1-((E)-3-(3,4-dihydroxyphenyl)acrylyl)-4-(4-methoxyphenyl)piperazine | 1621088-31-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-((E)-3-(3,4-dihydroxyphenyl)acrylyl)-4-(4-methoxyphenyl)piperazine
• 英文别名: (E)-3-(3,4-dihydroxyphenyl)-1-[4-(4-methoxyphenyl)piperazin-1-yl]prop-2-en-1-one
• CAS: 1621088-31-0
• 化学式: C₂₀H₂₂N₂O₄
• 分子量: 354.406
• InChiKey: DUXGMVIRWLIQCU-YCRREMRBSA-N

物化性质

• 熔点：
  177-179 °C
• 沸点：
  643.677±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.295±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(4-甲氧基苯基)哌嗪 、 TRANS-咖啡酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到1-((E)-3-(3,4-dihydroxyphenyl)acrylyl)-4-(4-methoxyphenyl)piperazine
  参考文献：
  名称：

  Design, synthesis and biological evaluation of (E)-3-(3,4-dihydroxyphenyl)acrylylpiperazine derivatives as a new class of tubulin polymerization inhibitors

  摘要：

  A series of novel (E)-3-(3,4-dihydroxyphenyl)acrylylpiperazine derivatives had been synthesized and evaluated their biological activities as potential tubulin polymerization inhibitors. Among these compounds, compound 3q exhibited potent antiproliferative activities against three cancer cell lines in vitro, and antitubulin polymerization activity with IC₅₀ of 0.92 μM, which was superior to that of colchicine (IC₅₀=1.34 μM). Docking simulation was performed to insert compound 3q into the crystal structure of tubulin at colchicine binding site to determine the probable binding model. These results suggested that compound 3q may be a promising antitubulin agent for the potential treatment of cancer.

  DOI：

  10.1016/j.bmc.2014.05.029

文献信息

• Design, synthesis and biological evaluation of (E)-3-(3,4-dihydroxyphenyl)acrylylpiperazine derivatives as a new class of tubulin polymerization inhibitors
  作者：Yong Yin、Fang Qiao、Lu-Yi Jiang、She-Feng Wang、Shao Sha、Xun Wu、Peng-Cheng Lv、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2014.05.029

  日期：2014.8

  A series of novel (E)-3-(3,4-dihydroxyphenyl)acrylylpiperazine derivatives had been synthesized and evaluated their biological activities as potential tubulin polymerization inhibitors. Among these compounds, compound 3q exhibited potent antiproliferative activities against three cancer cell lines in vitro, and antitubulin polymerization activity with IC₅₀ of 0.92 μM, which was superior to that of colchicine (IC₅₀=1.34 μM). Docking simulation was performed to insert compound 3q into the crystal structure of tubulin at colchicine binding site to determine the probable binding model. These results suggested that compound 3q may be a promising antitubulin agent for the potential treatment of cancer.