N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-5-(4-(dimethylamino)but-2-enamido)-4-ethoxy-2-nitrobenzamide | 1436405-76-3

• 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-((3-fluorobenzyl)oxy)phenyl)-5-(4-(dimethylamino)but-2-enamido)-4-ethoxy-2-nitrobenzamide
• 英文别名: N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-5-[4-(dimethylamino)but-2-enoylamino]-4-ethoxy-2-nitrobenzamide
• CAS: 1436405-76-3
• 化学式: C₂₈H₂₈ClFN₄O₆
• 分子量: 571.005
• InChiKey: KYITYRICHGVEAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  40.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  123.04
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-5-(4-(dimethylamino)but-2-enamido)-4-ethoxy-2-nitrobenzamide 在 calcium chloride 、 锌 作用下， 以 乙醇 、 水 为溶剂， 反应 10.0h， 以87%的产率得到2-amino-N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-5-(4-(dimethylamino)but-2-enamido)-4-ethoxybenzamide
  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 氯化亚砜 、 草酰氯 、 硝酸 、 potassium carbonate 、 溶剂黄146 、 N,N-二甲基甲酰胺 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 16.0h， 生成 N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-5-(4-(dimethylamino)but-2-enamido)-4-ethoxy-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