(5S,12S)-5-decyl-12-(methoxymethoxy)-2,4,7,10-tetraoxahexacosan-26-yl methanesulfonate | 1616683-35-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (5S,12S)-5-decyl-12-(methoxymethoxy)-2,4,7,10-tetraoxahexacosan-26-yl methanesulfonate
• CAS: 1616683-35-2
• 化学式: C₃₅H₇₂O₉S
• 分子量: 669.017
• InChiKey: OTHOAXGZSRJSEE-PXLJZGITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.58
• 重原子数：
  45.0
• 可旋转键数：
  38.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  98.75
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (5S,12S)-5-decyl-12-(methoxymethoxy)-2,4,7,10-tetraoxahexacosan-26-yl methanesulfonate 在 sodium tetrahydroborate 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 、 水 为溶剂， 反应 7.0h， 以91%的产率得到(S)-1-(2-(((S)-2-hydroxydodecyl)oxy)ethoxy)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：

  methyl (5S,12S)-5-decyl-12-(methoxymethoxy)-2,4,7,10-tetraoxahexacosan-26-oate 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (5S,12S)-5-decyl-12-(methoxymethoxy)-2,4,7,10-tetraoxahexacosan-26-yl methanesulfonate
  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