(5Z)-5-({4-[2-(5-ethylpyridin-2-yl)(2H4)ethoxy]phenyl}methylidene)-1,3-thiazolidine-2,4-dione

• ChemBase ID: 168740
• Molecular Formular: C19H18N2O3S
• Molecular Mass: 354.42282
• Monoisotopic Mass: 354.10381345
• SMILES: n1cc(ccc1CCOc1ccc(cc1)/C=C\1/C(=O)NC(=O)S1)CC
• Canonical SMILES: CCc1ccc(nc1)CCOc1ccc(cc1)/C=C/1\SC(=O)NC1=O
• InChI: InChI=1S/C19H18N2O3S/c1-2-13-3-6-15(20-12-13)9-10-24-16-7-4-14(5-8-16)11-17-18(22)21-19(23)25-17/h3-8,11-12H,2,9-10H2,1H3,(H,21,22,23)/b17-11-
• InChIKey: YNTUJOCADSTMCL-BOPFTXTBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-5-({4-[2-(5-ethylpyridin-2-yl)(^2H₄)ethoxy]phenyl}methylidene)-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: (5Z)-5-({4-[2-(5-ethylpyridin-2-yl)(^2H₄)ethoxy]phenyl}methylidene)-1,3-thiazolidine-2,4-dione
• Synonyms: 5-[4-[2-(5-Ethylpyridin-2-yl)ethoxy-d4]benzylidene]thiazolidine-2,4-dione; 5-[[4-[2-(5-Ethyl-2-pyridinyl)ethoxy-d4]phenyl]methylene]-2,4-thiazolidinedione; 5-[4-[2-(5-Ethylpyridin-2-yl)ethoxy]benzylidene]thiazolidine-2,4-dione; Didehydropioglitazone; 5-[[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]-methylene]-2,4-thiazolidinedione(Pioglitazone Impurity)

Database IDs

• CAS Number: 144809-28-9
• PubChem SID: 162262872
• PubChem CID: 45039221

CALCULATED PROPERTIES

• Molar Refractivity: 98.9593 cm^3
• Polarizability: 37.850243 Å^3
• Polar Surface Area: 68.29 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true
• Acid pKa: 7.905028
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.1168187
• LogD (pH = 7.4): 3.3511715
• Log P: 3.475563

PROPERTIES

Physical Property

• Solubility: Dimethylformamide; DMSO; Methanol
• Apperance: Off-White Solid; White Solid
• Melting Point: 156-159°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E925592

A novel labelled intermediate of Pioglitazone (P471000).

Toronto Research Chemicals - E925590

A novel intermediate of Pioglitazone (P471000).

REFERENCES

• Diaz, J., et al.: J. Biol. Chem., 272, 11350 (1997)
• Day, C., et al.: Diabet Med., 16, 179 (1997)
• Motomura, W., et al.: Cancer Res., 60, 5558 (1997)
• Koeffler, H., et al.: Clin. Cancer Res., 9, 1 (1997)
• Diaz, J., et al.: J. Biol. Chem., 272, 11350 (1997)
• Day, C., et al.: Diabet Med., 16, 179 (1997)
• Motomura, W., et al.: Cancer Res., 60, 5558 (1997)
• Koeffler, H., et al.: Clin. Cancer Res., 9, 1 (1997)