4-(3-chloro-4-fluorophenylamino)-6,7-dimethoxy-N-[(2,2,6,6-tetramethyl-1-oxyl)piperidin-4-yl]quinoline-3-carboxamide | 1362021-45-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(3-chloro-4-fluorophenylamino)-6,7-dimethoxy-N-[(2,2,6,6-tetramethyl-1-oxyl)piperidin-4-yl]quinoline-3-carboxamide
• CAS: 1362021-45-1
• 化学式: C₂₇H₃₁ClFN₄O₄
• 分子量: 530.019
• InChiKey: UYERHRWQQVHNFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-(3-Chloro-4-fluoroanilino)-6,7-dimethoxyquinoline-3-carboxylic acid 、 4-氨基-TEMPO 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 以12%的产率得到4-(3-chloro-4-fluorophenylamino)-6,7-dimethoxy-N-[(2,2,6,6-tetramethyl-1-oxyl)piperidin-4-yl]quinoline-3-carboxamide
  参考文献：
  名称：

  Synthesis and biological evaluation of quinazoline and quinoline bearing 2,2,6,6-tetramethylpiperidine-N-oxyl as potential epidermal growth factor receptor(EGFR) tyrosine kinase inhibitors and EPR bio-probe agents

  摘要：

  4-anilinoquinazoline and 4-anilinoquinoline scaffolds bearing a 2,2,6,6-tetramethylpiperidine-N-oxy-1(TEMPO) have been synthesized and evaluated for their ability to inhibit EGFR tyrosine kinase and A431 cell lines. Compared to their corresponding parent compounds, all of the new compounds bearing a TEMPO showed more efficient inhibition for EGFR and A431 cells. Furthermore, we have proved that these molecules bearing a TEMPO can exactly get into A431 cells exerting inhibitory effect that may be used for EPR detecting. In our docking model, quinazolines bearing a TEMPO on either 6- or 3-positions took different linking modes according to EGFR crystal structure. In contrast to their parent compounds, these new TEMPO-derived analogues possessed compatible inhibitory effect that might be useful as potential EGFR inhibitors and as EPR bio-probes. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.021