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1174046-72-0 molecular structure
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N-{4-[(2-amino-3-chloropyridin-4-yl)oxy]-3-fluorophenyl}-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxamide

ChemBase ID: 72894
Molecular Formular: C23H15ClF2N4O3
Molecular Mass: 468.8400064
Monoisotopic Mass: 468.08007448
SMILES and InChIs

SMILES:
n1c(c(c(cc1)Oc1ccc(cc1F)NC(=O)c1c[nH]cc(c1=O)c1ccc(cc1)F)Cl)N
Canonical SMILES:
Fc1ccc(cc1)c1c[nH]cc(c1=O)C(=O)Nc1ccc(c(c1)F)Oc1ccnc(c1Cl)N
InChI:
InChI=1S/C23H15ClF2N4O3/c24-20-19(7-8-29-22(20)27)33-18-6-5-14(9-17(18)26)30-23(32)16-11-28-10-15(21(16)31)12-1-3-13(25)4-2-12/h1-11H,(H2,27,29)(H,28,31)(H,30,32)
InChIKey:
PDYXPCKITKHFOZ-UHFFFAOYSA-N

Cite this record

CBID:72894 http://www.chembase.cn/molecule-72894.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-{4-[(2-amino-3-chloropyridin-4-yl)oxy]-3-fluorophenyl}-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxamide
IUPAC Traditional name
N-{4-[(2-amino-3-chloropyridin-4-yl)oxy]-3-fluorophenyl}-5-(4-fluorophenyl)-4-oxo-1H-pyridine-3-carboxamide
Synonyms
BMS794833
BMS 794833
CAS Number
1174046-72-0
PubChem SID
162037814
PubChem CID
44155856

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Selleck Chemicals
S2201 external link Add to cart Please log in.
Data Source Data ID
PubChem 44155856 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 7.5738134  H Acceptors
H Donor LogD (pH = 5.5) 3.3428543 
LogD (pH = 7.4) 3.6726472  Log P 3.7644732 
Molar Refractivity 120.7555 cm3 Polarizability 44.158302 Å3
Polar Surface Area 106.34 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Storage Condition
-20°C expand Show data source
Target
c-Met expand Show data source
VEGFR expand Show data source
Salt Data
Free Base expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals
Selleck Chemicals - S2201 external link
Research Area
Description Cancer
Biological Activity
Description BMS794833 is a potent ATP competitive inhibitor of Met and VEGFR2 with IC50 of 1.7 nM and 15 nM, respectively.
Targets Met VEGFR2
IC50 1.7 nM 15 nM [1]
In Vitro BMS794833 also inhibits Met receptor activated gastric carcinoma cell line, GTL-16, with IC50 of 39 nM. [1]
In Vivo In GTL-16 human gastric tumor xenografts model, BMS798433 shows greater than 50% TGI for at least one tumor doubling time with no overt toxicity observed during 14 days. BMS798433 also shows complete tumor stasis at a dose of 25 mg/kg against U87 glioblastoma model. [1]
Clinical Trials BMS798433 is currently in Phase I clinical trial against advanced or metastatic solid tumor.
Features
Protocol
Kinase Assay [1]
Met kinase assay BMS798433 is dissolved in DMSO and diluted by water before use. The reaction solution contains baculovirus expressed GST-Met kinase, 20 mM Tris-HCl (pH 7.4), 1 mM MnCl2, 1 mM DTT, 0.1mg BSA, 0.1 mg polyGlu4/tyr, 1μM ATP and 0.2μCi γ–ATP. Reactions are incubated at 30 °C for 1 hour and stopped by 8% TCA. TCA precipitates are collected onto GF/C plates using a universal harvester and the filters are quantitated using liquid scintillation counter.
VEGFR2 assay BMS798433 is dissolved in DMSO and diluted by water before use. The reaction solution contains 20 mM Tris-HCl (pH 7.4), 1 mM MnCl2, 1 mM DTT, 0.1mg BSA, 75 μg polyGlu4/tyr, 1μM ATP, 0.5 μCi γ–ATP and 7.5 ng/rxn enzyme stock (10% glycerol). The reaction is initiated by addition of enzyme and stopped by 30% TCA after 1 hour. Assays are prepared in 96 well plates and incubated at 27 °C for 1 hour. Then acid precipitated with TCA for 20 minutes on ice. Those precipitates are transferred to GF/C plates using a harvester and the filters are quantitated using liquid scintillation counter.
Cell Assay [1]
Cell Lines GTL-16 cells
Concentrations ~ 1 μM
Incubation Time 72 hours
Methods GTL-16 cells are seeded into 96 well plates and incubated for 24 hours. BMS798433 is dissolved in DMSO at 10 mM and diluted with culture medium before use. Then BMS798433 is added to the cells for 72 hours. After that, MTS assay is used to measure the IC50.
Animal Study [1]
Animal Models GTL-16 and U87 xenografts
Formulation
Doses 25 mg/kg
Administration Orally once daily
References
[1] WO2009094417A1

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