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)
| Molecular Formula | C12H12N4O4S |
| Molecular Weight | 308.313 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Potential role of glycogen synthase kinase-3 in skeletal muscle insulin resistance of type 2 diabetes. | 2000 Feb |
|
| Structural insights and biological effects of glycogen synthase kinase 3-specific inhibitor AR-A014418. | 2003 Nov 14 |
|
| Inhibition of glycogen synthase kinase-3beta protects dopaminergic neurons from MPTP toxicity. | 2007 Jun |
|
| Potential therapeutic effect of glycogen synthase kinase 3beta inhibition against human glioblastoma. | 2009 Feb 1 |
|
| Glycogen synthase kinase-3beta (GSK-3beta) inhibitors AR-A014418 and B6B3O prevent human immunodeficiency virus-mediated neurotoxicity in primary human neurons. | 2009 Sep |
|
| Inhibition of glycogen synthase kinase 3beta (GSK3beta) decreases inflammatory responses in brain endothelial cells. | 2010 Feb |
|
| Comprehensive assay of kinase catalytic activity reveals features of kinase inhibitor selectivity. | 2011 Oct 30 |
|
| Inhibition of GSK-3β reverses the pro-apoptotic effect of proadifen (SKF-525A) in HT-29 colon adenocarcinoma cells. | 2012 Sep |
Patents
Sample Use Guides
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:00:50 GMT 2023
by
admin
on
Sat Dec 16 08:00:50 GMT 2023
|
| Record UNII |
87KSH90Q6D
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Code | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
DB01950
Created by
admin on Sat Dec 16 08:00:50 GMT 2023 , Edited by admin on Sat Dec 16 08:00:50 GMT 2023
|
PRIMARY | |||
|
87KSH90Q6D
Created by
admin on Sat Dec 16 08:00:50 GMT 2023 , Edited by admin on Sat Dec 16 08:00:50 GMT 2023
|
PRIMARY | |||
|
448014
Created by
admin on Sat Dec 16 08:00:50 GMT 2023 , Edited by admin on Sat Dec 16 08:00:50 GMT 2023
|
PRIMARY | |||
|
487021-52-3
Created by
admin on Sat Dec 16 08:00:50 GMT 2023 , Edited by admin on Sat Dec 16 08:00:50 GMT 2023
|
PRIMARY | |||
|
DTXSID80332270
Created by
admin on Sat Dec 16 08:00:50 GMT 2023 , Edited by admin on Sat Dec 16 08:00:50 GMT 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
TARGET -> INHIBITOR |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
