6-(4-{[4-(2H5)ethylpiperazin-1-yl]methyl}phenyl)-N-[(1R)-1-phenylethyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

• ChemBase ID: 159580
• Molecular Formular: C27H32N6
• Molecular Mass: 440.58318
• Monoisotopic Mass: 440.26884505
• SMILES: c1nc(c2c(n1)[nH]c(c2)c1ccc(cc1)CN1CCN(CC1)CC)N[C@@H](c1ccccc1)C
• Canonical SMILES: CCN1CCN(CC1)Cc1ccc(cc1)c1cc2c([nH]1)ncnc2N[C@@H](c1ccccc1)C
• InChI: InChI=1S/C27H32N6/c1-3-32-13-15-33(16-14-32)18-21-9-11-23(12-10-21)25-17-24-26(28-19-29-27(24)31-25)30-20(2)22-7-5-4-6-8-22/h4-12,17,19-20H,3,13-16,18H2,1-2H3,(H2,28,29,30,31)/t20-/m1/s1
• InChIKey: OONFNUWBHFSNBT-HXUWFJFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(4-{[4-(^2H₅)ethylpiperazin-1-yl]methyl}phenyl)-N-[(1R)-1-phenylethyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine
• IUPAC Traditional name: 6-(4-{[4-(^2H₅)ethylpiperazin-1-yl]methyl}phenyl)-N-[(1R)-1-phenylethyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine
• Synonyms: 6-[4-[(4-(Ethyl-d5)-1-piperazinyl)methyl]phenyl]-N-[(1R)-1-phenylethyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine; [6-[4-[(4-(Ethyl-d5)piperazin-1-yl)methyl]phenyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-((R)-1-phenylethyl)amine; NVP-AEE 788-d5; AEE 788-d5

Database IDs

• PubChem SID: 162253715
• PubChem CID: 71313049

CALCULATED PROPERTIES

• Acid pKa: 12.385738
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.05446807
• LogD (pH = 7.4): 2.9482305
• Log P: 4.4367943
• Molar Refractivity: 137.6552 cm^3
• Polarizability: 53.761948 Å^3
• Polar Surface Area: 60.08 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A325602

Labelled AEE 788. A novel dual receptor tyrosine kinase inhibitor of the EGF and the VEGF receptor, for treatment of human HCC cell lines and in a s.c. xenograft model.

REFERENCES

• Fang, D., et al.: J. Biol. Chem., 282, 11221 (2001)
• Ito, Y., et al.: Br. J. Cancer., 84, 1377 (2001)
• Huether, A., et al.: Biochem. Pharmacol., 70, 1568 (2001)
• Zhu, A., et al.: J. Clin. Oncol. 24, 1898 (2001)