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

• ChemBase ID: 159893
• Molecular Formular: C20H21N5
• Molecular Mass: 331.41424
• Monoisotopic Mass: 331.1796957
• SMILES: c1nc(c2c(n1)n(nc2Cc1cccc2c1cccc2)C(C)(C)C)N
• Canonical SMILES: Nc1ncnc2c1c(Cc1cccc3c1cccc3)nn2C(C)(C)C
• InChI: InChI=1S/C20H21N5/c1-20(2,3)25-19-17(18(21)22-12-23-19)16(24-25)11-14-9-6-8-13-7-4-5-10-15(13)14/h4-10,12H,11H2,1-3H3,(H2,21,22,23)
• InChIKey: GDQXJQSQYMMKRA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-tert-butyl-3-(naphthalen-1-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
• IUPAC Traditional name: 1-tert-butyl-3-(naphthalen-1-ylmethyl)pyrazolo[3,4-d]pyrimidin-4-amine
• Synonyms: 1-(1,1-Dimethylethyl)-3-(1-naphthalenylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine; 1-NM-PP1; 4-Amino-1-tert-butyl-3-(1'-naphthylmethyl)pyrazolo[3,4-d]pyrimidine

Database IDs

• CAS Number: 221244-14-0
• PubChem SID: 162254028
• PubChem CID: 5154691

CALCULATED PROPERTIES

• Acid pKa: 19.982422
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.7303116
• LogD (pH = 7.4): 3.5986283
• Log P: 3.6386135
• Molar Refractivity: 112.4891 cm^3
• Polarizability: 39.533142 Å^3
• Polar Surface Area: 69.62 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 175-176°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A603003

A highly potent (IC50=4.3 nM) and uniquely specific tyrosine kinase inhibitor of a rationally engineered v-Src tyrosine kinase.

REFERENCES

• Bishop, A.C., et al.: J. Am. Chem. Soc., 121, 627 (1999)
• Davies, S., et al.: Biochem. J., 351, 95 (1999)
• Regan, J., et al.: J. Med. Chem., 45, 2994 (1999)
• Bain, J., et al.: Biochem. J., 371, 199 (1999)
• Kuma, Y., et al.: J. Biol. Chem., 280, 19472 (200