2-[5-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-2-methoxypyridin-3-yl]-3H-benzimidazole-5-carboxylic acid | 1429297-54-0

• 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: 2-[5-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-2-methoxypyridin-3-yl]-3H-benzimidazole-5-carboxylic acid
• CAS: 1429297-54-0
• 化学式: C₂₂H₁₆Cl₂FN₃O₄
• 分子量: 476.291
• InChiKey: CDNWPTPVYCXELR-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[5-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-2-methoxypyridin-3-yl]-3H-benzimidazole-5-carboxylic acid 在 三甲基氯硅烷 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 2-[5-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-2-oxo-1H-pyridin-3-yl]-N-(2-morpholin-4-ylethyl)-3H-benzimidazole-5-carboxamide
  参考文献：
  名称：

  Novel 5-(benzyloxy)pyridin-2(1H)-one derivatives as potent c-Met inhibitors

  摘要：

  A series of novel 5-(benzyloxy)pyridin-2(1H)-ones were designed, synthesized and biologically evaluated for c-Met inhibition. Various amides and benzoimidazoles at C-3 position were investigated. A potent compound 12b with a c-Met IC50 of 12 nM was identified. This compound exhibited potent inhibition of EBC-1 cell associated with c-Met constitutive activation and showed high selectivity for c-Met than other tested 11 kinases. The binding model 12b with c-Met was disclosed by docking analysis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.037
• 作为产物：
  描述：

  methyl 5-hydroxy-2-methoxypyridinecarboxylate 在 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 sodium hydrogensulfite 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 生成 2-[5-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-2-methoxypyridin-3-yl]-3H-benzimidazole-5-carboxylic acid
  参考文献：
  名称：

  Novel 5-(benzyloxy)pyridin-2(1H)-one derivatives as potent c-Met inhibitors

  摘要：

  A series of novel 5-(benzyloxy)pyridin-2(1H)-ones were designed, synthesized and biologically evaluated for c-Met inhibition. Various amides and benzoimidazoles at C-3 position were investigated. A potent compound 12b with a c-Met IC50 of 12 nM was identified. This compound exhibited potent inhibition of EBC-1 cell associated with c-Met constitutive activation and showed high selectivity for c-Met than other tested 11 kinases. The binding model 12b with c-Met was disclosed by docking analysis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.037

文献信息

• Novel 5-(benzyloxy)pyridin-2(1H)-one derivatives as potent c-Met inhibitors
  作者：Dengyou Zhang、Jing Ai、Zhongjie Liang、Wei Zhu、Xia Peng、Xianjie Chen、YinChun Ji、Hualiang Jiang、Cheng Luo、Meiyu Geng、Hong Liu

  DOI：10.1016/j.bmcl.2013.02.037

  日期：2013.4

  A series of novel 5-(benzyloxy)pyridin-2(1H)-ones were designed, synthesized and biologically evaluated for c-Met inhibition. Various amides and benzoimidazoles at C-3 position were investigated. A potent compound 12b with a c-Met IC50 of 12 nM was identified. This compound exhibited potent inhibition of EBC-1 cell associated with c-Met constitutive activation and showed high selectivity for c-Met than other tested 11 kinases. The binding model 12b with c-Met was disclosed by docking analysis. (C) 2013 Elsevier Ltd. All rights reserved.