(S)-3-((5S,12S)-5-decyl-12-(methoxymethoxy)-2,4,7,10-tetraoxatetracos-16-en-14-yn-24-yl-8,8,9,9-d4)-5-methylfuran-2(5H)-one | 854375-94-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-3-((5S,12S)-5-decyl-12-(methoxymethoxy)-2,4,7,10-tetraoxatetracos-16-en-14-yn-24-yl-8,8,9,9-d4)-5-methylfuran-2(5H)-one
• CAS: 854375-94-3
• 化学式: C₃₇H₆₄O₈
• 分子量: 640.879
• InChiKey: KUSMOKASXASZKX-BMKHVDAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.08
• 重原子数：
  45.0
• 可旋转键数：
  31.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S)-3-((5S,12S)-5-decyl-12-(methoxymethoxy)-2,4,7,10-tetraoxatetracos-16-en-14-yn-24-yl-8,8,9,9-d4)-5-methylfuran-2(5H)-one 在 盐酸 、 sodium acetate 、 对甲苯磺酰肼 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 生成 AA005-d4
  参考文献：
  名称：

  Synthesis of a tetra-deuterium-labeled derivative of potent and selective anticancer agent AA005

  摘要：

  Annonaceous acetogenins are a series of potent naturally occurring anticancer agents, which act as inhibitors of complex I in mitochondria. AA005, a mimicry of acetogenins, has been found as active as those natural products and to present high selectivities between cancer and normal cells. In order to investigate the further cell-based mechanism induced by AA005, a d(4)-labeled derivative of AA005 (AA005-d(4)) was designed to detect the drug permeation ability into the membranes. In this letter, the synthesis is reported of this deuterium-labeled compound, wherein a ethylene-d(4) glycol unit is incorporated efficiently into the molecule skeleton by simple etherifications. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.123
• 作为产物：
  描述：

  n-nonylidene triphenylphosphorane 在 palladium on activated charcoal 正丁基锂 、 三氟化硼乙醚 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 间氯过氧苯甲酸 、 三氟乙酸酐 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 生成 (S)-3-((5S,12S)-5-decyl-12-(methoxymethoxy)-2,4,7,10-tetraoxatetracos-16-en-14-yn-24-yl-8,8,9,9-d4)-5-methylfuran-2(5H)-one
  参考文献：
  名称：

  Synthesis of a tetra-deuterium-labeled derivative of potent and selective anticancer agent AA005

  摘要：

  Annonaceous acetogenins are a series of potent naturally occurring anticancer agents, which act as inhibitors of complex I in mitochondria. AA005, a mimicry of acetogenins, has been found as active as those natural products and to present high selectivities between cancer and normal cells. In order to investigate the further cell-based mechanism induced by AA005, a d(4)-labeled derivative of AA005 (AA005-d(4)) was designed to detect the drug permeation ability into the membranes. In this letter, the synthesis is reported of this deuterium-labeled compound, wherein a ethylene-d(4) glycol unit is incorporated efficiently into the molecule skeleton by simple etherifications. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.123