6-[(4-{[(3-methanesulfonylphenyl)methyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl)amino]-1,2,3,4-tetrahydroquinolin-2-one

• ChemBase ID: 154608
• Molecular Formular: C22H20F3N5O3S
• Molecular Mass: 491.4861096
• Monoisotopic Mass: 491.12389519
• SMILES: CS(=O)(=O)c1cccc(c1)CNc1c(cnc(n1)Nc1ccc2c(c1)CCC(=O)N2)C(F)(F)F
• Canonical SMILES: O=C1CCc2c(N1)ccc(c2)Nc1ncc(c(n1)NCc1cccc(c1)S(=O)(=O)C)C(F)(F)F
• InChI: InChI=1S/C22H20F3N5O3S/c1-34(32,33)16-4-2-3-13(9-16)11-26-20-17(22(23,24)25)12-27-21(30-20)28-15-6-7-18-14(10-15)5-8-19(31)29-18/h2-4,6-7,9-10,12H,5,8,11H2,1H3,(H,29,31)(H2,26,27,28,30)
• InChIKey: HESLKTSGTIBHJU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-[(4-{[(3-methanesulfonylphenyl)methyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl)amino]-1,2,3,4-tetrahydroquinolin-2-one
• IUPAC Traditional name: 6-[(4-{[(3-methanesulfonylphenyl)methyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl)amino]-3,4-dihydro-1H-quinolin-2-one
• Synonyms: 3,4-Dihydro-6-[[4-[[[3-(methylsulfonyl)phenyl]methyl]amino]-5-(trifluoromethyl)-2-pyrimidinyl]amino]-2(1H)-quinolinone; 6-[(4-((3-(Methanesulfonyl)benzyl)amino)-5-trifluoromethylpyrimidin-2-yl)amino]-3,4-dihydro-1H-quinolin-2-one; PF 573228; PF-573228; 6-[4-(3-Methanesulfonyl-benzylamino)-5-trifluoromethyl-pyrimidin-2-ylamino]-3,4-dihydro-1H-quinolin-2-one; PF-228; PF-573228; PF 573228

Database IDs

• CAS Number: 869288-64-2
• MDL Number: MFCD11519967
• PubChem SID: 162248746
• PubChem CID: 11612883

CALCULATED PROPERTIES

• Acid pKa: 13.338437
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 3.135544
• LogD (pH = 7.4): 3.2204788
• Log P: 3.2216861
• Molar Refractivity: 124.3796 cm^3
• Polarizability: 44.976562 Å^3
• Polar Surface Area: 113.08 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: white to off-white powder

Safety Information

• Storage Condition: Refrigerator
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-36
• Safety Statements: 26-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H319
• GHS Precautionary statements: P301 + P310-P305 + P351 + P338
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: FAK

Product Information

• Purity: ≥95% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C22H20F3N5O3S

DETAILS

Sigma Aldrich - PZ0117

Biochem/physiol Actions
PF-573228 is a focal adhesion kinase (FAK) inhibitor; Non-receptor tyrosine kinase inhibitor.
Legal Information
Sold for research purposes under agreement from Pfizer Inc.

Toronto Research Chemicals - P293950

A novel focal adhesion kinase inhibitor that has been shown to suppress the adverse phenotype of endocrine-resistant breast cancer cells and improve endocrine response in endocrine-sensitive cells.

REFERENCES

• Slack-Davis, J.K. et al.: J. Biol. Chem., 282, 14845 (2007)
• Hiscox, S. et al.: Breast Cancer Res. Treat., 125, 659 (2007)