N-[1-(4-fluorobenzyl)piperidin-4-yl]-4-[[(2-chloro-6-methylquinazolin-4-yl)amino]methyl]benzamide | 1356125-07-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-[1-(4-fluorobenzyl)piperidin-4-yl]-4-[[(2-chloro-6-methylquinazolin-4-yl)amino]methyl]benzamide
• CAS: 1356125-07-9
• 化学式: C₂₉H₂₉ClFN₅O
• 分子量: 518.034
• InChiKey: LXSMUFUFUZGLSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  70.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-[1-(4-fluorobenzyl)piperidin-4-yl]-4-[[(2-chloro-6-methylquinazolin-4-yl)amino]methyl]benzamide 、 二甲胺 以150 mg的产率得到N-[1-(4-fluorobenzyl)piperidin-4-yl]-4-[[(2-(dimethylamino)-6-methylquinazolin-4-yl)amino]methyl]benzamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of New Diaminoquinazolines as β-Catenin/Tcf4 Pathway Inhibitors

  摘要：

  More than 50 new diaminoquinazoline derivatives have been synthesized and evaluated in a colon carcinoma cell growth inhibition assay using HCT116 and SW480 cells. Twenty compounds with good cell growth inhibitory activities (<4 mu M) were tested as inhibitors of the beta-catenin/T cell transcription factor 4 (Tcf4) signaling pathway using a HCT116 cell-based luciferase reporter assay. Results from the biological activities as well as the comparative molecular field analysis (CoMFA) of the properties of the molecules yielded a preliminary structure-activity relationship (SAR). Three potent compounds, 74, 78, and 86, showed IC50 values <1 mu M for growth inhibition of HCT116 cells and similar to 1 mu M for SW480 cells, as well as IC50 values of 1.5-2.5 mu M for HCT116 cells with the luciferase reporter assay.

  DOI：

  10.1021/jm201494a
• 作为产物：
  描述：

  4-叔丁氧羰基氨基哌啶 在 1-羟基苯并三唑 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 N-[1-(4-fluorobenzyl)piperidin-4-yl]-4-[[(2-chloro-6-methylquinazolin-4-yl)amino]methyl]benzamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of New Diaminoquinazolines as β-Catenin/Tcf4 Pathway Inhibitors

  摘要：

  More than 50 new diaminoquinazoline derivatives have been synthesized and evaluated in a colon carcinoma cell growth inhibition assay using HCT116 and SW480 cells. Twenty compounds with good cell growth inhibitory activities (<4 mu M) were tested as inhibitors of the beta-catenin/T cell transcription factor 4 (Tcf4) signaling pathway using a HCT116 cell-based luciferase reporter assay. Results from the biological activities as well as the comparative molecular field analysis (CoMFA) of the properties of the molecules yielded a preliminary structure-activity relationship (SAR). Three potent compounds, 74, 78, and 86, showed IC50 values <1 mu M for growth inhibition of HCT116 cells and similar to 1 mu M for SW480 cells, as well as IC50 values of 1.5-2.5 mu M for HCT116 cells with the luciferase reporter assay.

  DOI：

  10.1021/jm201494a