N-Cyanmethyl-3-nitranilin | 4718-05-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-Cyanmethyl-3-nitranilin
• 英文别名: m-Nitroanilinoacetonitril；2-(3-Nitroanilino)acetonitrile
• CAS: 4718-05-2
• 化学式: C₈H₇N₃O₂
• 分子量: 177.162
• InChiKey: WMPRSRMAKSWJGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  81.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Cyanmethyl-3-nitranilin 在 三乙胺盐酸盐 、 铁粉 、 氯化铵 、 三氟乙酸 作用下， 以 甲醇 、 水 、 甲苯 、 仲丁醇 为溶剂， 反应 15.75h， 生成
  参考文献：
  名称：

  Identification of 2(1H)-pyrimidinones as potential EGFR T790M inhibitors for the treatment of gefitinib-resistant non-small cell lung cancer

  摘要：

  A new class of 2(1H)-pyrimidinone derivatives was identified as potential EGFR T790M inhibitors against TKI-resistant NSCLC. These novel compounds inhibited the EGFR T790M kinase activity at concentrations in the range of 85.3 to 519.9 nM. In particular, compound 7e exhibited the strongest activity against both EGFR(WT) (IC50 = 96.9 nM) and EGFR(T790M) (IC50 = 85.3 nM) kinases in the cells. Compared with inhibitor 7e, compound 7b displayed enhanced antiproliferative activity against gefitinib-resistant H1975 cells harboring the EGFR T790M mutation. In addition, compound 7b also has low toxicity against the normal human liver cells LO2, with an IC50 of 11.1 mu M. Moreover, both the AO/EB and DAPI staining assays also demonstrated the inhibitory efficacy of 7b against the resistant H1975 cells. This contribution provides a new scaffold 2(1H)-pyrimidinone as potential EGFR T790M inhibitor against drug-resistant NSCLC.

  DOI：

  10.1016/j.bioorg.2019.102994
• 作为产物：
  描述：

  间硝基苯胺 、 乙腈 在 potassium carbonate 、 potassium iodide 作用下， 反应 48.0h， 以54%的产率得到N-Cyanmethyl-3-nitranilin
  参考文献：
  名称：

  Identification of 2(1H)-pyrimidinones as potential EGFR T790M inhibitors for the treatment of gefitinib-resistant non-small cell lung cancer

  摘要：

  A new class of 2(1H)-pyrimidinone derivatives was identified as potential EGFR T790M inhibitors against TKI-resistant NSCLC. These novel compounds inhibited the EGFR T790M kinase activity at concentrations in the range of 85.3 to 519.9 nM. In particular, compound 7e exhibited the strongest activity against both EGFR(WT) (IC50 = 96.9 nM) and EGFR(T790M) (IC50 = 85.3 nM) kinases in the cells. Compared with inhibitor 7e, compound 7b displayed enhanced antiproliferative activity against gefitinib-resistant H1975 cells harboring the EGFR T790M mutation. In addition, compound 7b also has low toxicity against the normal human liver cells LO2, with an IC50 of 11.1 mu M. Moreover, both the AO/EB and DAPI staining assays also demonstrated the inhibitory efficacy of 7b against the resistant H1975 cells. This contribution provides a new scaffold 2(1H)-pyrimidinone as potential EGFR T790M inhibitor against drug-resistant NSCLC.

  DOI：

  10.1016/j.bioorg.2019.102994