(1S,2R,4aR,5R,8R,8aR)-2-acetoxy-8a-hydroxy-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl (2S,3aR,8aS)-1-acetyl-3a-hydroxy-8-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate | 1448513-68-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (1S,2R,4aR,5R,8R,8aR)-2-acetoxy-8a-hydroxy-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl (2S,3aR,8aS)-1-acetyl-3a-hydroxy-8-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate
• CAS: 1448513-68-5
• 化学式: C₃₁H₄₀N₂O₇
• 分子量: 552.668
• InChiKey: AVUHXBQICAJWQT-UUZFKWNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  40.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  116.61
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  乙酸酐 、 啶南平A 在 吡啶 作用下， 反应 1.0h， 以3.4 mg的产率得到(1S,2R,4aR,5R,8R,8aR)-2-acetoxy-8a-hydroxy-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl (2S,3aR,8aS)-1-acetyl-3a-hydroxy-8-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate
  参考文献：
  名称：

  Fischerindoline, a pyrroloindole sesquiterpenoid isolated from Neosartorya pseudofischeri, with in vitro growth inhibitory activity in human cancer cell lines

  摘要：

  A novel pyrroloindole terpenoid, named fischerindoline (1), was isolated together with the known metabolites eurochevalierine, pyripyropenes A and E, sequiterpene, gliotoxin, and bis(dethio)bis(methylthio)gliotoxin from solid and liquid cultures of Neosartoiya pseudofischeri. Fischerindoline was characterized as 3a-hydroxy-8-methyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid, 2-acetoxy-8a-hydroxy-5-isopropenyl-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl ester by spectroscopic and chemical methods. Fischerindoline displays in vitro growth inhibitory activity in six human and mouse cancer cell lines. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.031