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161230-88-2

161230-88-2 | 1H-Indole-2-carboxylic acid, 3-[(1E)-2-carboxy-2-phenylethenyl]-4,6-dichloro-

CAS No: 161230-88-2 Catalog No: AG001S9J MDL No:MFCD00935266

Product Description

Catalog Number:
AG001S9J
Chemical Name:
1H-Indole-2-carboxylic acid, 3-[(1E)-2-carboxy-2-phenylethenyl]-4,6-dichloro-
CAS Number:
161230-88-2
Molecular Formula:
C18H11Cl2NO4
Molecular Weight:
376.1902
MDL Number:
MFCD00935266
IUPAC Name:
3-[(E)-2-carboxy-2-phenylethenyl]-4,6-dichloro-1H-indole-2-carboxylic acid
InChI:
InChI=1S/C18H11Cl2NO4/c19-10-6-13(20)15-12(16(18(24)25)21-14(15)7-10)8-11(17(22)23)9-4-2-1-3-5-9/h1-8,21H,(H,22,23)(H,24,25)/b11-8+
InChI Key:
LPWVUDLZUVBQGP-DHZHZOJOSA-N
SMILES:
Clc1cc(Cl)c2c(c1)[nH]c(c2/C=C(\c1ccccc1)/C(=O)O)C(=O)O

Properties

Complexity:
561  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
1  
Exact Mass:
375.007g/mol
Formal Charge:
0
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
376.189g/mol
Monoisotopic Mass:
375.007g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
90.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4.8  

Literature

Title Journal
Increased expression of the NR2A NMDA receptor subunit in the prefrontal cortex of rats reared in isolation. Synapse (New York, N.Y.) 20091001
Abnormal glutamate receptor expression in the medial temporal lobe in schizophrenia and mood disorders. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20070901
CoMFA, synthesis, and pharmacological evaluation of (E)-3-(2-carboxy-2-arylvinyl)-4,6-dichloro-1H-indole-2-carboxylic acids: 3-[2-(3-aminophenyl)-2-carboxyvinyl]-4,6-dichloro-1H-indole-2-carboxylic acid, a potent selective glycine-site NMDA receptor antagonist. Journal of medicinal chemistry 20050224
An antisense oligonucleotide to the N-methyl-D-aspartate (NMDA) subunit NMDAR1 attenuates NMDA-induced nociception, hyperalgesia, and morphine tolerance. The Journal of pharmacology and experimental therapeutics 20050201
Model structures of the N-methyl-D-aspartate receptor subunit NR1 explain the molecular recognition of agonist and antagonist ligands. Journal of structural biology 20040301
Variations of acidic functions at position 2 and substituents at positions 4, 5 and 6 of the indole moiety and their effect on NMDA-glycine site affinity. European journal of medicinal chemistry 20031001
Expression of a soluble glycine binding domain of the NMDA receptor in Escherichia coli. Biochemical and biophysical research communications 20030606
Inhibition by theanine of binding of [3H]AMPA, [3H]kainate, and [3H]MDL 105,519 to glutamate receptors. Bioscience, biotechnology, and biochemistry 20021201
Radioligand binding assays for the glycine site on N-methyl-D-aspartate receptors. Current protocols in pharmacology 20020801
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells. The Journal of biological chemistry 20020419
4-Hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b] pyrimidine derivatives: synthesis and their biological evaluation for the glycine site acting on the N-methyl-D-aspartate (NMDA) receptor. Archives of pharmacal research 20010801
Ontogeny of ionotropic glutamate receptor expression in human fetal brain. Brain research. Developmental brain research 20010430
NMDA recepter-mediated neuroprotection by essential oils from the rhizomes of Acorus gramineus. Life sciences 20010216
Characterization of the binding of two novel glycine site antagonists to cloned NMDA receptors: evidence for two pharmacological classes of antagonists. British journal of pharmacology 20000501
[3H]MDL 105,519 binds with equal high affinity to both assembled and unassembled NR1 subunits of the NMDA receptor. European journal of pharmacology 19980717

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