6-[5-(aminomethyl)furan-2-yl]-N-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}quinazolin-4-amine

• ChemBase ID: 165813
• Molecular Formular: C26H20ClFN4O2
• Molecular Mass: 474.9140032
• Monoisotopic Mass: 474.1258818
• SMILES: c1c(cc2c(c1)ncnc2Nc1ccc(c(c1)Cl)OCc1cccc(c1)F)c1oc(cc1)CN
• Canonical SMILES: NCc1ccc(o1)c1ccc2c(c1)c(ncn2)Nc1ccc(c(c1)Cl)OCc1cccc(c1)F
• InChI: InChI=1S/C26H20ClFN4O2/c27-22-12-19(5-8-25(22)33-14-16-2-1-3-18(28)10-16)32-26-21-11-17(4-7-23(21)30-15-31-26)24-9-6-20(13-29)34-24/h1-12,15H,13-14,29H2,(H,30,31,32)
• InChIKey: NQHFMDSFFGTFSK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-[5-(aminomethyl)furan-2-yl]-N-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}quinazolin-4-amine
• IUPAC Traditional name: 6-[5-(aminomethyl)furan-2-yl]-N-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}quinazolin-4-amine
• Synonyms: 6-[5-(Aminomethyl)-2-furanyl]-N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-4-quinazolinamine; [6-(5-Aminomethylfuran-2-yl)quinazolin-4-yl][3-chloro-4-(3-fluorobenzyloxy)phenyl]amine; N-De[2-(methylsulfonyl)ethyl] Lapatinib

Database IDs

• CAS Number: 697299-82-4
• PubChem SID: 162259946
• PubChem CID: 21952026

CALCULATED PROPERTIES

• Acid pKa: 15.986492
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.0724752
• LogD (pH = 7.4): 4.770967
• Log P: 5.526236
• Molar Refractivity: 129.5752 cm^3
• Polarizability: 51.599712 Å^3
• Polar Surface Area: 86.2 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D231270

A reactive metabolite of Lapatinib (L175800) which is associated with various drug toxicities. Lapatinib is metabolized mainly by P450 3A4 to form O- and N-dealkylated metabolites.

REFERENCES

• He, K., et al.: Chem. Res. Toxicol., 11, 252 (1998)
• Rusnuk, D., et al.: Cancer Res., 61, 7196 (1998)
• Li, X., et al.: Drug Metab. Dispos., 37, 1242 (1998)