(3R,4S)-3-hydroxy-2,2-dimethyl-4-(2-oxopyrrolidin-1-yl)-3,4-dihydro-2H-1-benzopyran-6-carbonitrile

• ChemBase ID: 165036
• Molecular Formular: C16H18N2O3
• Molecular Mass: 286.32572
• Monoisotopic Mass: 286.13174245
• SMILES: c1c(cc2c(c1)OC([C@@H]([C@H]2N1CCCC1=O)O)(C)C)C#N
• Canonical SMILES: N#Cc1ccc2c(c1)[C@H](N1CCCC1=O)[C@H](C(O2)(C)C)O
• InChI: InChI=1S/C16H18N2O3/c1-16(2)15(20)14(18-7-3-4-13(18)19)11-8-10(9-17)5-6-12(11)21-16/h5-6,8,14-15,20H,3-4,7H2,1-2H3/t14-,15+/m0/s1
• InChIKey: TVZCRIROJQEVOT-LSDHHAIUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S)-3-hydroxy-2,2-dimethyl-4-(2-oxopyrrolidin-1-yl)-3,4-dihydro-2H-1-benzopyran-6-carbonitrile
• IUPAC Traditional name: cromakalim
• Synonyms: 3-[(1R)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-5-[1-(4-piperidinyl-d4)-1H-pyrazol-4-yl]-2-pyridinamine; (R)-3-[1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl-d4)-1H-pyrazol-4-yl]pyridin-2-ylamine; PF 02341066-d4; PF 2341066-d4; [3-[[(R)-1-(2,6-Dichloro-3-fluorophenyl)ethyl]oxy]-5-[1-(piperidin-4-yl-d4)-1H-pyrazol-4-yl]pyridin-2-yl]amine; Crizotinib-d4

Database IDs

• PubChem SID: 162259169
• PubChem CID: 71191

CALCULATED PROPERTIES

• Acid pKa: 13.255401
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.0220234
• LogD (pH = 7.4): 1.0220231
• Log P: 1.0220237
• Molar Refractivity: 76.6727 cm^3
• Polarizability: 29.792604 Å^3
• Polar Surface Area: 73.56 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C785002

Labelled Crizotinib(C78500). A potent and selective dual inhibitor of mesenchymal-epithelial transition factor (c-MET) kinase and anaplastic lymphoma kinase (ALK). Crizotinib is a potential antitumor agent.

REFERENCES

• Zou, H.Y. et al.: Cancer Res., 67, 4408 (2007)
• Cui, J.J. et al.: J. Med. Chem., No pp given (2007)
• Sasaki, T. et al.: Cancer. Res. et al.: 70, 10038 (2007)