(2E)-N-(4-isopropylphenyl)cinnamamide | 1384289-54-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (2E)-N-(4-isopropylphenyl)cinnamamide
• 英文别名: (E)-3-phenyl-N-(4-propan-2-ylphenyl)prop-2-enamide
• CAS: 1384289-54-6
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: SRJUSGJYCYFWDF-MDWZMJQESA-N

物化性质

• 沸点：
  450.2±38.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  肉桂酸 在 4-二甲氨基吡啶 、 氯化亚砜 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2E)-N-(4-isopropylphenyl)cinnamamide
  参考文献：
  名称：

  Synthesis, structure, and biological assay of cinnamic amides as potential EGFR kinase inhibitors

  摘要：

  A series of derivatives of cinnamic amide (compounds 2a-2v) were synthesized and evaluated for antiproliferative activities against the human breast cancer cell line MCF-7- and EGFR-inhibitory activities. The structures of compounds 2b and 2i were determined by single-crystal X-ray diffraction analysis. Compounds 2f and 2j showed moderate EGFR inhibitory activity with IC50 values of 5.16 and 7.37 mu M, respectively. Docking simulation of compound 2f was carried out to illustrate the binding mode of the molecule into the EGFR active site. Structure-activity relationship analysis found that the N-phenyl rings are required for enhancing the activities.

  DOI：

  10.1007/s00044-012-0093-z

文献信息

• Synthesis, structure, and biological assay of cinnamic amides as potential EGFR kinase inhibitors
  作者：Mao Zhang、Xiang Lu、Hong-Jia Zhang、Na Li、Yu Xiao、Hai-Liang Zhu、Yong-Hao Ye

  DOI：10.1007/s00044-012-0093-z

  日期：2013.2

  A series of derivatives of cinnamic amide (compounds 2a-2v) were synthesized and evaluated for antiproliferative activities against the human breast cancer cell line MCF-7- and EGFR-inhibitory activities. The structures of compounds 2b and 2i were determined by single-crystal X-ray diffraction analysis. Compounds 2f and 2j showed moderate EGFR inhibitory activity with IC50 values of 5.16 and 7.37 mu M, respectively. Docking simulation of compound 2f was carried out to illustrate the binding mode of the molecule into the EGFR active site. Structure-activity relationship analysis found that the N-phenyl rings are required for enhancing the activities.