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844499-71-4

844499-71-4 | 4-Hydroxy-3-(2'-hydroxy-1,1'-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

CAS No: 844499-71-4 Catalog No: AG0038EQ MDL No:MFCD11977269

Product Description

Catalog Number:
AG0038EQ
Chemical Name:
4-Hydroxy-3-(2'-hydroxy-1,1'-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile
CAS Number:
844499-71-4
Molecular Formula:
C20H12N2O3S
Molecular Weight:
360.3859
MDL Number:
MFCD11977269
IUPAC Name:
4-hydroxy-3-[4-(2-hydroxyphenyl)phenyl]-6-oxo-7H-thieno[2,3-b]pyridine-5-carbonitrile
InChI:
InChI=1S/C20H12N2O3S/c21-9-14-18(24)17-15(10-26-20(17)22-19(14)25)12-7-5-11(6-8-12)13-3-1-2-4-16(13)23/h1-8,10,23H,(H2,22,24,25)
InChI Key:
CTESJDQKVOEUOY-UHFFFAOYSA-N
SMILES:
N#Cc1c(=O)[nH]c2c(c1O)c(cs2)c1ccc(cc1)c1ccccc1O
UNII:
P68477CD2C

Properties

Complexity:
647  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
360.057g/mol
Formal Charge:
0
Heavy Atom Count:
26  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
360.387g/mol
Monoisotopic Mass:
360.057g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
122A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4.1  

Literature

Title Journal
Effect of A-769662, a direct AMPK activator, on Tlr-4 expression and activity in mice heart tissue. Iranian journal of basic medical sciences 20161201
Activation of AMPK-induced autophagy ameliorates Huntington disease pathology in vitro. Neuropharmacology 20160901
Bavachalcone-induced manganese superoxide dismutase expression through the AMP-activated protein kinase pathway in human endothelial cells. Pharmacology 20150101
Identification of potent Yes1 kinase inhibitors using a library screening approach. Bioorganic & medicinal chemistry letters 20130801
Activation of AMP-activated protein kinase inhibits the proliferation of human endothelial cells. The Journal of pharmacology and experimental therapeutics 20120901
Activation of AMP-activated protein kinase stimulates Na+,K+-ATPase activity in skeletal muscle cells. The Journal of biological chemistry 20120706
The ancient drug salicylate directly activates AMP-activated protein kinase. Science (New York, N.Y.) 20120518
AMP-activated protein kinase phosphorylates and inactivates liver glycogen synthase. The Biochemical journal 20120401
Activation of AMP-activated protein kinase (AMPK) provides a metabolic barrier to reprogramming somatic cells into stem cells. Cell cycle (Georgetown, Tex.) 20120301
Monitoring metabolites consumption and secretion in cultured cells using ultra-performance liquid chromatography quadrupole-time of flight mass spectrometry (UPLC-Q-ToF-MS). Analytical and bioanalytical chemistry 20120101
5-Aminoimidazole-4-carboxyamide-ribonucleoside (AICAR)-stimulated hepatic expression of Cyp4a10, Cyp4a14, Cyp4a31, and other peroxisome proliferator-activated receptor α-responsive mouse genes is AICAR 5'-monophosphate-dependent and AMP-activated protein kinase-independent. The Journal of pharmacology and experimental therapeutics 20111201
A small molecule AMPK activator protects the heart against ischemia-reperfusion injury. Journal of molecular and cellular cardiology 20110701
Genistein, resveratrol, and 5-aminoimidazole-4-carboxamide-1-β-D-ribofuranoside induce cytochrome P450 4F2 expression through an AMP-activated protein kinase-dependent pathway. The Journal of pharmacology and experimental therapeutics 20110401
AMP-activated protein kinase regulates glucagon secretion from mouse pancreatic alpha cells. Diabetologia 20110101
Escherichia coli expression, purification and characterization of functional full-length recombinant alpha2beta2gamma3 heterotrimeric complex of human AMP-activated protein kinase. Protein expression and purification 20101001
Stimulation of human and mouse erythrocyte Na(+)-K(+)-2Cl(-) cotransport by osmotic shrinkage does not involve AMP-activated protein kinase, but is associated with STE20/SPS1-related proline/alanine-rich kinase activation. The Journal of physiology 20100701
AMP-activated protein kinase induces actin cytoskeleton reorganization in epithelial cells. Biochemical and biophysical research communications 20100604
Regulation of Na+-coupled glucose carrier SGLT1 by AMP-activated protein kinase. Molecular membrane biology 20100401
Involvement of mTOR in globular adiponectin-induced generation of reactive oxygen species. Free radical research 20100201
Kinetic evidence for unique regulation of GLUT4 trafficking by insulin and AMP-activated protein kinase activators in L6 myotubes. The Journal of biological chemistry 20100115
AMP-activated protein kinase activator A-769662 is an inhibitor of the Na(+)-K(+)-ATPase. American journal of physiology. Cell physiology 20091201
A-769662 activates AMPK beta1-containing complexes but induces glucose uptake through a PI3-kinase-dependent pathway in mouse skeletal muscle. American journal of physiology. Cell physiology 20091001
Inhibitory effects of A-769662, a novel activator of AMP-activated protein kinase, on 3T3-L1 adipogenesis. Biological & pharmaceutical bulletin 20090601
AMP-activated protein kinase inhibits alkaline pH- and PKA-induced apical vacuolar H+-ATPase accumulation in epididymal clear cells. American journal of physiology. Cell physiology 20090401
Role of adenosine 5'-monophosphate-activated protein kinase in interleukin-6 release from isolated mouse skeletal muscle. Endocrinology 20090201
Beyond AICA riboside: in search of new specific AMP-activated protein kinase activators. IUBMB life 20090101
Thienopyridone drugs are selective activators of AMP-activated protein kinase beta1-containing complexes. Chemistry & biology 20081124
Defining the mechanism of activation of AMP-activated protein kinase by the small molecule A-769662, a member of the thienopyridone family. The Journal of biological chemistry 20071109
Mechanism of action of A-769662, a valuable tool for activation of AMP-activated protein kinase. The Journal of biological chemistry 20071109
Identification and characterization of a small molecule AMPK activator that treats key components of type 2 diabetes and the metabolic syndrome. Cell metabolism 20060601

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