ethyl carbamic acid 1,8-diacetyl-3a-hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-yl ester | 1269760-77-1

• 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
• 英文名称: ethyl carbamic acid 1,8-diacetyl-3a-hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-yl ester
• CAS: 1269760-77-1
• 化学式: C₁₇H₂₁N₃O₅
• 分子量: 347.371
• InChiKey: FAYLCKSZNCHBSS-NVXWUHKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.93
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  99.18
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  在 四丁基氟化铵 、 sodium methylate 、 sodium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.5h， 生成 ethyl carbamic acid 1,8-diacetyl-3a-hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-yl ester
  参考文献：
  名称：

  Selective inhibition of butyrylcholinesterase by singlet oxygen-generated melatonin derivatives

  摘要：

  The inhibition of cholinesterases plays a crucial role in a therapy of neurodegenerative diseases, including Alzheimer's disease. Especially, butyrylcholinesterase (BChE) has recently gained special interest. On the other hand, compounds having antioxidative properties may have a beneficial role in slowing down neurodegeneration processes. To combine these two effects, we synthesized a series of new derivatives of melatonin, which is a strong antioxidant, possessing structural elements essential for the inhibitory activity against cholinesterase. The structure of the new compounds was confirmed by NMR spectroscopy and mass spectrometry, and their activity against cholinesterases was measured in vitro using modified Ellman's method. The compounds obtained showed a high inhibitory activity, together with a strong selectivity against BChE. These results may point at new area of interest in a research on cholinesterase inhibitors.

  DOI：

  10.1111/j.1600-079x.2010.00766.x