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264218-23-7,MFCD04039789
Catalog No.:AA002T2I

264218-23-7 | 1H-Pyrrole-2,5-dione, 3-[(3-chloro-4-hydroxyphenyl)amino]-4-(2-nitrophenyl)-

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1mg
98%
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$12.00   $8.00
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10mg
98%
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$39.00   $28.00
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50mg
98%
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$126.00   $89.00
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA002T2I
Chemical Name:
1H-Pyrrole-2,5-dione, 3-[(3-chloro-4-hydroxyphenyl)amino]-4-(2-nitrophenyl)-
CAS Number:
264218-23-7
Molecular Formula:
C16H10ClN3O5
Molecular Weight:
359.7207
MDL Number:
MFCD04039789
SMILES:
O=C1NC(=O)C(=C1Nc1ccc(c(c1)Cl)O)c1ccccc1[N+](=O)[O-]
Properties
Computed Properties
 
Complexity:
617  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
3  
XLogP3:
2.8  

Literature

Title: PI3K/Akt/GSK3β induced CREB activation ameliorates arsenic mediated alterations in NMDA receptors and associated signaling in rat hippocampus: Neuroprotective role of curcumin.

Journal: Neurotoxicology 20180701

Title: Inhibitory Effects of Bisphenol-A on Neural Stem Cells Proliferation and Differentiation in the Rat Brain Are Dependent on Wnt/β-Catenin Pathway.

Journal: Molecular neurobiology 20151201

Title: Activation of β-catenin by inhibitors of glycogen synthase kinase-3 ameliorates cisplatin-induced cytotoxicity and pro-inflammatory cytokine expression in HEI-OC1 cells.

Journal: Toxicology 20140605

Title: Phosphorylation of amyloid precursor protein at threonine 668 is essential for its copper-responsive trafficking in SH-SY5Y neuroblastoma cells.

Journal: The Journal of biological chemistry 20140418

Title: Sirt1 inhibits the transcription factor CREB to regulate pituitary growth hormone synthesis.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20130401

Title: Roles of glycogen synthase kinase 3 in Alzheimer's disease.

Journal: Current Alzheimer research 20120901

Title: Ryanodine receptor blockade reduces amyloid-β load and memory impairments in Tg2576 mouse model of Alzheimer disease.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20120822

Title: Selectively silencing GSK-3 isoforms reduces plaques and tangles in mouse models of Alzheimer's disease.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20120523

Title: A pharmacologically-based array to identify targets of cyclosporine A-induced toxicity in cultured renal proximal tubule cells.

Journal: Toxicology and applied pharmacology 20120115

Title: Canonical WNT signaling enhances stem cell expression in the developing heart without a corresponding inhibition of cardiogenic differentiation.

Journal: Stem cells and development 20111101

Title: GSK3-mediated instability of tubulin polymers is responsible for the failure of immature CD4+CD8+ thymocytes to polarize their MTOC in response to TCR stimulation.

Journal: International immunology 20111101

Title: Development of a cellular tau enzyme-linked immunosorbent assay method for screening GSK-3β inhibitors.

Journal: Assay and drug development technologies 20111001

Title: GSK-3β inhibition promotes cell death, apoptosis, and in vivo tumor growth delay in neuroblastoma Neuro-2A cell line.

Journal: Journal of neuro-oncology 20110801

Title: GSK-3β: a signaling pathway node modulating neural stem cell and endothelial cell interactions.

Journal: Angiogenesis 20110501

Title: Deletion of glycogen synthase kinase-3β in cartilage results in up-regulation of glycogen synthase kinase-3α protein expression.

Journal: Endocrinology 20110501

Title: Eutypoids B-E produced by a Penicillium sp. strain from the North Sea.

Journal: Journal of natural products 20110128

Title: P27(Kip1), regulated by glycogen synthase kinase-3β, results in HMBA-induced differentiation of human gastric cancer cells.

Journal: BMC cancer 20110101

Title: Lithium promotes neural precursor cell proliferation: evidence for the involvement of the non-canonical GSK-3β-NF-AT signaling.

Journal: Cell & bioscience 20110101

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Regulation of GSK-3beta by calpain in the 3-nitropropionic acid model.

Journal: Hippocampus 20100801

Title: Role of glycogen synthase kinase 3 (GSK-3) in innate immune response of human immature dendritic cells to Aspergillus fumigatus.

Journal: Medical mycology 20100601

Title: Neurites regrowth of cortical neurons by GSK3beta inhibition independently of Nogo receptor 1.

Journal: Journal of neurochemistry 20100601

Title: GSK3 beta regulates myelin-dependent axon outgrowth inhibition through CRMP4.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20100421

Title: A new class of molecular targeted radioprotectors: GSK-3beta inhibitors.

Journal: International journal of radiation oncology, biology, physics 20100201

Title: Dependence of EGF-induced increases in corneal epithelial proliferation and migration on GSK-3 inactivation.

