(3aS,8aR)-1-Benzyl-5-methoxy-3a-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indole-8-carbaldehyde | 290294-26-7

• 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: (3aS,8aR)-1-Benzyl-5-methoxy-3a-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indole-8-carbaldehyde
• 英文别名: (3aR,8bS)-3-benzyl-7-methoxy-8b-methyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-4-carbaldehyde
• CAS: 290294-26-7
• 化学式: C₂₀H₂₂N₂O₂
• 分子量: 322.407
• InChiKey: MTACZCUXZVIOFY-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aS,8aR)-1-Benzyl-5-methoxy-3a-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indole-8-carbaldehyde 在 palladium dihydroxide 氢气 、 sodium 、 三溴化硼 作用下， 以 乙醚 、 二氯甲烷 、 异丙醇 为溶剂， 反应 1.0h， 生成 (-)-N¹,N⁸-bisnorcymserine
  参考文献：
  名称：

  A practical conversion of natural physostigmine into the potent butyrylcholinesterase inhibitor N1,N8-bisnorcymserine

  摘要：

  A rapid novel synthetic route to the potent reversible butyrylcholinesterase inhibitor (-)-N-1,N-8-bis-norcymserine (1) is reported from physostigmine (2) in a 20% total yield. Details on the formation of the imino-quinone 6 obtained in the oxidation of N-1-benzylnoresermethole (4) and its conversion into N-1-bis-noreseroline (7) are given. As expected, the product of this synthesis, (1), had identical biological activity to the same agent produced by total synthesis. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00740-1
• 作为产物：
  描述：

  氧化毒扁豆碱 在 氢氧化钾 、 重铬酸吡啶 、 碳酸氢钠 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 (3aS,8aR)-1-Benzyl-5-methoxy-3a-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indole-8-carbaldehyde
  参考文献：
  名称：

  A practical conversion of natural physostigmine into the potent butyrylcholinesterase inhibitor N1,N8-bisnorcymserine

  摘要：

  A rapid novel synthetic route to the potent reversible butyrylcholinesterase inhibitor (-)-N-1,N-8-bis-norcymserine (1) is reported from physostigmine (2) in a 20% total yield. Details on the formation of the imino-quinone 6 obtained in the oxidation of N-1-benzylnoresermethole (4) and its conversion into N-1-bis-noreseroline (7) are given. As expected, the product of this synthesis, (1), had identical biological activity to the same agent produced by total synthesis. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00740-1

文献信息

• Compound useful in the treatment or prevention of cognitive disorders associated with diabetes and associated methods
  申请人：Greig H. Nigel

  公开号：US20060105940A1

  公开（公告）日：2006-05-18

  Described is the efficient synthesis of an easy to manipulate and utilize, soluble tartrate salt of a potent, reversible butyrylcholinesterase inhibitor, (−)-(3aS)-3a-methyl-1,2,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indol-5-yl N—4′-isopropylphenylcarbamate (“MHI tartrate”), for use in altering the enzymatic activity of butyrylcholinesterase and/or acetylcholinesterase in a subject exhibiting or predicted to exhibit cognitive disorders associated with diabetes. Subjects may be suffering from or predicted to suffer from abnormal acetylcholinesterase and/or butyrylcholinesterase activity levels or from an inability to metabolize or catabolize blood sugar normally. The method comprises administering to the subject an effective amount of MHI tartrate dispensable in discrete pharmaceutically useful dosages. MHI tartrate effectively inhibits both acetylcholinesterase and butyrylcholinesterases and additionally is highly selective for butyrylcholinesterase over acetylcholinesterase.

  描述了一种高效合成易于操纵和利用的可溶性酒石酸盐，用作对展现或预测将展现与糖尿病相关的认知障碍的受试者中的丁酰胆碱酯酶和/或乙酰胆碱酯酶的酶活性进行改变的药物，该药物是一种有效的、可逆的丁酰胆碱酯酶抑制剂，(−)-(3aS)-3a-甲基-1,2,3,3a,8,8a-六氢吡咯并-[2,3-b]吲哚-5-基-N-4'-异丙基苯甲酸酯（“MHI酒石酸盐”）。受试者可能正在受苦于或预测将受苦于异常的乙酰胆碱酯酶和/或丁酰胆碱酯酶活性水平，或者由于无法正常代谢或降解血糖。该方法包括向受试者投予MHI酒石酸盐的有效量，可分配为离散的药用剂量。MHI酒石酸盐有效地抑制了乙酰胆碱酯酶和丁酰胆碱酯酶，并且对丁酰胆碱酯酶的选择性高于对乙酰胆碱酯酶的选择性。