2-amino-N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-5-(4-(dimethylamino)but-2-enamido)-4-ethoxybenzamide | 1436405-77-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-amino-N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-5-(4-(dimethylamino)but-2-enamido)-4-ethoxybenzamide
• 英文别名: 2-amino-N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-5-[4-(dimethylamino)but-2-enoylamino]-4-ethoxybenzamide
• CAS: 1436405-77-4
• 化学式: C₂₈H₃₀ClFN₄O₄
• 分子量: 541.022
• InChiKey: DTYRZJIJCBDMSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  105.92
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 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 、 calcium chloride 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 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

文献信息

• Design, synthesis and biological evaluation of novel pyrimidine, 3-cyanopyridine and m-amino-N-phenylbenzamide based monocyclic EGFR tyrosine kinase inhibitors
  作者：Yongjun Mao、Wenxiu Zhu、Xiaoguang Kong、Zhen Wang、Hua Xie、Jian Ding、Nicholas Kenneth Terrett、Jingkang Shen、Jingshan Shen

  DOI：10.1016/j.bmc.2013.03.053

  日期：2013.6

  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.