3-[(3-bromophenyl)methyl]-1-tert-butyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

• ChemBase ID: 159889
• Molecular Formular: C16H18BrN5
• Molecular Mass: 360.25162
• Monoisotopic Mass: 359.0745576
• SMILES: c1nc(c2c(n1)n(nc2Cc1cc(ccc1)Br)C(C)(C)C)N
• Canonical SMILES: Brc1cccc(c1)Cc1nn(c2c1c(N)ncn2)C(C)(C)C
• InChI: InChI=1S/C16H18BrN5/c1-16(2,3)22-15-13(14(18)19-9-20-15)12(21-22)8-10-5-4-6-11(17)7-10/h4-7,9H,8H2,1-3H3,(H2,18,19,20)
• InChIKey: FTICVONBLRGQJW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(3-bromophenyl)methyl]-1-tert-butyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine
• IUPAC Traditional name: 3-[(3-bromophenyl)methyl]-1-tert-butylpyrazolo[3,4-d]pyrimidin-4-amine
• Synonyms: 3-[(3-Bromophenyl)methyl]-1-(1,1-dimethylethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine; 3-BrB-PP1; 4-Amino-1-tert-butyl-3-(3-bromobenzyl)pyrazolo[3,4-d]pyrimidine

Database IDs

• CAS Number: 956025-99-3
• PubChem SID: 162254024
• PubChem CID: 24865027

CALCULATED PROPERTIES

• Acid pKa: 19.982689
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.5090895
• LogD (pH = 7.4): 3.37785
• Log P: 3.4178894
• Molar Refractivity: 103.6617 cm^3
• Polarizability: 34.689983 Å^3
• Polar Surface Area: 69.62 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A602985

4-Amino-1-tert-butyl-3-(3-bromobenzyl)pyrazolo[3,4-d]pyrimidine is a small molecule Akt inhibitor. The kinase Akt is a key signaling node in regulating cellular growth and survival.

REFERENCES

• Eblen, S., et al.: J. Biol. Chem., 278, 14926 (2003)
• Lindsley, C., et al.: Bioorg. Med. Chem. Lett., 15, 761 (2003)
• Manning, B., et al.: Cell, 129, 1261 (2003)
• Heerding, D., et al.: J. Med. Chem., 51, 5663 (2003)