8-(1,2,3,4-tetrahydro-9-acridine-9-yl)-7-octenyl-1-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-(1,2,3,4-tetrahydro-9-acridine-9-yl)-7-octenyl-1-amine
• 英文别名: (Z)-8-(1,2,3,4-tetrahydroacridin-9-yl)oct-7-en-1-amine
• 化学式: C₂₁H₂₈N₂
• 分子量: 308.467
• InChiKey: ALFSNDDQECVHJK-WZUFQYTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-(1,2,3,4-tetrahydro-9-acridine-9-yl)-7-octenyl-1-amine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 戊醇 为溶剂， 20.0~160.0 ℃ 、275.79 kPa 条件下， 反应 16.0h， 生成 N-[8-(1,2,3,4-tetrahydroacridin-9-yl)octyl]-1,2,3,4-tetrahydroacridin-9-amine
  参考文献：
  名称：

  Development of Molecular Probes for the Identification of Extra Interaction Sites in the Mid-Gorge and Peripheral Sites of Butyrylcholinesterase (BuChE). Rational Design of Novel, Selective, and Highly Potent BuChE Inhibitors

  摘要：

  Tacrine heterobivalent ligands were designed as novel and reversible inhibitors of cholinesterases. On the basis of the investigation of the active site gorge topology of butyrylcholinesterase (BuChE) and acetylcholinesterase (AChE) and by using flexible docking procedures, molecular modeling studies formulated the hypothesis of extra interaction sites in the active gorge of hBuChE, namely, a mid-gorge interaction site and a peripheral interaction site. The design strategy led to novel BuChE inhibitors, balancing potency and selectivity. Among the compounds identified, the heterobivalent ligand 4m, containing an amide nitrogen and a sulfur atom at the 8-membered tether level, is one of the most potent and selective BuChE inhibitors described to date. The novel inhibitors, bearing postulated key features, validated the hypothesis of the presence of extra interaction sites within the hBuChE active site gorge.

  DOI：

  10.1021/jm049510k
• 作为产物：
  描述：

  1,2,3,4-四氢丫啶-9-羧酸 在 lithium aluminium tetrahydride 、 potassium tert-butylate 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 6.5h， 生成 8-(1,2,3,4-tetrahydro-9-acridine-9-yl)-7-octenyl-1-amine
  参考文献：
  名称：

  Development of Molecular Probes for the Identification of Extra Interaction Sites in the Mid-Gorge and Peripheral Sites of Butyrylcholinesterase (BuChE). Rational Design of Novel, Selective, and Highly Potent BuChE Inhibitors

  摘要：

  Tacrine heterobivalent ligands were designed as novel and reversible inhibitors of cholinesterases. On the basis of the investigation of the active site gorge topology of butyrylcholinesterase (BuChE) and acetylcholinesterase (AChE) and by using flexible docking procedures, molecular modeling studies formulated the hypothesis of extra interaction sites in the active gorge of hBuChE, namely, a mid-gorge interaction site and a peripheral interaction site. The design strategy led to novel BuChE inhibitors, balancing potency and selectivity. Among the compounds identified, the heterobivalent ligand 4m, containing an amide nitrogen and a sulfur atom at the 8-membered tether level, is one of the most potent and selective BuChE inhibitors described to date. The novel inhibitors, bearing postulated key features, validated the hypothesis of the presence of extra interaction sites within the hBuChE active site gorge.

  DOI：

  10.1021/jm049510k