6-chloro-3-nitro-N-[4-(trifluoromethoxy)phenyl]pyridin-2-amine | 1402088-09-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-chloro-3-nitro-N-[4-(trifluoromethoxy)phenyl]pyridin-2-amine
• CAS: 1402088-09-8
• 化学式: C₁₂H₇ClF₃N₃O₃
• 分子量: 333.654
• InChiKey: NDFFSLCKTVSNMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,6-二氯-3-硝基吡啶 、 对三氟甲氧基苯胺 在 potassium carbonate 作用下， 以 叔丁醇 为溶剂， 反应 24.0h， 以65%的产率得到6-chloro-3-nitro-N-[4-(trifluoromethoxy)phenyl]pyridin-2-amine
  参考文献：
  名称：

  Design and synthesis of diarylamines and diarylethers as cytotoxic antitumor agents

  摘要：

  Based on a shared structural core of diarylamine in several known anticancer drugs as well as a new cytotoxic hit 6-chloro-2-(4-cyanophenyl)amino-3-nitropyridine (7), 30 diarylamines and diarylethers were designed, synthesized, and evaluated for cytotoxic activity against A549, KB, KB-vin, and DU145 human tumor cell lines (HTCL). Four new leads 11e, 12, 13a, and 13b were discovered with GI(50) values ranging from 0.33 to 3.45 mu M. Preliminary SAR results revealed that a diarylamine or diarylether could serve as an active structural core, meta-chloro and ortho-nitro groups on the A-ring (either pyridine or phenyl ring) were necessary and crucial for cytotoxic activity, and the para-substituents on the other phenyl ring (B-ring) were related to inhibitory selectivity for different tumor cells. In an investigation of potential biological targets of the new leads, high thoughput kinase screening discovered that new leads 11e, 12 and 13b especially inhibit Mer tyrosine kinase, a proto-oncogene associated with munerous tumor types, with IC50 values of 2.2-3.0 mu M. Therefore, these findings provide a good starting point to optimize a new class of compounds as potential anticancer agents, particularly targeting Mer tyrosine kinase. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.014