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

• ChemBase ID: 153301
• Molecular Formular: C21H17N3O2S
• Molecular Mass: 375.44358
• Monoisotopic Mass: 375.1041478
• SMILES: Cc1cc(c(n1c1cccnc1)C)/C=C\1/C(=O)N(C(=O)S1)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
• InChIKey: NCSHZXNGQYSKLR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 677331-12-3
• MDL Number: MFCD04366833
• PubChem SID: 162247440
• PubChem CID: 5967294

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: 41.386265 Å^3
• Polar Surface Area: 55.2 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: yellow to orange powder

Safety Information

• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H17N3O2S

DETAILS

Sigma Aldrich - SML0203

Biochem/physiol Actions
iCRT14 is a Wnt / β-catenin pathway inhibitor. It is a potent inhibitor of Catenin Responsive Transcription (CRT) reporter genes, as well as endogenous gene targets. iCRT14 also disrupts β-catenin-TCF4 interaction in a dose dependent manner, and causes G0/G1 arrest in colon tumor lines.

Toronto Research Chemicals - I163900

A 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 arrest in HCT-

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)