Journal: Investigative ophthalmology & visual science 20091001

Title: Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.

Journal: Nature chemical biology 20091001

Title: A molecular study of pathways involved in the inhibition of cell proliferation in neuroblastoma B65 cells by the GSK-3 inhibitors lithium and SB-415286.

Journal: Journal of cellular and molecular medicine 20090901

Title: Chronic lithium treatment up-regulates cell surface Na(V)1.7 sodium channels via inhibition of glycogen synthase kinase-3 in adrenal chromaffin cells: enhancement of Na(+) influx, Ca(2+) influx and catecholamine secretion after lithium withdrawal.

Journal: Neuropharmacology 20090901

Title: Fragment and knowledge-based design of selective GSK-3beta inhibitors using virtual screening models.

Journal: European journal of medicinal chemistry 20090601

Title: Deregulation of Tpl2 and NF-kappaB signaling and induction of macrophage apoptosis by the anti-depressant drug lithium.

Journal: Cellular signalling 20090401

Title: Glucocorticoids and lithium reciprocally regulate the proliferation of adult dentate gyrus-derived neural precursor cells through GSK-3beta and beta-catenin/TCF pathway.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20090201

Title: Glycogen synthase kinase-3 inhibitors augment TRAIL-induced apoptotic death in human hepatoma cells.

Journal: Biochemical pharmacology 20090101

Title: Mechanical strain inhibits adipogenesis in mesenchymal stem cells by stimulating a durable beta-catenin signal.

Journal: Endocrinology 20081201

Title: Enhanced glycogenesis is involved in cellular senescence via GSK3/GS modulation.

Journal: Aging cell 20081201

Title: Glycogen synthase kinase 3 inhibition slows mitochondrial adenine nucleotide transport and regulates voltage-dependent anion channel phosphorylation.

Journal: Circulation research 20081024

Title: Inactivation of glycogen synthase kinase 3 promotes axonal growth and recovery in the CNS.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20080903

Title: GSK-3 beta inhibition and prevention of mitochondrial apoptosis inducing factor release are not involved in the antioxidant properties of SB-415286.

Journal: European journal of pharmacology 20080707

Title: Pharmacophore modeling, quantitative structure-activity relationship analysis, and in silico screening reveal potent glycogen synthase kinase-3beta inhibitory activities for cimetidine, hydroxychloroquine, and gemifloxacin.

Journal: Journal of medicinal chemistry 20080410

Title: Neuroprotective effects of SB-415286 on hydrogen peroxide-induced cell death in B65 rat neuroblastoma cells and neurons.

Journal: International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience 20080101

Title: The selectivity of protein kinase inhibitors: a further update.

Journal: The Biochemical journal 20071215

Title: Glycogen synthase kinase 3 activity during development of bone marrow-derived dendritic cells (DCs) essential for the DC function to induce T helper 2 polarization.

Journal: Immunology 20071001

Title: Lithium desensitizes brain mitochondria to calcium, antagonizes permeability transition, and diminishes cytochrome C release.

Journal: The Journal of biological chemistry 20070622

Title: LTP inhibits LTD in the hippocampus via regulation of GSK3beta.

Journal: Neuron 20070301

Title: Inhibiting glycogen synthase kinase 3beta in sepsis.

Journal: Novartis Foundation symposium 20070101

Title: HaCaT keratinocyte migration is dependent on epidermal growth factor receptor signaling and glycogen synthase kinase-3alpha.

Journal: Experimental cell research 20060910

Title: A cellular assay for measuring the inhibition of glycogen synthase kinase-3 via the accumulation of beta-catenin in Chinese hamster ovary clone K1 cells.

Journal: Assay and drug development technologies 20060801

Title: Glycogen synthase kinase-3 acts upstream of ADP-ribosylation factor 6 and Rac1 to regulate epithelial cell migration.

Journal: Experimental cell research 20060515

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Mechanical and chemical regulation of endothelial cell polarity.

Journal: Circulation research 20060414

Title: Reduction of experimental colitis in the rat by inhibitors of glycogen synthase kinase-3beta.

Journal: British journal of pharmacology 20060301

Title: Expression of cyclooxygenase-2 is regulated by glycogen synthase kinase-3beta in gastric cancer cells.

Journal: The Journal of biological chemistry 20060224

Title: Pharmacologic modulation of glycogen synthase kinase-3beta promotes p53-dependent apoptosis through a direct Bax-mediated mitochondrial pathway in colorectal cancer cells.

Journal: Cancer research 20051001

Title: GSK-3beta inhibitors attenuate the organ injury/dysfunction caused by endotoxemia in the rat.

Journal: Critical care medicine 20050901

Title: GSK-3beta reactivation with LY294002 sensitizes hepatoma cells to chemotherapy-induced apoptosis.

Journal: International journal of oncology 20050701

Title: Inhibition of GSK3beta is a common event in neuroprotection by different survival factors.

