6-bromo-3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-3H,4H-pyrido[2,3-d]pyrimidin-4-one | 1394930-38-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6-bromo-3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-3H,4H-pyrido[2,3-d]pyrimidin-4-one
• CAS: 1394930-38-1
• 化学式: C₁₅H₉BrCl₂FN₃O
• 分子量: 417.064
• InChiKey: BEZYNPBKFXMREB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  47.78
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-bromo-3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-3H,4H-pyrido[2,3-d]pyrimidin-4-one 在 四(三苯基膦)钯 、 potassium fluoride dihydrate 、 三氟乙酸 作用下， 以 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 2.83h， 生成 3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-6-(1-piperidin-4-ylpyrazol-4-yl)pyrido[2,3-d]pyrimidin-4-one
  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：

  1-(2,6-二氯-3-氟苯基)乙醇 在 4-二甲氨基吡啶 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 5.0h， 生成 6-bromo-3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-3H,4H-pyrido[2,3-d]pyrimidin-4-one
  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