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130477-52-0

130477-52-0 | 9H-Imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid, 11,12,13,13a-tetrahydro-7-methoxy-9-oxo-, ethyl ester, (13aS)-

CAS No: 130477-52-0 Catalog No: AG000UGV MDL No:

Product Description

Catalog Number:
AG000UGV
Chemical Name:
9H-Imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid, 11,12,13,13a-tetrahydro-7-methoxy-9-oxo-, ethyl ester, (13aS)-
CAS Number:
130477-52-0
Molecular Formula:
C18H19N3O4
Molecular Weight:
341.3612
IUPAC Name:
ethyl (7S)-15-methoxy-12-oxo-2,4,11-triazatetracyclo[11.4.0.02,6.07,11]heptadeca-1(17),3,5,13,15-pentaene-5-carboxylate
InChI:
InChI=1S/C18H19N3O4/c1-3-25-18(23)15-16-14-5-4-8-20(14)17(22)12-9-11(24-2)6-7-13(12)21(16)10-19-15/h6-7,9-10,14H,3-5,8H2,1-2H3/t14-/m0/s1
InChI Key:
YKYOQIXTECBVBB-AWEZNQCLSA-N
SMILES:
CCOC(=O)c1ncn2c1[C@@H]1CCCN1C(=O)c1c2ccc(c1)OC

Properties

Complexity:
542  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0
Exact Mass:
341.138g/mol
Formal Charge:
0
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
341.367g/mol
Monoisotopic Mass:
341.138g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
73.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.8  

Literature

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α5GABAA receptors regulate hippocampal sharp wave-ripple activity in vitro. Neuropharmacology 20110301
Reducing excessive GABA-mediated tonic inhibition promotes functional recovery after stroke. Nature 20101111
Short-term memory impairment after isoflurane in mice is prevented by the α5 γ-aminobutyric acid type A receptor inverse agonist L-655,708. Anesthesiology 20101101
alpha5 Subunit-containing GABA(A) receptors mediate a slowly decaying inhibitory synaptic current in CA1 pyramidal neurons following Schaffer collateral activation. Neuropharmacology 20100301
Etomidate targets alpha5 gamma-aminobutyric acid subtype A receptors to regulate synaptic plasticity and memory blockade. Anesthesiology 20091101
Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum. Nature chemical biology 20091001
Effects of chronic exposure to an anabolic androgenic steroid cocktail on alpha5-receptor-mediated GABAergic transmission and neural signaling in the forebrain of female mice. Neuroscience 20090630
Imidazenil: a low efficacy agonist at alpha1- but high efficacy at alpha5-GABAA receptors fail to show anticonvulsant cross tolerance to diazepam or zolpidem. Neuropharmacology 20080801
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Alpha5GABAA receptors regulate the intrinsic excitability of mouse hippocampal pyramidal neurons. Journal of neurophysiology 20071001
Molecular basis for the GABAA receptor-mediated tonic inhibition in rat somatosensory cortex. Cerebral cortex (New York, N.Y. : 1991) 20070801
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L-655,708 enhances cognition in rats but is not proconvulsant at a dose selective for alpha5-containing GABAA receptors. Neuropharmacology 20061101
The proconvulsant effects of the GABAA alpha5 subtype-selective compound RY-080 may not be alpha5-mediated. European journal of pharmacology 20061024
Multiple and plastic receptors mediate tonic GABAA receptor currents in the hippocampus. The Journal of neuroscience : the official journal of the Society for Neuroscience 20051026
In vivo labelling of alpha5 subunit-containing GABA(A) receptors using the selective radioligand [(3)H]L-655,708. Neuropharmacology 20050801
Synthesis and biological evaluation of 3-heterocyclyl-7,8,9,10-tetrahydro-(7,10-ethano)-1,2,4-triazolo[3,4-a]phthalazines and analogues as subtype-selective inverse agonists for the GABA(A)alpha5 benzodiazepine binding site. Journal of medicinal chemistry 20040701
3-phenyl-6-(2-pyridyl)methyloxy-1,2,4-triazolo[3,4-a]phthalazines and analogues: high-affinity gamma-aminobutyric acid-A benzodiazepine receptor ligands with alpha 2, alpha 3, and alpha 5-subtype binding selectivity over alpha 1. Journal of medicinal chemistry 20040325
Synthesis, in vitro affinity, and efficacy of a bis 8-ethynyl-4H-imidazo[1,5a]- [1,4]benzodiazepine analogue, the first bivalent alpha5 subtype selective BzR/GABA(A) antagonist. Journal of medicinal chemistry 20031218
Anxiogenic-like activity of L-655,708, a selective ligand for the benzodiazepine site of GABA(A) receptors which contain the alpha-5 subunit, in the elevated plus-maze test. Progress in neuro-psychopharmacology & biological psychiatry 20021201
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells. The Journal of biological chemistry 20020419
Identification of amino acid residues responsible for the alpha5 subunit binding selectivity of L-655,708, a benzodiazepine binding site ligand at the GABA(A) receptor. Journal of neurochemistry 20010401
Evaluation of native GABA(A) receptors containing an alpha 5 subunit. European journal of pharmacology 20010209
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