N-methyl-N-{2-[({2-[(2-oxo-2,3-dihydro-1H-indol-5-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl}amino)methyl]phenyl}methanesulfonamide

• ChemBase ID: 176249
• Molecular Formular: C22H21F3N6O3S
• Molecular Mass: 506.5007496
• Monoisotopic Mass: 506.13479422
• SMILES: c1c(c(nc(n1)Nc1ccc2c(c1)CC(=O)N2)NCc1ccccc1N(S(=O)(=O)C)C)C(F)(F)F
• Canonical SMILES: O=C1Nc2c(C1)cc(cc2)Nc1ncc(c(n1)NCc1ccccc1N(S(=O)(=O)C)C)C(F)(F)F
• InChI: InChI=1S/C22H21F3N6O3S/c1-31(35(2,33)34)18-6-4-3-5-13(18)11-26-20-16(22(23,24)25)12-27-21(30-20)28-15-7-8-17-14(9-15)10-19(32)29-17/h3-9,12H,10-11H2,1-2H3,(H,29,32)(H2,26,27,28,30)
• InChIKey: POJZIZBONPAWIV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-methyl-N-{2-[({2-[(2-oxo-2,3-dihydro-1H-indol-5-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl}amino)methyl]phenyl}methanesulfonamide
• IUPAC Traditional name: N-methyl-N-{2-[({2-[(2-oxo-1,3-dihydroindol-5-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl}amino)methyl]phenyl}methanesulfonamide
• Synonyms: N-[2-[[[2-[(2,3-Dihydro-2-oxo-1H-indol-5-yl)amino]-5-(trifluoromethyl)-4-pyrimidinyl]amino]methyl]phenyl]-N-methylmethanesulfonamide; N-Methyl-N-[2-[[[2-[(2-oxo-2,3-dihydro-1H-indol-5-yl)amino]-5-trifluoromethylpyrimidin-4-yl]amino]methyl]phenyl]methanesulfonamide; PF 431396; PF 431396

Database IDs

• CAS Number: 717906-29-1
• PubChem SID: 164232159
• PubChem CID: 11598628

CALCULATED PROPERTIES

• Acid pKa: 13.114567
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 2.4475973
• LogD (pH = 7.4): 2.5324183
• Log P: 2.5336242
• Molar Refractivity: 127.3549 cm^3
• Polarizability: 46.170143 Å^3
• Polar Surface Area: 116.32 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P218290

PF 431396 is a dual focal adhesion kinase (FAK) and proline-rich tyrosine kinase 2 (PYK2) inhibitor (IC50 values are 2 and 11 nM respectively). Promotes osteoblast recruitment and activity, and stimulates bone formation in ovariectomized rats.

REFERENCES

• Han, et al.: J. Biol. Chem., 284 13193 (2009)
• Allen, et al.: J. Med. Chem., 53 4332 (2009)