Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C12H12N4O4S |
| Molecular Weight | 308.313 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(CNC(=O)NC2=NC=C(S2)[N+]([O-])=O)C=C1
InChI
InChIKey=YAEMHJKFIIIULI-UHFFFAOYSA-N
InChI=1S/C12H12N4O4S/c1-20-9-4-2-8(3-5-9)6-13-11(17)15-12-14-7-10(21-12)16(18)19/h2-5,7H,6H2,1H3,(H2,13,14,15,17)
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/15315719 | http://adisinsight.springer.com/drugs/800020125Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12928438
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15315719 | http://adisinsight.springer.com/drugs/800020125
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12928438
AstraZeneca was developing the thiazole AR-AO-14418, a selective inhibitor of glycogen synthase kinase 3β (GSK-3β), for the treatment of Alzheimer's disease and major depressive disorder. AR-AO-14418 is an important research tool in as much as, at concentrations that AR-AO-14418 is able to inhibit GSK3 activity, this compound did not affect the activity of other 26 protein kinases tested, and especially does not inhibit cdc2 and cdk5, two GSK3-related kinases that are inhibited by published GSK3 inhibitors. Furthermore, AR-AO-14418 constitutes a lead compound with therapeutic potential for the treatment of AD, as well as other neurodegenerative disorders. Later preclinical studies of AR-AO-14418 were discontinued.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Increased glycogen synthase kinase-3 activity in diabetes- and obesity-prone C57BL/6J mice. | 1999 Aug |
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| Potential role of glycogen synthase kinase-3 in skeletal muscle insulin resistance of type 2 diabetes. | 2000 Feb |
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| Structural insights and biological effects of glycogen synthase kinase 3-specific inhibitor AR-A014418. | 2003 Nov 14 |
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| AR-A014418, a selective GSK-3 inhibitor, produces antidepressant-like effects in the forced swim test. | 2004 Dec |
|
| GSK-3beta inhibition reverses axonal transport defects and behavioural phenotypes in Drosophila. | 2004 May |
|
| Glycogen synthase kinase-3beta participates in nuclear factor kappaB-mediated gene transcription and cell survival in pancreatic cancer cells. | 2005 Mar 15 |
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| The Wnt signaling pathway as a target for the treatment of neurodegenerative disorders. | 2006 Jan |
|
| Antidepressant-like effect of the novel thiadiazolidinone NP031115 in mice. | 2008 Aug 1 |
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| Maintenance of constitutive IkappaB kinase activity by glycogen synthase kinase-3alpha/beta in pancreatic cancer. | 2008 Oct 1 |
|
| Exploring complex protein-ligand recognition mechanisms with coarse metadynamics. | 2009 Apr 9 |
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| Glycogen synthase kinase-3: a new therapeutic target in renal cell carcinoma. | 2009 Dec 15 |
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| Elevated glycogen synthase kinase-3 activity in Fragile X mice: key metabolic regulator with evidence for treatment potential. | 2009 Feb |
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| Potential therapeutic effect of glycogen synthase kinase 3beta inhibition against human glioblastoma. | 2009 Feb 1 |
|
| Inhibition of endothelial progenitor cell glycogen synthase kinase-3beta results in attenuated neointima formation and enhanced re-endothelialization after arterial injury. | 2009 Jul 1 |
|
| Epithelial cell survival by activating transcription factor 3 (ATF3) in response to chemical ribosome-inactivating stress. | 2009 Mar 15 |
|
| Glycogen synthase kinase-3β indirectly facilitates interferon-γ-induced nuclear factor-κB activation and nitric oxide biosynthesis. | 2010 Dec 15 |
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| Neurotoxicity induced by okadaic acid in the human neuroblastoma SH-SY5Y line can be differentially prevented by α7 and β2* nicotinic stimulation. | 2011 Sep |
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| Selectively silencing GSK-3 isoforms reduces plaques and tangles in mouse models of Alzheimer's disease. | 2012 May 23 |
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| Inhibition of GSK-3β reverses the pro-apoptotic effect of proadifen (SKF-525A) in HT-29 colon adenocarcinoma cells. | 2012 Sep |
Patents
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87KSH90Q6D
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448014
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487021-52-3
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DTXSID80332270
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ACTIVE MOIETY
