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

• ChemBase编号: 153301
• 分子式: C21H17N3O2S
• 平均质量: 375.44358
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 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传统名: 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
• 别名: 5-[[2,5-Dimethyl-1-(3-pyridinyl)-1H-pyrrol-3-yl]methylene]-3-phenyl-2,4-thiazolidinedione; iCRT14; iCRT 14; iCRT14; iCRT-14

登记号

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

理论计算性质

• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 2.480733
• LogD (pH = 7.4): 2.678992
• Log P: 2.6824
• 摩尔折射率: 118.7902 cm^3
• 极化性: 41.386265 Å^3
• 极化表面积: 55.2 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: ≥10 mg/mL
• 外观: yellow to orange powder

安全信息

• 保存温度: 2-8°C

产品相关信息

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

详细说明

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-

参考文献

• 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)