N-(2-(3,4-dichlorophenyl)-1H-benzo[d]imidazol-6-yl)quinazolin-4-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: N-(2-(3,4-dichlorophenyl)-1H-benzo[d]imidazol-6-yl)quinazolin-4-amine
• 英文别名: N-[2-(3,4-dichlorophenyl)-3H-benzimidazol-5-yl]quinazolin-4-amine
• 化学式: C₂₁H₁₃Cl₂N₅
• 分子量: 406.274
• InChiKey: KLXHHAKVXAIRBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4-二氯苯甲酸 在 铁粉 、 溶剂黄146 作用下， 以 乙醇 、 水 、 异丙醇 为溶剂， 反应 12.0h， 生成 N-(2-(3,4-dichlorophenyl)-1H-benzo[d]imidazol-6-yl)quinazolin-4-amine
  参考文献：
  名称：

  Discovery of quinazolin-4-amines bearing benzimidazole fragments as dual inhibitors of c-Met and VEGFR-2

  摘要：

  Both c-Met and VEGFR-2 are important targets for the treatment of cancers. In this study, a series of N-(2-phenyl-1H-benzo[d]imidazol-5-yl)quinazolin-4-amine derivatives were designed and identified as dual c-Met and VEGFR-2 inhibitors. Among these compounds bearing quinazoline and benzimidazole fragments, compound 7j exhibited the most potent inhibitory activity against c-Met and VEGFR-2 with IC50 of 0.05μM and 0.02μM, respectively. It also showed the highest anticancer activity against the tested cancer cell lines with IC50 of 1.5μM against MCF-7 and 8.7μM against Hep-G2. Docking simulation supported the initial pharmacophoric hypothesis and suggested a common mode of interaction at the ATP-binding site of c-Met and VEGFR-2, which demonstrates that compound 7j is a potential agent for cancer therapy deserving further researching.

  DOI：

  10.1016/j.bmc.2014.07.008

文献信息

• Discovery of quinazolin-4-amines bearing benzimidazole fragments as dual inhibitors of c-Met and VEGFR-2
  作者：Lei Shi、Ting-Ting Wu、Zhi Wang、Jia-Yu Xue、Yun-Gen Xu

  DOI：10.1016/j.bmc.2014.07.008

  日期：2014.9

  Both c-Met and VEGFR-2 are important targets for the treatment of cancers. In this study, a series of N-(2-phenyl-1H-benzo[d]imidazol-5-yl)quinazolin-4-amine derivatives were designed and identified as dual c-Met and VEGFR-2 inhibitors. Among these compounds bearing quinazoline and benzimidazole fragments, compound 7j exhibited the most potent inhibitory activity against c-Met and VEGFR-2 with IC50 of 0.05μM and 0.02μM, respectively. It also showed the highest anticancer activity against the tested cancer cell lines with IC50 of 1.5μM against MCF-7 and 8.7μM against Hep-G2. Docking simulation supported the initial pharmacophoric hypothesis and suggested a common mode of interaction at the ATP-binding site of c-Met and VEGFR-2, which demonstrates that compound 7j is a potential agent for cancer therapy deserving further researching.