(5Z)-5-{[2,5-dimethyl-1-(pyridin-3-yl)-1H-pyrrol-3-yl]methylidene}-3-(2H5)phenyl-1,3-thiazolidine-2,4-dione

• ChemBase ID: 171504
• Molecular Formular: C21H17N3O2S
• Molecular Mass: 375.44358
• Monoisotopic Mass: 375.1041478
• SMILES: c1c(c(n(c1C)c1cnccc1)C)/C=C/1\SC(=O)N(C1=O)c1ccccc1
• Canonical SMILES: O=C1S/C(=C\c2cc(n(c2C)c2cccnc2)C)/C(=O)N1c1ccccc1
• InChI: InChI=1S/C21H17N3O2S/c1-14-11-16(15(2)23(14)18-9-6-10-22-13-18)12-19-20(25)24(21(26)27-19)17-7-4-3-5-8-17/h3-13H,1-2H3/b19-12-
• InChIKey: NCSHZXNGQYSKLR-UNOMPAQXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-5-{[2,5-dimethyl-1-(pyridin-3-yl)-1H-pyrrol-3-yl]methylidene}-3-(^2H₅)phenyl-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: (5Z)-5-{[2,5-dimethyl-1-(pyridin-3-yl)pyrrol-3-yl]methylidene}-3-(^2H₅)phenyl-1,3-thiazolidine-2,4-dione
• Synonyms: 5-[[2,5-Dimethyl-1-(3-pyridinyl)-1H-pyrrol-3-yl]methylene]-3-(phenyl-d5)-2,4-thiazolidinedione; iCRT 14-d5; iCRT14-d5; iCRT-14-d5

Database IDs

• PubChem SID: 164227414
• PubChem CID: 71749442

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.480733
• LogD (pH = 7.4): 2.678992
• Log P: 2.6824
• Molar Refractivity: 118.7902 cm^3
• Polarizability: 41.410732 Å^3
• Polar Surface Area: 55.2 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I163902

A labelled potent inhibitor of β-catenin-responsive transcription (CRT) (IC50 = 40.3 nM in assays of Wnt pathway activity). Studies suggest that it may directly influence the interaction between β-catenin and TCF4. It induces marked G0/G1 cell cycle arres

REFERENCES

• Gonsalves, F.C. et al.: Proc. Natl. Acad. Sci. USA, 108, 5954 (2011)
• Watanabe, K. et al.: Proc. Natl. Acad. Sci. USA, 108, 5929 (2011)