1-((E)-3-(3,4-dihydroxyphenyl)acrylyl)-4-phenylpiperazine

• 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-phenylpiperazine
• 英文别名: (E)-3-(3,4-dihydroxyphenyl)-1-(4-phenylpiperazin-1-yl)prop-2-en-1-one；(E)-3-(3,4-dihydroxy-phenyl)-1-(4-phenylpiperazin-1-yl)-propenone
• 化学式: C₁₉H₂₀N₂O₃
• 分子量: 324.379
• InChiKey: UDDSUIRTIFDYQV-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  64
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-苯基哌嗪 、 (E)-3-(3,4-dihydroxyphenyl)acryloyl chloride 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 1-((E)-3-(3,4-dihydroxyphenyl)acrylyl)-4-phenylpiperazine
  参考文献：
  名称：

  WO2008/26125

  摘要：

  公开号：

文献信息

• Development of Semisynthetic Apoptosis-Inducing Agents Based on Natural Phenolic Acids Scaffold: Design, Synthesis and In-Vitro Biological Evaluation
  作者：Shahira M. Ezzat、Heba El Sayed Teba、Inas G. Shahin、Ahmed M. Hafez、Aliaa M. Kamal、Nora M. Aborehab

  DOI：10.3390/molecules27196724

  日期：——

  A crucial target in drug research is magnifying efficacy and decreasing toxicity. Therefore, using natural active constituents as precursors will enhance both safety and biological activities. Despite having many pharmacological activities, caffeic and ferulic acids showed limited clinical usage due to their poor bioavailability and fast elimination. Therefore, semisynthetic compounds from these two acids were prepared and screened as anticancer agents. In this study, CA and FA showed very potent anticancer activity against Caco-2 cells. Consequently, eighteen derivatives were tested against the same cell line. Four potent candidates were selected for determination of the selectivity index, where compound 10 revealed a high safety margin. Compound 10 represented a new scaffold and showed significant cytotoxic activity against Caco-2. Cell-cycle analysis and evaluation of apoptosis showed that derivatives 10, 7, 11, 15 and 14 showed the highest proportion of cells in a late apoptotic stage.

  药物研究的一个重要目标是提高疗效和降低毒性。因此，使用天然活性成分作为前体将提高安全性和生物活性。尽管咖啡酸和阿魏酸具有多种药理活性，但由于它们的生物利用度低、消除速度快，因此临床应用有限。因此，我们制备了这两种酸的半合成化合物，并将其作为抗癌剂进行筛选。在这项研究中，CA 和 FA 对 Caco-2 细胞显示出非常强的抗癌活性。因此，研究人员针对同一细胞系测试了 18 种衍生物。在确定选择性指数时，选出了四种有效的候选化合物，其中化合物 10 显示出较高的安全系数。化合物 10 代表了一种新的支架，对 Caco-2 细胞具有显著的细胞毒性活性。细胞周期分析和细胞凋亡评估显示，衍生物 10、7、11、15 和 14 中细胞凋亡晚期的比例最高。
• 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.
• WO2008/26125
  申请人：——

  公开号：——

  公开（公告）日：——