4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline-3-carbonitrile

• ChemBase ID: 162701
• Molecular Formular: C26H29Cl2N5O3
• Molecular Mass: 530.44616
• Monoisotopic Mass: 529.16474517
• SMILES: c1(c(cc2c(c1)ncc(c2Nc1cc(c(cc1Cl)Cl)OC)C#N)OC)OCCCN1CCN(CC1)C
• Canonical SMILES: COc1cc2c(cc1OCCCN1CCN(CC1)C)ncc(c2Nc1cc(OC)c(cc1Cl)Cl)C#N
• InChI: InChI=1S/C26H29Cl2N5O3/c1-32-6-8-33(9-7-32)5-4-10-36-25-13-21-18(11-24(25)35-3)26(17(15-29)16-30-21)31-22-14-23(34-2)20(28)12-19(22)27/h11-14,16H,4-10H2,1-3H3,(H,30,31)
• InChIKey: UBPYILGKFZZVDX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline-3-carbonitrile
• IUPAC Traditional name: bosutinib
• Synonyms: 4-[(2,4-Dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]-3-quinolinecarbonitrile; SKI 606; Bosutinib

Database IDs

• CAS Number: 380843-75-4
• PubChem SID: 162256836
• PubChem CID: 5328940

CALCULATED PROPERTIES

• Acid pKa: 15.477387
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 1.2418306
• LogD (pH = 7.4): 3.021281
• Log P: 4.087722
• Molar Refractivity: 142.1209 cm^3
• Polarizability: 56.017532 Å^3
• Polar Surface Area: 82.88 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 131-134°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B676095

A novel Src kinase inhibitor, suppresses migration and invasion of human breast cancer cells.

REFERENCES

• Bjorge, J., et al.: J. Biol. Chem., 275, 41439 (2000)
• Frame, M., et al.: Biochim. Biophys. Acta, 1602, 114 (2000)
• Frame, M., et al.: J. Cell Sci., 117, 989 (2000)
• Ishizawar, R., et al.: Cancer Cell, 6, 209 (2000)
• Diaz, N., et al.: Clin. Cancer Res., 1