(5E)-5-[(4-{2-[(2H3)methyl(pyridin-2-yl)amino]ethoxy}phenyl)methylidene]-1,3-thiazolidine-2,4-dione

• ChemBase ID: 174225
• Molecular Formular: C18H17N3O3S
• Molecular Mass: 355.41088
• Monoisotopic Mass: 355.09906242
• SMILES: c1cccnc1N(CCOc1ccc(cc1)/C=C/1\C(=O)NC(=O)S1)C
• Canonical SMILES: O=C1NC(=O)/C(=C\c2ccc(cc2)OCCN(c2ccccn2)C)/S1
• InChI: InChI=1S/C18H17N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,12H,10-11H2,1H3,(H,20,22,23)/b15-12+
• InChIKey: HCDYSWMAMRPMST-NTCAYCPXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5E)-5-[(4-{2-[(^2H₃)methyl(pyridin-2-yl)amino]ethoxy}phenyl)methylidene]-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: (5E)-5-[(4-{2-[(^2H₃)methyl(pyridin-2-yl)amino]ethoxy}phenyl)methylidene]-1,3-thiazolidine-2,4-dione
• Synonyms: 5-[[4-[2-((Methyl-d3)-2-pyridinylamino)ethoxy]phenyl]methylene]-2,4-thiazolidinedione; 5-[4-[2-((Methyl-d3)pyridin-2-ylamino)ethoxy]benzylidene]thiazolidine-2,4-dione

Database IDs

• CAS Number: 1185245-57-1
• PubChem SID: 164230135
• PubChem CID: 46782303

CALCULATED PROPERTIES

• Polar Surface Area: 71.53 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true
• Acid pKa: 7.9180245
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.0845933
• LogD (pH = 7.4): 2.8161654
• Log P: 2.8223715
• Molar Refractivity: 99.3584 cm^3
• Polarizability: 37.233376 Å^3

PROPERTIES

Physical Property

• Solubility: Methanol

DETAILS

Toronto Research Chemicals - M326007

A labelled analog of the anti-diabetic drug Rosiglitazone.

REFERENCES

• Heath, C.M., et al.: J. Chem. Technol. Biotechnol., 68, 324 (1997)
• Lohray, B.B., et al.: J. Med. Chem., 41, 1619 (1997)