(5E)-5-({3-bromo-4-[2-cyclohexyl(2H4)ethoxy]phenyl}methylidene)-1,3-thiazolidine-2,4-dione

• ChemBase ID: 162679
• Molecular Formular: C18H20BrNO3S
• Molecular Mass: 410.3253
• Monoisotopic Mass: 409.03472651
• SMILES: S1/C(=C/c2ccc(c(c2)Br)OCCC2CCCCC2)/C(=O)NC1=O
• Canonical SMILES: O=C1NC(=O)/C(=C\c2ccc(c(c2)Br)OCCC2CCCCC2)/S1
• InChI: InChI=1S/C18H20BrNO3S/c19-14-10-13(11-16-17(21)20-18(22)24-16)6-7-15(14)23-9-8-12-4-2-1-3-5-12/h6-7,10-12H,1-5,8-9H2,(H,20,21,22)/b16-11+
• InChIKey: NNJXJDRXWLCJSS-LFIBNONCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5E)-5-({3-bromo-4-[2-cyclohexyl(^2H₄)ethoxy]phenyl}methylidene)-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: (5E)-5-({3-bromo-4-[2-cyclohexyl(^2H₄)ethoxy]phenyl}methylidene)-1,3-thiazolidine-2,4-dione
• Synonyms: 5-[[3-Bromo-4-(2-cyclohexylethoxy)phenyl]methylene]-2,4-thiazolidinedione-d4

Database IDs

• PubChem SID: 162256814
• PubChem CID: 71314184

CALCULATED PROPERTIES

• Acid pKa: 7.652635
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.938928
• LogD (pH = 7.4): 4.7518687
• Log P: 4.9419384
• Molar Refractivity: 100.73 cm^3
• Polarizability: 38.657112 Å^3
• Polar Surface Area: 55.4 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B682757

Labelled derivative of 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)