红毒扁豆碱 | 18455-27-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 红毒扁豆碱
• 英文名称: rubreserine
• 英文别名: (3aS)-1,3a,8-trimethyl-(3ar,8ac)-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-5,6-dione；(3aS)-6-Hydroxy-1,3a,8-trimethyl-5-oxo-(3ar,8ac)-1,2,3,3a,5,8a-hexahydro-pyrrolo[2,3-b]indolium-betain；(3aS)-1,3a,8-Trimethyl-(3ar,8ac)-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5,6-dion；(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-6,7-dione
• CAS: 18455-27-1
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: HOQNKCYZDSDWJL-OLZOCXBDSA-N

物化性质

• 熔点：
  152 °C
• 沸点：
  359.5±42.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  (-)-氧化毒扁豆碱富马酸盐 在 氧气 、 碳酸氢钠 作用下， 以 氯仿 为溶剂， 以21%的产率得到红毒扁豆碱
  参考文献：
  名称：

  Syntheses and Anticholinesterase Activities of (3aS)-N,N⁸-Bisnorphenserine, (3aS)-N¹,N⁸-Bisnorphysostigmine, Their Antipodal Isomers, and Other Potential Metabolites of Phenserine

  摘要：

  Hydrolysis of the carbamate side chains in phenserine [(-)1] and physostigmine [(-)2] yields the metabolite (-)-eseroline (3), and the red dye rubreserine (4) on air oxidation of the former compound. Both compounds lacked anticholinesterase activity in concentrations up to 30 mM, which would be unachievable in vivo. A second group of potential metabolites of 1 and 2 are the N-1,N-8-bisnorcarbamates (-)9 and (-)10, prepared from (3aS)-N-8-benzylnoresermethole (-)12 by the carbinolamine route. These entirely novel compounds proved to be highly potent inhibitors of acetylcholinesterase [(-)9] and of acetyl- and butyrylcholinesterase (AChE and BChE) [(-)10], respectively. To elucidate further the structure/anticholinesterase activity relationship of the described compounds, the antipodal isomers (3aR)-N-1,N-8-bisnorcarbamates (+)9 and (+)10 were likewise synthesized from (3aR)-N-8-benzylnoresermethole (+)12 and assessed. The compounds possessed moderate but less potent anticholinesterase activity, with the same selectivity as their 3aS enantiomers. Finally, the anticholinesterase activities of intermediates N-1,N-8-bisnorbenzylcarbamates (-)18, (-)19, (+)18, and (+)19, also novel compounds, were additionally measured. The 3aS enantiomers proved to be potent and selective inhibitors of BChE, particularly (-)19, whereas the antipodal isomers lacked activity.

  DOI：

  10.1021/jm9800494