N-(4-(4-((4-acetylphenyl)amino)-5-cyanopyridin-3-yl)phenyl)-4-(dimethylamino)but-2-enamide | 1436405-68-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(4-(4-((4-acetylphenyl)amino)-5-cyanopyridin-3-yl)phenyl)-4-(dimethylamino)but-2-enamide
• 英文别名: N-[4-[4-(4-acetylanilino)-5-cyanopyridin-3-yl]phenyl]-4-(dimethylamino)but-2-enamide
• CAS: 1436405-68-3
• 化学式: C₂₆H₂₅N₅O₂
• 分子量: 439.517
• InChiKey: IBFXEGXEBATVDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  98.12
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2-(4-硝基苯基)乙酰氯 在 盐酸 、 草酰氯 、 水 、 sodium ethanolate 、 吡啶盐酸盐 、 铁粉 、 氯化铵 、 N,N-二甲基甲酰胺 、 lithium chloride 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 水 、 二甲基亚砜 、 甲苯 为溶剂， 反应 24.5h， 生成 N-(4-(4-((4-acetylphenyl)amino)-5-cyanopyridin-3-yl)phenyl)-4-(dimethylamino)but-2-enamide
  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.