methyl 2-(4-amino-6-chloro-1,3,5-triazin-2-ylamino)benzoate | 1374227-27-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-(4-amino-6-chloro-1,3,5-triazin-2-ylamino)benzoate
• 英文别名: Methyl 2-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]benzoate
• CAS: 1374227-27-6
• 化学式: C₁₁H₁₀ClN₅O₂
• 分子量: 279.686
• InChiKey: ZFWNLUKSPOVFFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-amino-6-chloro-1,3,5-triazin-2-ylamino)benzoate 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 calcium chloride 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 N-methyl-2-[4-(3,4,5-trimethoxyphenylamino)imidazo[1,2-a][1,3,5]triazin-2-ylamino]benzamide
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Novel Imidazo[1,2-a][1,3,5]triazines and Their Derivatives as Focal Adhesion Kinase Inhibitors with Antitumor Activity

  摘要：

  A series of triazinic inhibitors of focal adhesion kinase (FAK) have been recently shown to exert antiangiogenic activity against HUVEC cells and anticancer efficacy against several cancer cell lines. We report herein that we further explored the heterocyclic core of these inhibitors by a fused imidazole ring with the triazine to provide imidazo[1,2-a][1,3,5]triazines. Importantly, these new compounds displayed 10(-7-)10(-8) M IC50 values, and the best inhibitor showed IC50 value of 50 nM against FAK enzymatic activity. Several inhibitors potently inhibited the proliferation of a panel of cancer cell lines expressing high levels of FAK. Apoptosis analysis in U87-MG and HCT-116 cell lines suggested that these compounds delayed cell cycle progression by arresting cells in the G2/M phase of the cell cycle, retarding cell growth. Further investigation demonstrated that these compounds strongly inhibited cell-matrix adhesion, migration, and invasion of U87-MG cells.

  DOI：

  10.1021/jm500784e
• 作为产物：
  描述：

  methyl 2-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]benzoate 在 氨 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 生成 methyl 2-(4-amino-6-chloro-1,3,5-triazin-2-ylamino)benzoate
  参考文献：
  名称：

  High yielding microwave-assisted synthesis of tri-substituted 1,3,5-triazines using Pd-catalyzed aryl and heteroarylamination

  摘要：

  A rapid and efficient Pd-catalyzed aryl and heteroarylamination under microwave irradiation has been developed for various tri-substituted triazines that can serve as versatile building blocks for both supramolecular and medicinal chemistry research. Particularly valuable features of this method included the short reaction time, good yield, and convenient operation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.041

文献信息

• High yielding microwave-assisted synthesis of tri-substituted 1,3,5-triazines using Pd-catalyzed aryl and heteroarylamination
  作者：Pascal Dao、Christiane Garbay、Huixiong Chen

  DOI：10.1016/j.tet.2012.03.041

  日期：2012.5

  A rapid and efficient Pd-catalyzed aryl and heteroarylamination under microwave irradiation has been developed for various tri-substituted triazines that can serve as versatile building blocks for both supramolecular and medicinal chemistry research. Particularly valuable features of this method included the short reaction time, good yield, and convenient operation. (C) 2012 Elsevier Ltd. All rights reserved.
• Design, Synthesis, and Evaluation of Novel Imidazo[1,2-<i>a</i>][1,3,5]triazines and Their Derivatives as Focal Adhesion Kinase Inhibitors with Antitumor Activity
  作者：Pascal Dao、Nikaia Smith、Céline Tomkiewicz-Raulet、Expédite Yen-Pon、Marta Camacho-Artacho、Daniel Lietha、Jean-Phillipe Herbeuval、Xavier Coumoul、Christiane Garbay、Huixiong Chen

  DOI：10.1021/jm500784e

  日期：2015.1.8

  A series of triazinic inhibitors of focal adhesion kinase (FAK) have been recently shown to exert antiangiogenic activity against HUVEC cells and anticancer efficacy against several cancer cell lines. We report herein that we further explored the heterocyclic core of these inhibitors by a fused imidazole ring with the triazine to provide imidazo[1,2-a][1,3,5]triazines. Importantly, these new compounds displayed 10(-7-)10(-8) M IC50 values, and the best inhibitor showed IC50 value of 50 nM against FAK enzymatic activity. Several inhibitors potently inhibited the proliferation of a panel of cancer cell lines expressing high levels of FAK. Apoptosis analysis in U87-MG and HCT-116 cell lines suggested that these compounds delayed cell cycle progression by arresting cells in the G2/M phase of the cell cycle, retarding cell growth. Further investigation demonstrated that these compounds strongly inhibited cell-matrix adhesion, migration, and invasion of U87-MG cells.