(E)-N-(3-(2,4-dichlorophenyl)-2-(4-methoxybenzoyl)allyl)-N-methylbenzamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-N-(3-(2,4-dichlorophenyl)-2-(4-methoxybenzoyl)allyl)-N-methylbenzamide
• 英文别名: N-[(E)-3-(2,4-dichlorophenyl)-2-(4-methoxybenzoyl)prop-2-enyl]-N-methylbenzamide
• 化学式: C₂₅H₂₁Cl₂NO₃
• 分子量: 454.353
• InChiKey: NDCLMEGKYHSKSC-XSFVSMFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(3-(4-methoxyphenyl)prop-2-yn-1-yl)-N-methylbenzamide 、 2,4-二氯苯甲醛 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以51%的产率得到(E)-N-(3-(2,4-dichlorophenyl)-2-(4-methoxybenzoyl)allyl)-N-methylbenzamide
  参考文献：
  名称：

  Synthesis and antiproliferative activity of α-branched α,β-unsaturated ketones in human hematological and solid cancer cell lines

  摘要：

  A series of alpha-branched alpha,beta-unsaturated ketones were prepared via boron trifluoride etherate mediated reaction between arylalkynes and carboxaldehydes. The evaluation of the antiproliferative activity over hematological (NB4) and solid cancer (A549, MCF-7) cell lines provided a structure-activity relationship. 5-Parameter QSAR equations were built which were able to explain 80%-92% of the variance in activity. The resulting selective lead compound showed IC50 value 0.6 mu M against the hematological cell line and did not cause apoptosis, but blocked cell cycle in G0/G1. Moreover, it was demonstrated that this compound enhances and accelerates retinoic acid induced granulocytic differentiation. (C) 2015 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2015.05.012