methyl (Z)-9-hydroxyoctadec-12-en-10-ynoate | 1225215-10-0

• 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: methyl (Z)-9-hydroxyoctadec-12-en-10-ynoate
• CAS: 1225215-10-0
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: QHWJHOYCIHXURZ-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  22.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl (Z)-9-hydroxyoctadec-12-en-10-ynoate 在 1% Pd/C 、 氢气 作用下， 以 甲醇 为溶剂， 以78%的产率得到9-羟基十八烷酸甲酯
  参考文献：
  名称：

  Unprecedented NES non-antagonistic inhibitor for nuclear export of Rev from Sida cordifolia

  摘要：

  Bioassay-guided separation from the MeOH extract of the South American medicinal plant Sida cordifolia resulted in isolation of (10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid (1) as an unprecedented NES non-antagonistic inhibitor for nuclear export of Rev. This mechanism of action was established by competitive experiment by the biotinylated probe derived from leptomycin B, the known NES antagonistic inhibitor. Additionally, structure-activity relationship analysis by use of the synthesized analogs clarified cooperation of several functionalities in the Rev-export inhibitory activity of 1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.165
• 作为产物：
  描述：

  (Z)-1-iodohept-1-ene 、 methyl 9-hydroxy-undec-10-ynoate 在 哌啶 、 双(乙腈)氯化钯(II) 、 copper(l) iodide 作用下， 以62%的产率得到methyl (Z)-9-hydroxyoctadec-12-en-10-ynoate
  参考文献：
  名称：

  Unprecedented NES non-antagonistic inhibitor for nuclear export of Rev from Sida cordifolia

  摘要：

  Bioassay-guided separation from the MeOH extract of the South American medicinal plant Sida cordifolia resulted in isolation of (10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid (1) as an unprecedented NES non-antagonistic inhibitor for nuclear export of Rev. This mechanism of action was established by competitive experiment by the biotinylated probe derived from leptomycin B, the known NES antagonistic inhibitor. Additionally, structure-activity relationship analysis by use of the synthesized analogs clarified cooperation of several functionalities in the Rev-export inhibitory activity of 1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.165