5-amino-N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-2-methylbenzamide | 1436405-94-5

• 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: 5-amino-N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-2-methylbenzamide
• CAS: 1436405-94-5
• 化学式: C₂₁H₁₈ClFN₂O₂
• 分子量: 384.838
• InChiKey: GDGLTTRSRAVWIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  64.35
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(dimethylamino)but-2-enoic acid hydrobromide 、 5-amino-N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-2-methylbenzamide 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 反应 4.5h， 以25%的产率得到N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-5-(4-(dimethylamino)but-2-enamido)-2-methylbenzamide
  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：

  N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-2-methyl-5-nitrobenzamide 在 盐酸 、 铁粉 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 反应 5.0h， 以98%的产率得到5-amino-N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-2-methylbenzamide
  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