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717907-75-0 molecular structure
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N-methyl-N-{3-[({2-[(2-oxo-2,3-dihydro-1H-indol-5-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl}amino)methyl]pyridin-2-yl}methanesulfonamide

ChemBase ID: 73137
Molecular Formular: C21H20F3N7O3S
Molecular Mass: 507.4888096
Monoisotopic Mass: 507.1300432
SMILES and InChIs

SMILES:
c1nc(c(cc1)CNc1c(cnc(n1)Nc1ccc2c(c1)CC(=O)N2)C(F)(F)F)N(C)S(=O)(=O)C
Canonical SMILES:
O=C1Nc2c(C1)cc(cc2)Nc1ncc(c(n1)NCc1cccnc1N(S(=O)(=O)C)C)C(F)(F)F
InChI:
InChI=1S/C21H20F3N7O3S/c1-31(35(2,33)34)19-12(4-3-7-25-19)10-26-18-15(21(22,23)24)11-27-20(30-18)28-14-5-6-16-13(8-14)9-17(32)29-16/h3-8,11H,9-10H2,1-2H3,(H,29,32)(H2,26,27,28,30)
InChIKey:
MZDKLVOWGIOKTN-UHFFFAOYSA-N

Cite this record

CBID:73137 http://www.chembase.cn/molecule-73137.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-methyl-N-{3-[({2-[(2-oxo-2,3-dihydro-1H-indol-5-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl}amino)methyl]pyridin-2-yl}methanesulfonamide
IUPAC Traditional name
N-methyl-N-{3-[({2-[(2-oxo-1,3-dihydroindol-5-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl}amino)methyl]pyridin-2-yl}methanesulfonamide
Synonyms
PF-00562271
PF-562271
CAS Number
717907-75-0
PubChem SID
162038057
PubChem CID
11713159

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 11713159 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 13.114496  H Acceptors
H Donor LogD (pH = 5.5) 1.8244756 
LogD (pH = 7.4) 1.9092047  Log P 1.9104092 
Molar Refractivity 125.5115 cm3 Polarizability 45.3465 Å3
Polar Surface Area 129.21 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

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

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals
Selleck Chemicals - S2672 external link
Research Area
Description Cancer
Biological Activity
Description PF-562271 is a potent, ATP-competitive, reversible inhibitor of FAK and Pyk2 with IC50 of 1.5 nM and 14 nM, respectively.
Targets FAK Pyk2
IC50 1.5 nM 14 nM [1]
In Vitro PF-562271 shows the selective inhibitory effects on FAK and Pyk2 tyrosine kinase activity with IC50 of 1.5 nM and 14 nM, respectively. And in cell-based assays, the IC50 of PF-562271 is shown to be 5 nM for FAK, which is more selective compared to other kinase targets. [1] In 2 dimensional (2D) cultures, PF-562271 results in a dose-dependent cell proliferation inhibition in FAK WT, FAK?/? and FAK kinase-deficient (KD) cells with IC50 of 3.3 μM, 2.08 μM and 2.01 μM, respectively. [2]
In Vivo In several human s.c. xenograft models, PF-562271 exhibits dose-dependent tumor growth inhibition, and produces maximum tumor inhibition for PC-3M, BT474, BxPc3, and LoVo ranging from 78% to 94% inhibition at doses of 25 to 50 mg/kg twice daily, without weight loss, morbidity, or death. [1] PF-562271 (25 mg/kg by p.o.) leads to a significant decrease in tumor progression in both subcutaneous and bone metastasis PC3M-luc-C6 xenograft models. [3] In a Huh7.5 hepatocellular carcinoma xenograft model, combination therapy of sunitinib and PF-562271 targets angiogenesis and tumor aggressiveness, and produces more significant anti-tumor effect than single agent by blocking tumor growth and impacting the ability of the tumor to recover upon withdrawal of the therapy. [4]
Clinical Trials
Features
Protocol
Kinase Assay [1]
Recombinant kinase assay and enzyme kinetics Briefly, purified-activated FAK kinase domain (amino acid 410–689) is reacted with 50 μM ATP and 10 μg per well of a random peptide polymer of Glu and Tyr, p(Glu/Tyr), in kinase buffer [50 mM HEPES (pH 7.5), 125 mM NaCl, and 48 mM MgCl2] for 15 minutes. Phosphorylation of p(Glu/Tyr) is challenged with serially diluted PF-562271 at 1/2-Log concentrations starting at a top concentration of 1 μM. Each concentration is tested in triplicate. Phosphorylation of p(Glu/Tyr) is detected with a general antiphospho-tyrosine (PY20) antibody followed by horseradish peroxidase (HRP)-conjugated goat anti-mouse IgG antibody. HRP substrate is added, and absorbance readings at 450 nm are obtained after addition of stop solution (2 M H2SO4). IC50 values are determined using the Hill-Slope Model. Broad kinase selectivity profiling is performed in house and by using the KinaseProfiler Selectivity Screening Service available through UpState Biotechnology.
Cell Assay [2]
Cell Lines Squamous cell carcinoma (SCC)
Concentrations 0 to 1 μM
Incubation Time 72 hours
Methods Cells are plated for 48 hours before addition of PF-562271. After 3 days cells are fixed by addition of ice cold 25% trichloroacetic acid (TCA) solution prior to staining with Sulforhodamine B (SRB) dye solution. Plates are washed with 1% glacial acetic acid, air-dried and resuspended in 10 mM Tris buffer, pH 10.5 before reading absorbance at 540 nm. Curve fitting and generation of IC50 values is carried out using GraphPad Prism 4 software from six replicates.
Animal Study [1]
Animal Models PC-3M, BT474, BxPc3, LoVo, U87MG, H125 and H460 cells are injected s.c. into the right flank of athymic female mice .
Formulation PF-562271 is dissolved in 5% Gelucire.
Doses ≤100 mg/kg
Administration Administered via p.o.
References
[1] Roberts WG, et al. Cancer Res. 2008, 68(6), 1935-1944.
[2] Serrels A, et al. Int J Cancer. 2012, 131(2), 287-297.
[3] Sun H, et al. Cancer Biol Ther. 2010, 10(1), 38-43.
[4] Bagi CM, et al. Cancer Biol Ther. 2009, 8(9), 856-865.

PATENTS

PATENTS

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INTERNET

INTERNET

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