N,N-dimethyl-2-[2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethenyl]-6-quinolinamine | 1071778-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N,N-dimethyl-2-[2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethenyl]-6-quinolinamine
• 英文别名: 2-[2-(2,5-dimethyl-1-phenylpyrrol-3-yl)ethenyl]-N,N-dimethylquinolin-6-amine
• CAS: 1071778-66-9
• 化学式: C₂₅H₂₅N₃
• 分子量: 367.494
• InChiKey: PFYKNHDYTIWYDT-UHFFFAOYSA-N

物化性质

• 沸点：
  554.9±45.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  21.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-2-[2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethenyl]-6-quinolinamine 、 三氟甲烷磺酸甲酯 以 二氯甲烷 为溶剂， 反应 14.0h， 以52%的产率得到吡维铵
  参考文献：
  名称：

  New Synthesis of Pyrvinium That inhibits the β-Catenin/Tcf4 Pathway

  摘要：

  A new and converged route is described for synthesis of pyrvinium, an anthelmintic and antitumor agent. This method uses easily obtained materials and simple and practical reactions, including the key Friedlander condensation, to form the quinoline ring. The final product is generated through eight steps, with 23% yield and 96.6% purity (HPLC). This synthetic pyrvinium effectively inhibits beta-catenin/Tcf4 driven TOP-luciferase activity, with an IC50 value < 1 mu M, and induces colon cancer cell death in a dose-dependent manner with an IC50 of 0.54 +/- 0.06 mu M.

  DOI：

  10.3987/com-12-12446
• 作为产物：
  描述：

  5-氯-2-硝基苯甲醛 在 盐酸 、 氢气 、 sodium 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 24.0h， 生成 N,N-dimethyl-2-[2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethenyl]-6-quinolinamine
  参考文献：
  名称：

  New Synthesis of Pyrvinium That inhibits the β-Catenin/Tcf4 Pathway

  摘要：

  A new and converged route is described for synthesis of pyrvinium, an anthelmintic and antitumor agent. This method uses easily obtained materials and simple and practical reactions, including the key Friedlander condensation, to form the quinoline ring. The final product is generated through eight steps, with 23% yield and 96.6% purity (HPLC). This synthetic pyrvinium effectively inhibits beta-catenin/Tcf4 driven TOP-luciferase activity, with an IC50 value < 1 mu M, and induces colon cancer cell death in a dose-dependent manner with an IC50 of 0.54 +/- 0.06 mu M.

  DOI：

  10.3987/com-12-12446

文献信息

• New Synthesis of Pyrvinium That inhibits the β-Catenin/Tcf4 Pathway
  作者：Jing An、Yongjun Mao、Nan Lin、Wang Tian、Ziwei Huang

  DOI：10.3987/com-12-12446

  日期：——

  A new and converged route is described for synthesis of pyrvinium, an anthelmintic and antitumor agent. This method uses easily obtained materials and simple and practical reactions, including the key Friedlander condensation, to form the quinoline ring. The final product is generated through eight steps, with 23% yield and 96.6% purity (HPLC). This synthetic pyrvinium effectively inhibits beta-catenin/Tcf4 driven TOP-luciferase activity, with an IC50 value < 1 mu M, and induces colon cancer cell death in a dose-dependent manner with an IC50 of 0.54 +/- 0.06 mu M.