Journal: Brain research. Molecular brain research 20050613

Title: Glycogen synthase kinase 3 activity mediates neuronal pentraxin 1 expression and cell death induced by potassium deprivation in cerebellar granule cells.

Journal: Molecular pharmacology 20050401

Title: Constitutive activation of GSK3 down-regulates glycogen synthase abundance and glycogen deposition in rat skeletal muscle cells.

Journal: The Journal of biological chemistry 20050311

Title: Role of glycogen synthase kinase 3beta in rapamycin-mediated cell cycle regulation and chemosensitivity.

Journal: Cancer research 20050301

Title: Implication of cyclin-dependent kinase 5 in the neuroprotective properties of lithium.

Journal: Neuroscience 20050101

Title: Examining the correlations between GSK-3 inhibitory properties and anti-convulsant efficacy of valproate and valproate-related compounds.

Journal: Bioorganic & medicinal chemistry letters 20041115

Title: GSK-3beta inhibition by lithium confers resistance to chemotherapy-induced apoptosis through the repression of CD95 (Fas/APO-1) expression.

Journal: Experimental cell research 20041101

Title: Inhibition of glycogen synthase kinase-3 represses androgen receptor activity and prostate cancer cell growth.

Journal: Oncogene 20041014

Title: Opioid-induced cardioprotection occurs via glycogen synthase kinase beta inhibition during reperfusion in intact rat hearts.

Journal: Circulation research 20040416

Title: Glycogen synthase kinase-3 regulates cytoskeleton and translocation of Rac1 in long cellular extensions of human keratinocytes.

Journal: Experimental cell research 20040201

Title: Glycogen synthase kinase-3 regulates formation of long lamellipodia in human keratinocytes.

Journal: Journal of cell science 20030915

Title: Use of lithium and SB-415286 to explore the role of glycogen synthase kinase-3 in the regulation of glucose transport and glycogen synthase.

Journal: European journal of biochemistry 20030901

Title: Glycogen synthase kinase-3 inhibitors protect central neurons against excitotoxicity.

Journal: Neuroreport 20030806

Title: PI3-kinase-induced hyperreactivity in DOCA-salt hypertension is independent of GSK-3 activity.

Journal: Hypertension (Dallas, Tex. : 1979) 20030401

Title: Evidence that the dephosphorylation of Ser(535) in the epsilon-subunit of eukaryotic initiation factor (eIF) 2B is insufficient for the activation of eIF2B by insulin.

Journal: The Biochemical journal 20021015

Title: Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

Journal: The Journal of biological chemistry 20020419

Title: GSK-3 inhibition by adenoviral FRAT1 overexpression is neuroprotective and induces Tau dephosphorylation and beta-catenin stabilisation without elevation of glycogen synthase activity.

Journal: FEBS letters 20011102

Title: Inhibition of GSK-3 selectively reduces glucose-6-phosphatase and phosphatase and phosphoenolypyruvate carboxykinase gene expression.

Journal: Diabetes 20010501

Title: Selective small-molecule inhibitors of glycogen synthase kinase-3 activity protect primary neurones from death.

Journal: Journal of neurochemistry 20010401

Title: 3-Anilino-4-arylmaleimides: potent and selective inhibitors of glycogen synthase kinase-3 (GSK-3).

Journal: Bioorganic & medicinal chemistry letters 20010312

Title: Selective small molecule inhibitors of glycogen synthase kinase-3 modulate glycogen metabolism and gene transcription.

Journal: Chemistry & biology 20001001

Title: Potential role of glycogen synthase kinase-3 in skeletal muscle insulin resistance of type 2 diabetes.

Journal: Diabetes 20000201

Title: Increased glycogen synthase kinase-3 activity in diabetes- and obesity-prone C57BL/6J mice.

Journal: Diabetes 19990801

Title: Tau protein kinase I is essential for amyloid beta-protein-induced neurotoxicity.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19930815

Title: Coghlan MP, et al. Selective small molecule inhibitors of glycogen synthase kinase-3 modulate glycogen metabolism and gene transcription. Chem Biol. 2000 Oct;7(10):793-803.

Title: Pizarro JG, et al. Neuroprotective effects of SB-415286 on hydrogen peroxide-induced cell death in B65 rat neuroblastoma cells and neurons. Int J Dev Neurosci. 2008 May-Jun;26(3-4):269-76.

Title: MacAulay K, et al. Use of lithium and SB-415286 to explore the role of glycogen synthase kinase-3 in the regulation of glucose transport and glycogen synthase. Eur J Biochem. 2003 Sep;270(18):3829-38.

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Tags:264218-23-7 Molecular Formula|264218-23-7 MDL|264218-23-7 SMILES|264218-23-7 1H-Pyrrole-2,5-dione, 3-[(3-chloro-4-hydroxyphenyl)amino]-4-(2-nitrophenyl)-