2-amino-5-bromo-N-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethyl]pyridine-3-carboxamide | 1394930-83-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-amino-5-bromo-N-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethyl]pyridine-3-carboxamide
• CAS: 1394930-83-6
• 化学式: C₁₄H₁₁BrCl₂FN₃O
• 分子量: 407.069
• InChiKey: COQLQLVKPZPMAH-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  68.01
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(四氢吡喃-4-基)-1H-吡唑-4-硼酸频哪醇酯 、 2-amino-5-bromo-N-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethyl]pyridine-3-carboxamide 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 18.0h， 以35%的产率得到2-amino-N-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-[1-(oxan-4-yl)pyrazol-4-yl]pyridine-3-carboxamide
  参考文献：
  名称：

  Discovery of novel 2-aminopyridine-3-carboxamides as c-Met kinase inhibitors

  摘要：

  A series of 2-aminopyridine-3-carboxamide derivatives against c-Met were designed and synthesized by employing bioisosteric replacement of heterocyclic moieties with the amide bond. The structure-activity relationship (SAR) at various positions of the scaffold was explored. In this study, a promising compound (S)-24o with a c-Met IC50 of 0.022 mu M was identified. The compound exhibited dose-dependent inhibition of the phosphorylation of c-Met as well as downstream signaling in EBC-1 cells. Furthermore, the interactive binding model of (S)-24o with c-Met was elucidated by virtue of a molecular modeling study. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.007
• 作为产物：
  描述：

  (S)-1-(2,6-二氯-3-氟苯基)乙醇 在 sodium azide 、 氯化铵 、 三乙胺 、 锌 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-amino-5-bromo-N-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethyl]pyridine-3-carboxamide
  参考文献：
  名称：

  Discovery of novel 2-aminopyridine-3-carboxamides as c-Met kinase inhibitors

  摘要：

  A series of 2-aminopyridine-3-carboxamide derivatives against c-Met were designed and synthesized by employing bioisosteric replacement of heterocyclic moieties with the amide bond. The structure-activity relationship (SAR) at various positions of the scaffold was explored. In this study, a promising compound (S)-24o with a c-Met IC50 of 0.022 mu M was identified. The compound exhibited dose-dependent inhibition of the phosphorylation of c-Met as well as downstream signaling in EBC-1 cells. Furthermore, the interactive binding model of (S)-24o with c-Met was elucidated by virtue of a molecular modeling study. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.007