3-chloro-4-(2-fluoro-4-(2-(N-phenylsulfamoyl)acetamido)phenoxy)picolinamide | 1612842-13-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-chloro-4-(2-fluoro-4-(2-(N-phenylsulfamoyl)acetamido)phenoxy)picolinamide
• CAS: 1612842-13-3
• 化学式: C₂₀H₁₆ClFN₄O₅S
• 分子量: 478.888
• InChiKey: NVZRKDIJRGFSOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  140.48
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-chloro-4-(2-fluoro-4-(2-(N-phenylsulfamoyl)acetamido)phenoxy)picolinamide 在 碘苯二乙酸 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 2.0h， 以67%的产率得到N-(4-((2-amino-3-chloropyridin-4-yl)oxy)-3-fluorophenyl)-2-(N-phenylsulfamoyl)acetamide
  参考文献：
  名称：

  Discovery of novel type II c-Met inhibitors based on BMS-777607

  摘要：

  Twenty-two new analogs based on the structure of BMS-777607 were designed, synthesized, and evaluated to determine their biological activities. Compounds bearing a cyclic sulfonamide or α-chloropiperidone scaffold exhibited good activity, which may provide a new basis for further structural optimization. Quinoline-containing analogs exhibited better results than did their counterparts with an aminopyrimidine, aminopyridine, or pyrrolopyridine unit. Two analogs, 22d and 22e, stood out as the most potent c-Met inhibitors with IC50s of 0.9 and 1.7 nM, respectively. These two compounds were more potent than BMS-777607 in enzymatic inhibition and cell proliferation studies.

  DOI：

  10.1016/j.ejmech.2014.04.056
• 作为产物：
  描述：

  ethyl 2-(N-phenylsulfamoyl)acetate 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 生成 3-chloro-4-(2-fluoro-4-(2-(N-phenylsulfamoyl)acetamido)phenoxy)picolinamide
  参考文献：
  名称：

  Discovery of novel type II c-Met inhibitors based on BMS-777607

  摘要：

  Twenty-two new analogs based on the structure of BMS-777607 were designed, synthesized, and evaluated to determine their biological activities. Compounds bearing a cyclic sulfonamide or α-chloropiperidone scaffold exhibited good activity, which may provide a new basis for further structural optimization. Quinoline-containing analogs exhibited better results than did their counterparts with an aminopyrimidine, aminopyridine, or pyrrolopyridine unit. Two analogs, 22d and 22e, stood out as the most potent c-Met inhibitors with IC50s of 0.9 and 1.7 nM, respectively. These two compounds were more potent than BMS-777607 in enzymatic inhibition and cell proliferation studies.

  DOI：

  10.1016/j.ejmech.2014.04.056