7-(3-(1H-1,2,4-triazol-1-yl)propoxy)-4-chloro-6-methoxyquinoline | 1061610-60-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-(3-(1H-1,2,4-triazol-1-yl)propoxy)-4-chloro-6-methoxyquinoline
• CAS: 1061610-60-3
• 化学式: C₁₅H₁₅ClN₄O₂
• 分子量: 318.763
• InChiKey: AXXPPWZVCWBPKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  62.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-benzyl-5-(3-fluoro-4-hydroxyphenyl)-3-methylpyrimidin-4(3H)-one 、 7-(3-(1H-1,2,4-triazol-1-yl)propoxy)-4-chloro-6-methoxyquinoline 在 吡啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.17h， 以3%的产率得到2-benzyl-5-(3-fluoro-4-(6-methoxy-7-(3-(1H-1,2,4-triazol-1-yl)propoxy)quinolin-4-yloxy)-phenyl)-3-methylpyrimidin-4(3H)-one
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Potent c-Met Inhibitors

  摘要：

  c-Met is a receptor tyrosine kinase that plays a key role in several cellular processes but has also been found to be overexpressed and mutated in different human cancers. Consequently, targeting this enzyme has become an area of intense research in drug discovery. Our studies began with the design and synthesis of novel pyrimidone 7, which was found to be a potent c-Met inhibitor. Subsequent SAR studies identified 22 as a more potent analog, whereas an X-ray crystal structure of 7 bound to c-Met revealed an unexpected binding conformation. This latter finding led to the development of a new series that featured compounds that were more potent both in vitro and in vivo than 22 and also exhibited different binding conformations to c-Met. Novel c-Met inhibitors have been designed, developed, and found to be potent in vitro and in vivo.

  DOI：

  10.1021/jm8006189
• 作为产物：
  描述：

  1H-1,2,4-三唑 、 4-chloro-7-(3-chloropropoxy)-6-methoxyquinoline 在 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 7-(3-(1H-1,2,4-triazol-1-yl)propoxy)-4-chloro-6-methoxyquinoline
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Potent c-Met Inhibitors

  摘要：

  c-Met is a receptor tyrosine kinase that plays a key role in several cellular processes but has also been found to be overexpressed and mutated in different human cancers. Consequently, targeting this enzyme has become an area of intense research in drug discovery. Our studies began with the design and synthesis of novel pyrimidone 7, which was found to be a potent c-Met inhibitor. Subsequent SAR studies identified 22 as a more potent analog, whereas an X-ray crystal structure of 7 bound to c-Met revealed an unexpected binding conformation. This latter finding led to the development of a new series that featured compounds that were more potent both in vitro and in vivo than 22 and also exhibited different binding conformations to c-Met. Novel c-Met inhibitors have been designed, developed, and found to be potent in vitro and in vivo.

  DOI：

  10.1021/jm8006189