N-(3-chloro-4-fluorophenyl)-4-ethoxy-5-(4-((4-methylpiperazin-1-yl)methyl)benzamido)-2-nitrobenzamide | 1436405-83-2

• 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-(3-chloro-4-fluorophenyl)-4-ethoxy-5-(4-((4-methylpiperazin-1-yl)methyl)benzamido)-2-nitrobenzamide
• 英文别名: N-(3-chloro-4-fluorophenyl)-4-ethoxy-5-[[4-[(4-methylpiperazin-1-yl)methyl]benzoyl]amino]-2-nitrobenzamide
• CAS: 1436405-83-2
• 化学式: C₂₈H₂₉ClFN₅O₅
• 分子量: 570.02
• InChiKey: LXSXCIYVAJUOHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(3-chloro-4-fluorophenyl)-4-ethoxy-5-(4-((4-methylpiperazin-1-yl)methyl)benzamido)-2-nitrobenzamide 在 calcium chloride 、 锌 作用下， 以 乙醇 、 水 为溶剂， 反应 10.0h， 以85%的产率得到2-amino-N-(3-chloro-4-fluorophenyl)-4-ethoxy-5-(4-((4-methylpiperazin-1-yl)methyl)benzamido)benzamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel pyrimidine, 3-cyanopyridine and m-amino-N-phenylbenzamide based monocyclic EGFR tyrosine kinase inhibitors

  摘要：

  36 new compounds with the typical skeleton of 4-anilino-5-vinyl/ethynyl pyrimidine, 4-anilino-3-cyano-5-vinyl/ethynyl/phenyl pyridine, and m-amino-N-phenylbenzamide, are designed, synthesized and selectively tested on EGFR, ErbB-2 kinases, and A-549, HL60 cells growth inhibition. Results from the bioactivity and chemical structures yield preliminary structure-activity relationships (SARs). The most potent 5-ethynylpyrimidine derivative 20a has an IC50 value of 45 nM to EGFR kinase. Several compounds of other series also show IC50 values <1 mu M for EGFR and <5 mu M for A-549 and HL60 cells growth inhibition. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.03.053
• 作为产物：
  描述：

  3-acetamido-4-hydroxybenzoic acid 在 吡啶 、 氯化亚砜 、 硝酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 N-(3-chloro-4-fluorophenyl)-4-ethoxy-5-(4-((4-methylpiperazin-1-yl)methyl)benzamido)-2-nitrobenzamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel pyrimidine, 3-cyanopyridine and m-amino-N-phenylbenzamide based monocyclic EGFR tyrosine kinase inhibitors

  摘要：

  36 new compounds with the typical skeleton of 4-anilino-5-vinyl/ethynyl pyrimidine, 4-anilino-3-cyano-5-vinyl/ethynyl/phenyl pyridine, and m-amino-N-phenylbenzamide, are designed, synthesized and selectively tested on EGFR, ErbB-2 kinases, and A-549, HL60 cells growth inhibition. Results from the bioactivity and chemical structures yield preliminary structure-activity relationships (SARs). The most potent 5-ethynylpyrimidine derivative 20a has an IC50 value of 45 nM to EGFR kinase. Several compounds of other series also show IC50 values <1 mu M for EGFR and <5 mu M for A-549 and HL60 cells growth inhibition. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.03.053