15,24,28-tri-O-(Nα-Boc-Nω-Z-lysyl)squamocin | 855999-10-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 15,24,28-tri-O-(Nα-Boc-Nω-Z-lysyl)squamocin
• CAS: 855999-10-9
• 化学式: C₉₄H₁₄₄N₆O₂₂
• 分子量: 1710.2
• InChiKey: NKRYACWRJIVGRI-HEJBJBPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.48
• 重原子数：
  122.0
• 可旋转键数：
  55.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  353.64
• 氢给体数：
  6.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  15,24,28-tri-O-(Nα-Boc-Nω-Z-lysyl)squamocin 在 吡啶 、 氢氟酸 作用下， 以 苯甲醚 为溶剂， 反应 5.0h， 以57%的产率得到15,24,28-tri-O-(Nω-Z-lysyl)squamocin trihydrofluoride
  参考文献：
  名称：

  Semisynthesis and biological activity of aminoacyl triesters of squamocin, an annonaceous acetogenin

  摘要：

  A number of aminoacyl triesters of squamocin 1, a cytotoxic acetogenin isolated from the seeds of Annona reticulata, have been synthesized in two to three steps from protected (L)-aminoacids and squamocin 1 using standard coupling/deprotection procedures. These semisynthetic analogs were tested on submitochondrial particles (SMP) for their complex I inhibitory activities, and against KB 3-1 cells in vitro. All triesters derivatives exhibited a complete extinction of activity at the enzymatic level, correlated to a reduced though modulated cytotoxicity in comparison with squamocin 1. This activity can apparently be considered as a function of the amphipathy of the analogs, the more amphiphilic ones being the more cytotoxic. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.029
• 作为产物：
  描述：

  N-Boc-N'-Cbz-L-赖氨酸 、 (5S)-3-[(13R)-13-[(2R,5R)-5-[(2R,5R)-5-[(1S,5S)-1,5-二羟基十一烷基]四氢呋喃-2-基]四氢呋喃-2-基]-13-羟基十三烷基]-5-甲基-5H-呋喃-2-酮 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 15.0h， 以83%的产率得到15,24,28-tri-O-(Nα-Boc-Nω-Z-lysyl)squamocin
  参考文献：
  名称：

  Semisynthesis and biological activity of aminoacyl triesters of squamocin, an annonaceous acetogenin

  摘要：

  A number of aminoacyl triesters of squamocin 1, a cytotoxic acetogenin isolated from the seeds of Annona reticulata, have been synthesized in two to three steps from protected (L)-aminoacids and squamocin 1 using standard coupling/deprotection procedures. These semisynthetic analogs were tested on submitochondrial particles (SMP) for their complex I inhibitory activities, and against KB 3-1 cells in vitro. All triesters derivatives exhibited a complete extinction of activity at the enzymatic level, correlated to a reduced though modulated cytotoxicity in comparison with squamocin 1. This activity can apparently be considered as a function of the amphipathy of the analogs, the more amphiphilic ones being the more cytotoxic. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.029