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

• ChemBase ID: 177604
• Molecular Formular: C18H19N3O3S
• Molecular Mass: 357.42676
• Monoisotopic Mass: 357.11471248
• SMILES: c1cccnc1N(CCOc1ccc(cc1)CC1C(=O)NC(=O)S1)C
• Canonical SMILES: O=C1NC(=O)C(S1)Cc1ccc(cc1)OCCN(c1ccccn1)C
• InChI: InChI=1S/C18H19N3O3S/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/h2-9,15H,10-12H2,1H3,(H,20,22,23)
• InChIKey: YASAKCUCGLMORW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(4-{2-[(^2H₃)methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: 5-[(4-{2-[(^2H₃)methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione
• Synonyms: 5-[[4-[2-((Methyl-d3)-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione; BRL-49653-d3; Rosiglitazone-d3

Database IDs

• PubChem SID: 164233514
• PubChem CID: 25225106

CALCULATED PROPERTIES

• Lipinski's Rule of Five: true
• Acid pKa: 6.844312
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.151827
• LogD (pH = 7.4): 2.2077625
• Log P: 2.446348
• Molar Refractivity: 97.7899 cm^3
• Polarizability: 37.404324 Å^3
• Polar Surface Area: 71.53 Å^2
• Rotatable Bonds: 7

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 149-151°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - R693502

Labelled Rosiglitazone. Insulin sensitizer; binds to peroxisome proliferator activated receptor gamma (PPAR- γ).

REFERENCES

• Cantello, B.C.C., et al.: J. Med. Chem., 37, 3977 (1994)
• Oakes, N.D., et al.: Diabetes, 43, 1203 (1994)
• Balton, G.C., et al.: Xenobiotica, 26, 627 (1994)
• Barman, J.A., et al.: Drugs, 57, 921 (1994)