N-benzyl-1,2,3,4,6,11a-hexahydrobenzo[b]quinolizin-11-imine | 256451-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-benzyl-1,2,3,4,6,11a-hexahydrobenzo[b]quinolizin-11-imine
• CAS: 256451-29-3
• 化学式: C₂₀H₂₂N₂
• 分子量: 290.408
• InChiKey: SPWRNOKSZKDQRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  15.6
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-benzyl-1,2,3,4,6,11a-hexahydrobenzo[b]quinolizin-11-imine 在 palladium on activated charcoal 盐酸 、 氢气 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 20.0 ℃ 、317.16 kPa 条件下， 反应 45.0h， 生成 N-[(11R,11aR)-2,3,4,6,11,11a-hexahydro-1H-benzo[b]quinolizin-11-yl]-2-(2-oxopyrrolidin-1-yl)acetamide
  参考文献：
  名称：

  Syntheses of benzoquinolizidine and benzoindolizidine derivatives as anti-amnesic agents

  摘要：

  Tacrine, one of the drugs available for Alzheimer's disease based on the cholinergic approach, suffers from considerable toxicity. Many analogues of tacrine have been prepared which retain the pharmacologically rich aminopyridine or aminoquinoline motifs. The current research was undertaken to produce an acetylcholinesterase inhibitor by employing 11-aminobenzoquinolizidines (4) and 10-aminobenzoindolizidines (5) as templates. Thus, we aimed to achieve three goals relative to tacrine: eliminate the pyridine and quinoline moieties and render the molecule less flat. Overall, the compounds we prepared were poorer inhibitors of acetylcholinesterase compared to tacrine. The single exception was compound 6f which exhibited an effect comparable to that of tacrine, but only at a dose of the order of 10(-3) M. However, despite the poor acetylcholinesterase inhibition by 6b, this compound proved to be an effective anti-amnesic agent at 45 mg/kg dose. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00078-4
• 作为产物：
  描述：

  1-苄基哌啶-2-羧酸 在 PPA 、 四氯化钛 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 20.0h， 生成 N-benzyl-1,2,3,4,6,11a-hexahydrobenzo[b]quinolizin-11-imine
  参考文献：
  名称：

  Syntheses of benzoquinolizidine and benzoindolizidine derivatives as anti-amnesic agents

  摘要：

  Tacrine, one of the drugs available for Alzheimer's disease based on the cholinergic approach, suffers from considerable toxicity. Many analogues of tacrine have been prepared which retain the pharmacologically rich aminopyridine or aminoquinoline motifs. The current research was undertaken to produce an acetylcholinesterase inhibitor by employing 11-aminobenzoquinolizidines (4) and 10-aminobenzoindolizidines (5) as templates. Thus, we aimed to achieve three goals relative to tacrine: eliminate the pyridine and quinoline moieties and render the molecule less flat. Overall, the compounds we prepared were poorer inhibitors of acetylcholinesterase compared to tacrine. The single exception was compound 6f which exhibited an effect comparable to that of tacrine, but only at a dose of the order of 10(-3) M. However, despite the poor acetylcholinesterase inhibition by 6b, this compound proved to be an effective anti-amnesic agent at 45 mg/kg dose. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00078-4