3-(3-chlorophenoxymethyl)-1-(oxan-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine hydrochloride

• ChemBase ID: 176422
• Molecular Formular: C17H19Cl2N5O2
• Molecular Mass: 396.27106
• Monoisotopic Mass: 395.09158023
• SMILES: c1nc(c2c(n1)n(nc2COc1cccc(c1)Cl)C1CCOCC1)N.Cl
• Canonical SMILES: Clc1cccc(c1)OCc1nn(c2c1c(N)ncn2)C1CCOCC1.Cl
• InChI: InChI=1S/C17H18ClN5O2.ClH/c18-11-2-1-3-13(8-11)25-9-14-15-16(19)20-10-21-17(15)23(22-14)12-4-6-24-7-5-12;/h1-3,8,10,12H,4-7,9H2,(H2,19,20,21);1H
• InChIKey: QZXZQMUZEHTFHD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(3-chlorophenoxymethyl)-1-(oxan-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine hydrochloride
• IUPAC Traditional name: 3-(3-chlorophenoxymethyl)-1-(oxan-4-yl)pyrazolo[3,4-d]pyrimidin-4-amine hydrochloride
• Synonyms: 3-[(3-Chlorophenoxy)methyl]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine Hydrochloride; PF 4800567 Hydrochloride; PF-4800567 Hydrochloride

Database IDs

• PubChem SID: 164232332
• PubChem CID: 71751553

CALCULATED PROPERTIES

• Acid pKa: 19.766527
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 1.0145266
• LogD (pH = 7.4): 1.81084
• Log P: 1.8429716
• Molar Refractivity: 106.7538 cm^3
• Polarizability: 36.432877 Å^3
• Polar Surface Area: 88.08 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P294035

PF 4800567 is a selective casein kinase 1ε inhibitor; displays 22-fold greater potency towards CK1ε than CK1δ (IC50 values are 32 and 711 nM for CK1ε and CK1δ respectively). ATP competitive. Displays minimal effect on the circadian clock.

REFERENCES

• Behrend, L., et al.: Oncogene, 19, 5303 (2000)
• Badura, L., et al.: J. Pharmacol. Exp. Ther., 322, 730 (2000)
• Arora, S., et al.: Cancer Res., 69, 1910 (2000)
• Walton, et al.: J. Pharmacol. Exp. Ther., 330, 430 (2000)