(5E)-5-{[4-(2-cyclohexylethoxy)-3-methoxyphenyl]methylidene}-1,3-thiazolidine-2,4-dione

• ChemBase ID: 165205
• Molecular Formular: C19H23NO4S
• Molecular Mass: 361.45522
• Monoisotopic Mass: 361.13477922
• SMILES: S1/C(=C/c2ccc(c(c2)OC)OCCC2CCCCC2)/C(=O)NC1=O
• Canonical SMILES: COc1cc(ccc1OCCC1CCCCC1)/C=C\1/SC(=O)NC1=O
• InChI: InChI=1S/C19H23NO4S/c1-23-16-11-14(12-17-18(21)20-19(22)25-17)7-8-15(16)24-10-9-13-5-3-2-4-6-13/h7-8,11-13H,2-6,9-10H2,1H3,(H,20,21,22)/b17-12+
• InChIKey: REFPRDWFDSQKAG-SFQUDFHCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5E)-5-{[4-(2-cyclohexylethoxy)-3-methoxyphenyl]methylidene}-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: (5E)-5-{[4-(2-cyclohexylethoxy)-3-methoxyphenyl]methylidene}-1,3-thiazolidine-2,4-dione
• Synonyms: 5-[[4-(2-Cyclohexylethoxy)-3-methoxyphenyl]methylene]-2,4-thiazolidinedione

Database IDs

• CAS Number: 1239610-60-6
• PubChem SID: 162259338
• PubChem CID: 71315078

CALCULATED PROPERTIES

• Acid pKa: 7.9026146
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.013819
• LogD (pH = 7.4): 3.8983643
• Log P: 4.015515
• Molar Refractivity: 99.5704 cm^3
• Polarizability: 38.395943 Å^3
• Polar Surface Area: 64.63 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C988015

A thiazolidinedione analogue prepared for use as a 15-hydroxyprostaglandin dehydrogenase (15-PGDH) inhibitor and wound healing promoter.

REFERENCES

• Wu, Y. et al.: J. Med. Chem., 54, 5260 (2011)