(E)-1-(5-hydroxy-6-methoxybenzofuran-3-yl)-3-phenylprop-2-en-1-one | 1448799-01-6

• 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: (E)-1-(5-hydroxy-6-methoxybenzofuran-3-yl)-3-phenylprop-2-en-1-one
• 英文别名: (E)-1-(5-hydroxy-6-methoxy-1-benzofuran-3-yl)-3-phenylprop-2-en-1-one
• CAS: 1448799-01-6
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: YJQPWQAVHRGPKE-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苄叉丙酮 在 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (E)-1-(5-hydroxy-6-methoxybenzofuran-3-yl)-3-phenylprop-2-en-1-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.