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143691-37-6 | Ethanone, 1-[5-(4-aminophenyl)-8,9-dihydro-8-methyl-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-7-yl]-
CAS No: 143691-37-6 Catalog No: AG001I68 MDL No:
Product Description
Catalog Number:
AG001I68
Chemical Name:
Ethanone, 1-[5-(4-aminophenyl)-8,9-dihydro-8-methyl-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-7-yl]-
CAS Number:
143691-37-6
Molecular Formula:
C19H19N3O3
Molecular Weight:
337.3725
IUPAC Name:
1-[5-(4-aminophenyl)-8-methyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-7-yl]ethanone
InChI:
InChI=1S/C19H19N3O3/c1-11-7-14-8-17-18(25-10-24-17)9-16(14)19(21-22(11)12(2)23)13-3-5-15(20)6-4-13/h3-6,8-9,11H,7,10,20H2,1-2H3
InChI Key:
JACAAXNEHGBPOQ-UHFFFAOYSA-N
SMILES:
Nc1ccc(cc1)C1=NN(C(=O)C)C(Cc2c1cc1OCOc1c2)C
Properties
Complexity:
544
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
337.143g/mol
Formal Charge:
0
Heavy Atom Count:
25
Hydrogen Bond Acceptor Count:
5
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
337.379g/mol
Monoisotopic Mass:
337.143g/mol
Rotatable Bond Count:
1
Topological Polar Surface Area:
77.2A^2
Undefined Atom Stereocenter Count:
1
Undefined Bond Stereocenter Count:
0
XLogP3:
2.7
Literature
| Title | Journal |
|---|---|
| Mechanism of inhibition of the GluA2 AMPA receptor channel opening by talampanel and its enantiomer: the stereochemistry of the 4-methyl group on the diazepine ring of 2,3-benzodiazepine derivatives. | ACS chemical neuroscience 20130417 |
| Current trends in targeted therapies for glioblastoma multiforme. | Neurology research international 20120101 |
| Talampanel reduces the level of motoneuronal calcium in transgenic mutant SOD1 mice only if applied presymptomatically. | Amyotrophic lateral sclerosis : official publication of the World Federation of Neurology Research Group on Motor Neuron Diseases 20110901 |
| Glutamate and the biology of gliomas. | Glia 20110801 |
| Glioblastoma: changing expectations? | Clinical & translational oncology : official publication of the Federation of Spanish Oncology Societies and of the National Cancer Institute of Mexico 20110401 |
| An integrative view of mechanisms underlying generalized spike-and-wave epileptic seizures and its implication on optimal therapeutic treatments. | PloS one 20110101 |
| Clinical trials for neuroprotection in ALS. | CNS & neurological disorders drug targets 20100701 |
| A phase II trial of talampanel in subjects with amyotrophic lateral sclerosis. | Amyotrophic lateral sclerosis : official publication of the World Federation of Neurology Research Group on Motor Neuron Diseases 20100503 |
| Survival of patients with newly diagnosed glioblastoma treated with radiation and temozolomide in research studies in the United States. | Clinical cancer research : an official journal of the American Association for Cancer Research 20100415 |
| Phase 2 trial of talampanel, a glutamate receptor inhibitor, for adults with recurrent malignant gliomas. | Cancer 20100401 |
| Talampanel with standard radiation and temozolomide in patients with newly diagnosed glioblastoma: a multicenter phase II trial. | Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20090901 |
| [New roles of glutamate receptors in glias and gliomas]. | Brain and nerve = Shinkei kenkyu no shinpo 20090701 |
| Talampanel suppresses the acute and chronic effects of seizures in a rodent neonatal seizure model. | Epilepsia 20090401 |
| Enantioselective, ketoreductase-based entry into pharmaceutical building blocks: ethanol as tunable nicotinamide reductant. | Organic letters 20090115 |
| Amyotrophic lateral sclerosis. | Orphanet journal of rare diseases 20090101 |
| Third-generation antiepileptic drugs: mechanisms of action, pharmacokinetics and interactions. | Pharmacological reports : PR 20090101 |
| Current and emerging treatments for amyotrophic lateral sclerosis. | Neuropsychiatric disease and treatment 20090101 |
