Details
Stereochemistry | RACEMIC |
Molecular Formula | C20H16N6S |
Molecular Weight | 372.4481 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
c1ccc2c(c1)nc(C(C#N)c3cc[nH]c(=NCCc4cccnc4)n3)s2
InChI
InChIKey=RCYPVQCPYKNSTG-UHFFFAOYSA-N
InChI=1S/C20H16N6S/c21-12-15(19-25-17-5-1-2-6-18(17)27-19)16-8-11-24-20(26-16)23-10-7-14-4-3-9-22-13-14/h1-6,8-9,11,13,15H,7,10H2,(H,23,24,26)
Molecular Formula | C20H16N6S |
Molecular Weight | 372.4481 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/14988419https://www.ncbi.nlm.nih.gov/pubmed/14988419 | https://www.ncbi.nlm.nih.gov/pubmed/15999997Curator's Comment:: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/15210584 | https://www.ncbi.nlm.nih.gov/pubmed/15715656 | https://www.ncbi.nlm.nih.gov/pubmed/19947601 | https://www.ncbi.nlm.nih.gov/pubmed/16972261
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14988419https://www.ncbi.nlm.nih.gov/pubmed/14988419 | https://www.ncbi.nlm.nih.gov/pubmed/15999997
Curator's Comment:: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/15210584 | https://www.ncbi.nlm.nih.gov/pubmed/15715656 | https://www.ncbi.nlm.nih.gov/pubmed/19947601 | https://www.ncbi.nlm.nih.gov/pubmed/16972261
AS601245 is a JNK inhibitor which was shown to have neuroprotective properties in vivo. AS601245 was tested on rat model of cerebral ischemia and demonstrated good potency.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19947601
Curator's Comment:: Known to be CNS active in Gerbils. Human data not available.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2276 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14988419 |
0.15 µM [IC50] | ||
Target ID: CHEMBL4179 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14988419 |
0.22 µM [IC50] | ||
Target ID: CHEMBL2637 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14988419 |
0.07 µM [IC50] | ||
Target ID: P53779 Gene ID: 5602.0 Gene Symbol: MAPK10 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14988419 |
70.0 nM [IC50] | ||
Target ID: P45983|||Q308M2 Gene ID: 5599.0 Gene Symbol: MAPK8 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14988419 |
150.0 nM [IC50] | ||
Target ID: P80192 Gene ID: 4293.0 Gene Symbol: MAP3K9 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14988419 |
220.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
AS601245 (1,3-benzothiazol-2-yl (2-[[2-(3-pyridinyl) ethyl] amino]-4 pyrimidinyl) acetonitrile): a c-Jun NH2-terminal protein kinase inhibitor with neuroprotective properties. | 2004 Jul |
|
Inhibition of c-Jun N-terminal kinase decreases cardiomyocyte apoptosis and infarct size after myocardial ischemia and reperfusion in anaesthetized rats. | 2004 Jul |
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Control of death receptor and mitochondrial-dependent apoptosis by c-Jun N-terminal kinase in hippocampal CA1 neurones following global transient ischaemia. | 2005 Mar |
|
AS601245, a c-Jun NH2-terminal kinase (JNK) inhibitor, reduces axon/dendrite damage and cognitive deficits after global cerebral ischaemia in gerbils. | 2008 Jan |
|
Rosiglitazone and AS601245 decrease cell adhesion and migration through modulation of specific gene expression in human colon cancer cells. | 2012 |
|
AS601245, an Anti-Inflammatory JNK Inhibitor, and Clofibrate Have a Synergistic Effect in Inducing Cell Responses and in Affecting the Gene Expression Profile in CaCo-2 Colon Cancer Cells. | 2012 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14988419
Gerbils were treated with AS601245 40, 60, and 80 mg/kg administered as pretreatment (1 h before and 24 h after 5 min of ischemia) or post-treatment (15 min and 24 h after 5 min of ischemia).
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16972261
The human leukemia cell lines U-937 (promonocytic) and NB4 (acute promyelocytic), and Bcl-2-transfected U-937 cells, were routinely grown in RPMI 1640 supplemented with 10% (v/v) heat-inactivated calf serum, 0.2% sodium bicarbonate and antibiotics in a humidified 5% CO2 atmosphere at 37C. For experiments, 16–24 h before the initiation of the treatments the cell concentration was adjusted at 10^5 cells/ml. Stock solutions of PD98059 (20 mM), AS601245 (20 mM), LY294002 (20 mM), were prepared in dimethyl sulfoxide. All these solutions were stored at -20C. Cells were treated with 2.5mkM of AS601245 for 24h.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 04:22:38 UTC 2021
by
admin
on
Sat Jun 26 04:22:38 UTC 2021
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Record UNII |
Y9A2N9O85G
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Record Status |
Validated (UNII)
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Record Version |
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861411-83-8
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Y9A2N9O85G
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345987-15-7
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10109823
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