ethyl 3-(5-acetyl-2-aminophenyl)acrylate | 1253972-45-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-(5-acetyl-2-aminophenyl)acrylate
• 英文别名: 3-(5-acetyl-2-aminophenyl)acrylic acid ethyl ester；Ethyl 3-(5-acetyl-2-aminophenyl)prop-2-enoate
• CAS: 1253972-45-0
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: KMBPEKUAPGAJGB-UHFFFAOYSA-N

物化性质

• 沸点：
  431.4±40.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-(5-acetyl-2-aminophenyl)acrylate 在 盐酸 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 4.0h， 以60%的产率得到6-acetylquinolin-2(1H)-one
  参考文献：
  名称：

  [EN] INHIBITORS OF ACETYL-COA CARBOXYLASE
  [FR] INHIBITEURS DE L'ACÉTYL-COA CARBOXYLASE

  摘要：

  本发明涉及作为乙酰辅酶A羧化酶（ACC）抑制剂的化合物。该发明还涉及制备这些化合物的方法、含有这些化合物的组合物，以及使用这些化合物进行治疗的方法。

  公开号：

  WO2010127208A1
• 作为产物：
  描述：

  4-氨基苯乙酮 在 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex 、 一氯化碘 、 三乙胺 、 calcium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 ethyl 3-(5-acetyl-2-aminophenyl)acrylate
  参考文献：
  名称：

  Identification of 3-substituted-6-(1-(1 H -[1,2,3]triazolo[4,5- b ]pyrazin-1-yl)ethyl)quinoline derivatives as highly potent and selective mesenchymal-epithelial transition factor (c-Met) inhibitors via metabolite profiling-based structural optimization

  摘要：

  c-Met/HGF signaling pathway plays an important role in cancer progression, and it was considered to be related to poor prognosis and drug resistance. Based on metabolite profiling of (S)-7-fluoro-6-(1-(6-(1methyl-1H-pyrazol-4-y1)-1H-imidazo[4,5-b]pyrazin-1-yl)ethypquinoline (1), a series of 2-substituted or 3-substituted-6-(1-(1H-[1,2,31triazolo[4,5-b]pyrazin-1-yl)ethyl)quinoline derivatives was rationally designed and evaluated. Most of the 3-substituted derivatives not only exhibited potent activities in both enzymatic and cellular assays, but also were stable in liver microsomes among different species (human, rat and monkey). SAR investigation revealed that introducing of N-methyl-IH-pyrazol-4-yl group at the 3-position of quinoline moiety is beneficial to improve the inhibitory potency, especially in the cellular assays. The influence of fluorine atom at 7-position or 5, 7-position of quinoline moiety and substituents at the 6-position of triazolo[4,5-b]pyrazine core on overall activity is not very significant. Racemate 14, an extremely potent and exquisitely selective c-Met inhibitor, demonstrated favorable pharmacokinetic properties in rats, no significant AO metabolism and effective tumor growth inhibition in c-Met over expressed NSCLC (H1993 cell line) and gastric cancer (SNU-5 cell line) xenograft models. Docking analysis indicated that besides the typical interactions of most selective c-Met inhibitors, the intramolecular halogen bond and additional hydrogen bond interactions with kinase are beneficial to the binding. These results may provide deep insight into potential structural modifications for developing potent c-Met inhibitors. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.03.085