(4E)-1-(dimethylamino)-5-(4-methoxyphenyl)penta-1,4-dien-3-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4E)-1-(dimethylamino)-5-(4-methoxyphenyl)penta-1,4-dien-3-one
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: CBUFWNOYKAVVIK-UFTYFRIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4E)-1-(dimethylamino)-5-(4-methoxyphenyl)penta-1,4-dien-3-one 在 劳森试剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  交叉共轭烯胺酮的环加成反应

  摘要：

  详细研究了交叉共轭烯胺1和9与乙炔二羧酸二甲酯（DMAD）和乙烯酮的环加成反应。该反应提供各种吡喃的（4，11），吡喃-2-酮14和吡咯-3-亚基8个具有大的药理学和药用意义衍生物。此外，已经基于在气相中对中间体5进行的分子动力学（MD）模拟，解释了产物8相对于7的优选形成。烯胺酮的合成潜力9通过用Lawesson试剂（LR）处理它们，并用一些丙烯酸酯17捕获原位产生的烯胺硫酮16，导致形成了硫吡喃衍生物19，从而进一步探索了硫丹。据我们所知，这是首次在环加成反应中使用交叉共轭烯氨基硫酮16的报道。

  DOI：

  10.1016/j.tet.2009.08.038
• 作为产物：
  描述：

  N,N-二甲基甲酰胺二甲基缩醛 、 反-4-(4-甲氧苯基)-3-丁烯-2-酮 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (4E)-1-(dimethylamino)-5-(4-methoxyphenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  3-Acyl-5-hydroxybenzofuran derivatives as potential anti-estrogen breast cancer agents: A combined experimental and theoretical investigation

  摘要：

  We first report the application of 3-acyl-5-hydroxybenzofurans as a scaffold to develop potential drugs for breast cancer. Seven novel derivative compounds were synthesized by using a microwave-assisted synthesis method. Those compounds exhibited different antiproliferation against human breast cancer MCF-7 cells, with the best activity of IC50=43.08 mu M for compound 1. A Quantum Mechanics Polarized Ligand Docking (QPLD) study was carried out to investigate the binding interactions between these compounds and estrogen receptor alpha (ER alpha). The simulation results showed that the trend of receptor-ligand binding interactions was same as that of their antiproliferative activities. A detailed analysis indicated that compound 1 possesses the highest Van der Waals and hydrogen bond interactions compared to the other six compounds and better inhibitors are achievable by enhancing the hydrogen bond interactions. Based on these results, we addressed that 3-acyl-5-hydroxybenzofuran is an attractive scaffold for designing drugs against breast cancer. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.022

文献信息

• 3-Acyl-5-hydroxybenzofuran derivatives as potential anti-estrogen breast cancer agents: A combined experimental and theoretical investigation
  作者：Xiao-Yan Li、Bi-Feng He、Hua-Jun Luo、Nian-Yu Huang、Wei-Qiao Deng

  DOI：10.1016/j.bmcl.2013.06.022

  日期：2013.8

  We first report the application of 3-acyl-5-hydroxybenzofurans as a scaffold to develop potential drugs for breast cancer. Seven novel derivative compounds were synthesized by using a microwave-assisted synthesis method. Those compounds exhibited different antiproliferation against human breast cancer MCF-7 cells, with the best activity of IC50=43.08 mu M for compound 1. A Quantum Mechanics Polarized Ligand Docking (QPLD) study was carried out to investigate the binding interactions between these compounds and estrogen receptor alpha (ER alpha). The simulation results showed that the trend of receptor-ligand binding interactions was same as that of their antiproliferative activities. A detailed analysis indicated that compound 1 possesses the highest Van der Waals and hydrogen bond interactions compared to the other six compounds and better inhibitors are achievable by enhancing the hydrogen bond interactions. Based on these results, we addressed that 3-acyl-5-hydroxybenzofuran is an attractive scaffold for designing drugs against breast cancer. (C) 2013 Elsevier Ltd. All rights reserved.
• Cycloaddition reactions of cross-conjugated enaminones
  作者：Parvesh Singh、Parul Sharma、Krishna Bisetty、Mohinder P. Mahajan

  DOI：10.1016/j.tet.2009.08.038

  日期：2009.10

  the intermediate 5 in the gas phase. The synthetic potential of enaminones 9 has further been explored by treating them with Lawesson's reagent (LR) and trapping the in situ generated enaminothiones 16 with some acrylates 17 leading to the formation of thiopyran derivatives 19. To the best of our knowledge, this is the first report in which cross-conjugated enaminothiones 16 have been utilized in cycloaddition

  详细研究了交叉共轭烯胺1和9与乙炔二羧酸二甲酯（DMAD）和乙烯酮的环加成反应。该反应提供各种吡喃的（4，11），吡喃-2-酮14和吡咯-3-亚基8个具有大的药理学和药用意义衍生物。此外，已经基于在气相中对中间体5进行的分子动力学（MD）模拟，解释了产物8相对于7的优选形成。烯胺酮的合成潜力9通过用Lawesson试剂（LR）处理它们，并用一些丙烯酸酯17捕获原位产生的烯胺硫酮16，导致形成了硫吡喃衍生物19，从而进一步探索了硫丹。据我们所知，这是首次在环加成反应中使用交叉共轭烯氨基硫酮16的报道。