2-amino-4-{4-chloro-2-[2-(4-fluoro-1H-pyrazol-1-yl)ethoxy]-6-methylphenyl}-N-(2,2-difluoropropyl)-5H,6H,7H-pyrrolo[3,4-d]pyrimidine-6-carboxamide

• ChemBase ID: 176421
• Molecular Formular: C22H23ClF3N7O2
• Molecular Mass: 509.9119296
• Monoisotopic Mass: 509.15538535
• SMILES: c1(nc2c(c(n1)c1c(cc(cc1C)Cl)OCCn1ncc(c1)F)CN(C2)C(=O)NCC(C)(F)F)N
• Canonical SMILES: Nc1nc2CN(Cc2c(n1)c1c(C)cc(cc1OCCn1ncc(c1)F)Cl)C(=O)NCC(F)(F)C
• InChI: InChI=1S/C22H23ClF3N7O2/c1-12-5-13(23)6-17(35-4-3-33-8-14(24)7-29-33)18(12)19-15-9-32(10-16(15)30-20(27)31-19)21(34)28-11-22(2,25)26/h5-8H,3-4,9-11H2,1-2H3,(H,28,34)(H2,27,30,31)
• InChIKey: IRGGXYIIIARJBD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-4-{4-chloro-2-[2-(4-fluoro-1H-pyrazol-1-yl)ethoxy]-6-methylphenyl}-N-(2,2-difluoropropyl)-5H,6H,7H-pyrrolo[3,4-d]pyrimidine-6-carboxamide
• IUPAC Traditional name: 2-amino-4-{4-chloro-2-[2-(4-fluoropyrazol-1-yl)ethoxy]-6-methylphenyl}-N-(2,2-difluoropropyl)-5H,7H-pyrrolo[3,4-d]pyrimidine-6-carboxamide
• Synonyms: 2-Amino-4-[4-chloro-2-[2-(4-fluoro-1H-pyrazol-1-yl)ethoxy]-6-methylphenyl]-N-(2,2-difluoropropyl)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxamide; PF04942847; PF-4942847

Database IDs

• CAS Number: 1207961-33-8
• PubChem SID: 164232331
• PubChem CID: 46174270

CALCULATED PROPERTIES

• Acid pKa: 12.4757
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.86978
• LogD (pH = 7.4): 2.8702588
• Log P: 2.870268
• Molar Refractivity: 135.6528 cm^3
• Polarizability: 46.90569 Å^3
• Polar Surface Area: 111.19 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P294025

A novel potent, selective, and orally bioavailable pyrrolodinopyrimidine-containing inhibitor of heat shock protein 90 (Hsp90). It has been shown to induce degradation of multiple client proteins, cell-cycle block, apoptosis, and inhibits cell proliferati

REFERENCES

• Zehnder, L. et al.: J. Med. Chem., 54, 3368 (2011)
• Mehta, P.P. et al.: Clin. Cancer Res., 17, 5432 (2011)
• Yamakazi, S. et al.: J. Pharmacol. Exp. Therap., 338, 964 (2011)