| Gateways to clinical trials. | Methods and findings in experimental and clinical pharmacology 20081001 |
| Early alterations of AMPA receptors mediate synaptic potentiation induced by neonatal seizures. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20080806 |
| Modifications of antiepileptic drugs for improved tolerability and efficacy. | Perspectives in medicinal chemistry 20080101 |
| Neuroprotective and anticonvulsant effects of EGIS-8332, a non-competitive AMPA receptor antagonist, in a range of animal models. | British journal of pharmacology 20070901 |
| [Dyskinesia in Parkinson's disease--major clinical features, aetiology, therapy]. | Fortschritte der Neurologie-Psychiatrie 20070701 |
| Rasagiline - a novel MAO B inhibitor in Parkinson's disease therapy. | Therapeutics and clinical risk management 20070601 |
| Effects of 2,3-benzodiazepine AMPA receptor antagonists on dopamine turnover in the striatum of rats with experimental parkinsonism. | Brain research bulletin 20070315 |
| [A new aspect in the research on antiepileptic drugs]. | Nihon yakurigaku zasshi. Folia pharmacologica Japonica 20070201 |
| Progress report on new antiepileptic drugs: a summary of the Eigth Eilat Conference (EILAT VIII). | Epilepsy research 20070101 |
| Talampanel. | Neurotherapeutics : the journal of the American Society for Experimental NeuroTherapeutics 20070101 |
| Gateways to clinical trials. | Methods and findings in experimental and clinical pharmacology 20061001 |
| Novel potent anticonvulsant agent containing a tetrahydroisoquinoline skeleton. | Journal of medicinal chemistry 20060907 |
| Talampanel a non-competitive AMPA-antagonist attenuates caspase-3 dependent apoptosis in mouse brain after transient focal cerebral ischemia. | Brain research bulletin 20060731 |
| Neuroprotective agents for clinical trials in ALS: a systematic assessment. | Neurology 20060711 |
| 3D pharmacophore models for 1,2,3,4-tetrahydroisoquinoline derivatives acting as anticonvulsant agents. | Archiv der Pharmazie 20060701 |
| Diverse mechanisms of antiepileptic drugs in the development pipeline. | Epilepsy research 20060601 |
| New antiepileptic drugs that are second generation to existing antiepileptic drugs. | Expert opinion on investigational drugs 20060601 |
| Influence of the N-acetylation polymorphism on the metabolism of talampanel: an investigation in fasted and fed subjects genotyped for NAT2 variants. | Die Pharmazie 20060201 |
| Talampanel improves the functional deficit after transient focal cerebral ischemia in rats. A 30-day follow up study. | Brain research bulletin 20060115 |
| Gateways to clinical trials. | Methods and findings in experimental and clinical pharmacology 20060101 |
| The effects of AMPA receptor antagonists in models of stroke and neurodegeneration. | European journal of pharmacology 20050905 |
| New features in synthesis of talampanel related 2,3-benzodiazepines. | Medicinal chemistry (Shariqah (United Arab Emirates)) 20050901 |
| Unified pharmacogenetics-based parent-metabolite pharmacokinetic model incorporating acetylation polymorphism for talampanel in humans. | Journal of pharmacokinetics and pharmacodynamics 20050801 |
| The AMPA-antagonist talampanel is neuroprotective in rodent models of focal cerebral ischemia. | Brain research bulletin 20050715 |
| Gateways to clinical trials. | Methods and findings in experimental and clinical pharmacology 20050101 |
| Treatment of Parkinson's disease : what's on the horizon? | CNS drugs 20050101 |
| Influence of the combined treatment of LY 300164 (an AMPA/kainate receptor antagonist) with adenosine receptor agonists on the electroconvulsive threshold in mice. | European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20041001 |
| Drugs in development for Parkinson's disease. | Current opinion in investigational drugs (London, England : 2000) 20040701 |
