20020101

Title: The role of striatal metabotropic glutamate receptors in Parkinson's disease.

Journal: Amino acids 20020101

Title: Activation of group II metabotropic glutamate receptors inhibits glutamate release from salamander retinal photoreceptors.

Journal: Visual neuroscience 20020101

Title: Effects of metabotropic glutamate receptor agonists and antagonists on D-aspartate release from mouse cerebral cortical and striatal slices.

Journal: Neurochemical research 20011101

Title: Multiple G-protein-coupled receptors mediate presynaptic inhibition at single excitatory synapses in the rat visual cortex.

Journal: Neuroscience letters 20010824

Title: Neuroprotection afforded by NAAG and NAALADase inhibition requires glial cells and metabotropic glutamate receptor activation.

Journal: European journal of pharmacology 20010824

Title: Fast synaptic transmission mediated by P2X receptors in CA3 pyramidal cells of rat hippocampal slice cultures.

Journal: The Journal of physiology 20010815

Title: Attenuation of seizures induced by homocysteic acid in immature rats by metabotropic glutamate group II and group III receptor agonists.

Journal: Brain research 20010727

Title: Priming stimulation of group II metabotropic glutamate receptors inhibits the subsequent induction of rat hippocampal long-term depression in vitro.

Journal: Neuroscience letters 20010706

Title: Group II mGlu receptor agonists fail to protect against various neurotoxic insults induced in murine cortical, striatal and cerebellar granular pure neuronal cultures.

Journal: Neuropharmacology 20010701

Title: Metabotropic glutamate receptor subtypes modulating neurotransmission at parallel fibre-Purkinje cell synapses in rat cerebellum.

Journal: Neuropharmacology 20010701

Title: Infusion of the metabotropic receptor agonist, DCG-IV, into the main olfactory bulb induces olfactory preference learning in rat pups.

Journal: Brain research. Developmental brain research 20010629

Title: Presynaptic group II mGluR inhibition of short-term depression in the medial perforant path of the dentate gyrus in vitro.

Journal: Journal of neurophysiology 20010601

Title: The effect of groups II and III metabotropic glutamate receptor activation on neuronal injury in a rodent model of traumatic brain injury.

Journal: Neurosurgery 20010501

Title: Electrophysiological characterization of 'giant' cells in stratum radiatum of the CA3 hippocampal region.

Journal: Journal of neurophysiology 20010501

Title: Characterization with [3H]quisqualate of group I metabotropic glutamate receptor subtype in rat central and peripheral excitable tissues.

Journal: Neurochemistry international 20010301

Title: beta-NAAG rescues LTP from blockade by NAAG in rat dentate gyrus via the type 3 metabotropic glutamate receptor.

Journal: Journal of neurophysiology 20010301

Title: Pharmacology and neuroprotective actions of mGlu receptor ligands.

Journal: Developmental medicine and child neurology. Supplement 20010301

Title: Metabotropic glutamate receptors modulate GABA release from mouse hippocampal slices.

Journal: Neurochemical research 20010201

Title: Regional distribution and pharmacological characteristics of [3H]N-acetyl-aspartyl-glutamate (NAAG) binding sites in rat brain.

Journal: Neurochemistry international 20010101

Title: Group II metabotropic glutamate receptor activation protects striatal dopaminergic nerve terminals against MPP+-induced neurotoxicity along with brain-derived neurotrophic factor induction.

Journal: Journal of neurochemistry 20010101

Title: Metabotropic glutamate receptor 5 mediates the potentiation of N-methyl-D-aspartate responses in medium spiny striatal neurons.

Journal: Neuroscience 20010101

Title: Characterization of [(3)H]Quisqualate binding to recombinant rat metabotropic glutamate 1a and 5a receptors and to rat and human brain sections.

Journal: Journal of neurochemistry 20001201

Title: Binding of [3H](2S,1'S,2'S)-2-(9-xanthylmethyl)-2-(2'-carboxycyclopropyl) glycine ([3H]LY341495) to cell membranes expressing recombinant human group III metabotropic glutamate receptor subtypes.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20001201

Title: Characterization of [(3)H]-LY354740 binding to rat mGlu2 and mGlu3 receptors expressed in CHO cells using semliki forest virus vectors.

Journal: Neuropharmacology 20000724

Title: The group II metabotropic glutamate receptor agonist, DCG-IV, alleviates akinesia following intranigral or intraventricular administration in the reserpine-treated rat.

Journal: British journal of pharmacology 20000201

Title: [3H]-LY341495 as a novel antagonist radioligand for group II metabotropic glutamate (mGlu) receptors: characterization of binding to membranes of mGlu receptor subtype expressing cells.

Journal: Neuropharmacology 19991001

Title: Cloning and functional expression of alternative spliced variants of the human metabotropic glutamate receptor 8.

Journal: Brain research. Molecular brain research 19990420

Title: Comparative effect of L-CCG-I, DCG-IV and gamma-carboxy-L-glutamate on all cloned metabotropic glutamate receptor subtypes.

Journal: Neuropharmacology 19980801

Title: Characterization of [3H]-(2S,2'R,3'R)-2-(2',3'-dicarboxy-cyclopropyl)glycine ([3H]-DCG IV) binding to metabotropic mGlu2 receptor-transfected cell membranes.

Journal: British journal of pharmacology 19980201

Title: Neuron damage induced by some potent kainoids and neuroprotective action of new agonists for metabotropic glutamate receptors.

Journal: European neurology 19940101

Title: Brabet I, et al. Comparative effect of L-CCG-I, DCG-IV and gamma-carboxy-L-glutamate on all clonedmetabotropic glutamate receptor subtypes. Neuropharmacology. 1998 Aug;37(8):1043-51.

Title: Bertrand HO, et al. Common and selective molecular determinants involved in metabotopic glutamate receptoragonist activity. J Med Chem. 2002 Jul 18;45(15):3171-83.

Title: Uyama Y, et al. DCG-IV, a potent metabotropic glutamate receptor agonist, as an NMDA receptor agonist in the rat cortical slice. Brain Res. 1997 Mar 28;752(1-2):327-30.

Title: Tomita N, et al. The effects of DCG-IV and L-CCG-1 upon phencyclidine (PCP)-induced locomotion and behavioral changes in mice. Ann N Y Acad Sci. 2000 Sep;914:284-91.

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Tags:147782-19-2 Molecular Formula|147782-19-2 MDL|147782-19-2 SMILES|147782-19-2 1,2-Cyclopropanedicarboxylic acid, 3-[(S)-aminocarboxymethyl]-, (1R,2R)-