(S)-1-(2-(((S)-2-hydroxydodecyl)oxy)ethoxy)-16-(piperidin-1-yl)hexadecan-2-ol | 1616683-27-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (S)-1-(2-(((S)-2-hydroxydodecyl)oxy)ethoxy)-16-(piperidin-1-yl)hexadecan-2-ol
• 英文别名: (2S)-1-[2-[(2S)-2-hydroxydodecoxy]ethoxy]-16-piperidin-1-ylhexadecan-2-ol
• CAS: 1616683-27-2
• 化学式: C₃₅H₇₁NO₄
• 分子量: 569.953
• InChiKey: ZNQGIMRXUNKBGO-PXLJZGITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  40
• 可旋转键数：
  31
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  10-烯酸甲酯 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 p-toluenesulfonylhydrazide 、 sodium acetate 、 甲基磺酰氯 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 26.83h， 生成 (S)-1-(2-(((S)-2-hydroxydodecyl)oxy)ethoxy)-16-(piperidin-1-yl)hexadecan-2-ol
  参考文献：
  名称：

  New cytotoxic annonaceous acetogenin mimetics having a nitrogen-heterocyclic terminal and their application to cell imaging

  摘要：

  A terminal unsaturated lactone or its equivalent is commonly believed to be essential for the cytotoxicity of natural annonaceous acetogenins and their artificial mimetics. In this work, we discovered a series of new cytotoxic ethylene glycol ether-containing mimetics, in which a variety of simple aliphatic nitrogen-heterocycles were introduced to replace the lactone terminal of AA005 (1), a representative bioactive polyether mimic identified from our previous research, for the first time. Among these, mimic 4 bearing a terminal piperazine was found to be the most potent compound against the proliferation of three cancer cells. Based on our new findings, a fluorescent probe 7 was also developed and successfully applied to the imaging of cancer cells. This work provides a new strategy for developing simpler cytotoxic mimetics of natural annonaceous acetogenins and molecular tools for biological imaging. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.047

文献信息

• New cytotoxic annonaceous acetogenin mimetics having a nitrogen-heterocyclic terminal and their application to cell imaging
  作者：Yi-Jie Chen、Sheng Jin、Jie Xi、Zhu-Jun Yao

  DOI：10.1016/j.tet.2014.05.047

  日期：2014.8

  A terminal unsaturated lactone or its equivalent is commonly believed to be essential for the cytotoxicity of natural annonaceous acetogenins and their artificial mimetics. In this work, we discovered a series of new cytotoxic ethylene glycol ether-containing mimetics, in which a variety of simple aliphatic nitrogen-heterocycles were introduced to replace the lactone terminal of AA005 (1), a representative bioactive polyether mimic identified from our previous research, for the first time. Among these, mimic 4 bearing a terminal piperazine was found to be the most potent compound against the proliferation of three cancer cells. Based on our new findings, a fluorescent probe 7 was also developed and successfully applied to the imaging of cancer cells. This work provides a new strategy for developing simpler cytotoxic mimetics of natural annonaceous acetogenins and molecular tools for biological imaging. (C) 2014 Elsevier Ltd. All rights reserved.