(5S,12S)-5-(14-azidotetradecyl)-12-decyl-2,4,7,10,13,15-hexaoxahexadecane | 1616683-39-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (5S,12S)-5-(14-azidotetradecyl)-12-decyl-2,4,7,10,13,15-hexaoxahexadecane
• CAS: 1616683-39-6
• 化学式: C₃₄H₆₉N₃O₆
• 分子量: 615.938
• InChiKey: LRBXIDGSXRHAID-HEVIKAOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.91
• 重原子数：
  43.0
• 可旋转键数：
  37.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  104.14
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (5S,12S)-5-(14-azidotetradecyl)-12-decyl-2,4,7,10,13,15-hexaoxahexadecane 在 盐酸 、 copper(ll) sulfate pentahydrate 、 甲基磺酰氯 、 sodium ascorbate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 (S)-1-(2-(((S)-2-hydroxydodecyl)oxy)ethoxy)-16-(4-methyl-1H-1,2,3-triazol-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
• 作为产物：
  描述：

  在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 sodium azide 、 p-toluenesulfonylhydrazide 、 sodium acetate 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.83h， 生成 (5S,12S)-5-(14-azidotetradecyl)-12-decyl-2,4,7,10,13,15-hexaoxahexadecane
  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