| Effect of two noncompetitive AMPA receptor antagonists GYKI 52466 and GYKI 53405 on vigilance, behavior and spike-wave discharges in a genetic rat model of absence epilepsy. | Brain research 20040522 |
| Omeprazole and talampanel as two examples of retrometabolic drug design. | Die Pharmazie 20040501 |
| Synthesis and anticonvulsant properties of tetrahydroisoquinoline derivatives. | Farmaco (Societa chimica italiana : 1989) 20040101 |
| AMPA receptor blockade potentiates the stimulatory effect of L-DOPA on dopamine release in dopamine-deficient corticostriatal slice preparation. | Critical reviews in neurobiology 20040101 |
| Is a hypothermic effect of LY300164, valproate and phenobarbital evident in mice? | Roczniki Akademii Medycznej w Bialymstoku (1995) 20040101 |
| Influence of LY 300164 alone or in combination with carbamazepine or diphenylhydantoin on the body temperature in mice. | Annales Universitatis Mariae Curie-Sklodowska. Sectio D: Medicina 20040101 |
| Synthesis and evaluation of pharmacological properties of novel annelated 2,3-benzodiazepine derivatives. | Journal of medicinal chemistry 20030814 |
| Discovery of a novel and highly potent noncompetitive AMPA receptor antagonist. | Journal of medicinal chemistry 20030102 |
| Talampanel, a new antiepileptic drug: single- and multiple-dose pharmacokinetics and initial 1-week experience in patients with chronic intractable epilepsy. | Epilepsia 20030101 |
| Influence of LY 300164, an AMPA/kainate receptor antagonist upon the anticonvulsant action of antiepileptic drugs against aminophylline-induced seizures in mice. | Polish journal of pharmacology 20030101 |
| Gateways to clinical trials. | Methods and findings in experimental and clinical pharmacology 20030101 |
| Influence of several convulsants on the protective activity of a non-competitive AMPA/kainate antagonist, LY 300164, and lamotrigine against maximal electroshock in mice. | Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20021201 |
| Protective effect of the antiepileptic drug candidate talampanel against AMPA-induced striatal neurotoxicity in neonatal rats. | Brain research bulletin 20021015 |
| Novel anticonvulsant medications in development. | Expert opinion on investigational drugs 20021001 |
| Progress report on new antiepileptic drugs: a summary of the Sixth Eilat Conference (EILAT VI). | Epilepsy research 20020901 |
| Influence of agents affecting voltage-dependent calcium channels and dantrolene on the anticonvulsant action of the AMPA/kainate receptor antagonist LY 300164 in mice. | European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20020801 |
| Na(+) entry through AMPA receptors results in voltage-gated k(+) channel blockade in cultured rat spinal cord motoneurons. | Journal of neurophysiology 20020801 |
| A crossover, add-on trial of talampanel in patients with refractory partial seizures. | Neurology 20020611 |
| Non-competitive AMPA antagonists of 2,3-benzodiazepine type. | Current pharmaceutical design 20020101 |
| AMPA and GABA(B) receptor antagonists and their interaction in rats with a genetic form of absence epilepsy. | European journal of pharmacology 20011102 |
| Talampanel, a novel noncompetitive AMPA antagonist, is neuroprotective after traumatic brain injury in rats. | Journal of neurotrauma 20011001 |
| Comparison of anticonvulsive and acute neuroprotective activity of three 2,3-benzodiazepine compounds, GYKI 52466, GYKI 53405, and GYKI 53655. | Brain research bulletin 20010601 |
| A kainate receptor increases the efficacy of GABAergic synapses. | Neuron 20010501 |
| Future prospects for the drug treatment of epilepsy. | CNS drugs 20010101 |
| AMPA receptor blockade improves levodopa-induced dyskinesia in MPTP monkeys. | Neurology 20000425 |
| Influence of LY 300164, an antagonist of AMPA/kainate receptors, on the anticonvulsant activity of clonazepam. | European journal of pharmacology 19990910 |
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