ethyl 2-(carbamoylsulfanyl)-3-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}propanoate

• ChemBase ID: 159908
• Molecular Formular: C21H26N2O4S
• Molecular Mass: 402.50714
• Monoisotopic Mass: 402.16132832
• SMILES: n1cc(ccc1CCOc1ccc(cc1)CC(SC(=O)N)C(=O)OCC)CC
• Canonical SMILES: CCOC(=O)C(Cc1ccc(cc1)OCCc1ccc(cn1)CC)SC(=O)N
• InChI: InChI=1S/C21H26N2O4S/c1-3-15-5-8-17(23-14-15)11-12-27-18-9-6-16(7-10-18)13-19(28-21(22)25)20(24)26-4-2/h5-10,14,19H,3-4,11-13H2,1-2H3,(H2,22,25)
• InChIKey: ITXRIKOYRWVLAY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-(carbamoylsulfanyl)-3-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}propanoate
• IUPAC Traditional name: ethyl 2-(carbamoylsulfanyl)-3-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}propanoate
• Synonyms: Pioglitazone Impurity E (EP); α-[(Aminocarbonyl)thio]-4-[2-(5-ethyl-2-pyridinyl)ethoxy]benzenepropanoic Acid Ethyl Ester(Pioglitazone Impurity)

Database IDs

• CAS Number: 868754-41-0
• PubChem SID: 162254043
• PubChem CID: 46780227

CALCULATED PROPERTIES

• Acid pKa: 16.355448
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.5066295
• LogD (pH = 7.4): 3.8564286
• Log P: 3.8636785
• Molar Refractivity: 109.9863 cm^3
• Polarizability: 43.04593 Å^3
• Polar Surface Area: 91.51 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 89-91C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A603065

A novel pharmaceutical formulation containing a biguanide and a thiazolidinedione derivative. Pioglitazone (P471000) derivative.

REFERENCES

• Wagner, E.R., et al.: J. Med. Chem., 20, 1007 (1977)
• Kawamatsu, Y., et al.: Arzneim.-Forsch., 30, 751 (1977)
• Sohda, T., et al.: Chem. Pharm. Bull., 30, 3580 (1977)
• Iwai, H., et al.: Biochem. Pharmacol., 32, 849 (1977)