N1-(3-aminopropyl)-N3-(1,2,3,4-tetrahydroacridin-9-yl)propane-1,3-diamine

• 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: N1-(3-aminopropyl)-N3-(1,2,3,4-tetrahydroacridin-9-yl)propane-1,3-diamine
• 英文别名: N1-[3-(1,2,3,4-tetrahydroacridin-9-ylamino)propyl]propane-1,3-diamine；N'-[3-(1,2,3,4-tetrahydroacridin-9-ylamino)propyl]propane-1,3-diamine
• 化学式: C₁₉H₂₈N₄
• 分子量: 312.458
• InChiKey: WOPFRKWPOKZFGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  63
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N1-(3-aminopropyl)-N3-(1,2,3,4-tetrahydroacridin-9-yl)propane-1,3-diamine 、 3,8-Bis-acetylamino-5-(3-bromo-propyl)-6-phenyl-phenanthridinium; chloride 以 甲醇 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  Propidium-Based Polyamine Ligands as Potent Inhibitors of Acetylcholinesterase and Acetylcholinesterase-Induced Amyloid-β Aggregation

  摘要：

  Heterodimers 4 and 5 were effective inhibitors of acetylcholinesterase (AChE) activity and AChE-induced amyloid-beta (Abeta) aggregation. The peculiar biological profile of 4 can be relevant in studying the molecular basis underlying the nonclassical action of AChE and in addressing the question whether AChE inhibitors can affect the neurotoxic cascade leading to Alzheimer's disease. Compound 4 emerged as the most potent heterodimer so far available to inhibit AChE-induced Abeta aggregation.

  DOI：

  10.1021/jm049156q
• 作为产物：
  描述：

  3,3'-二氨基二丙基胺 、 9-氯-1,2,3,4-四氢吖啶 在 potassium iodide 作用下， 以 戊醇 为溶剂， 反应 24.0h， 以42%的产率得到N1-(3-aminopropyl)-N3-(1,2,3,4-tetrahydroacridin-9-yl)propane-1,3-diamine
  参考文献：
  名称：

  Propidium-Based Polyamine Ligands as Potent Inhibitors of Acetylcholinesterase and Acetylcholinesterase-Induced Amyloid-β Aggregation

  摘要：

  Heterodimers 4 and 5 were effective inhibitors of acetylcholinesterase (AChE) activity and AChE-induced amyloid-beta (Abeta) aggregation. The peculiar biological profile of 4 can be relevant in studying the molecular basis underlying the nonclassical action of AChE and in addressing the question whether AChE inhibitors can affect the neurotoxic cascade leading to Alzheimer's disease. Compound 4 emerged as the most potent heterodimer so far available to inhibit AChE-induced Abeta aggregation.

  DOI：

  10.1021/jm049156q

文献信息

• Parallel Synthesis, Evaluation, and Preliminary Structure−Activity Relationship of 2,5-Diamino-1,4-benzoquinones as a Novel Class of Bivalent Anti-Prion Compound
  作者：Salvatore Bongarzone、Hoang Ngoc Ai Tran、Andrea Cavalli、Marinella Roberti、Paolo Carloni、Giuseppe Legname、Maria Laura Bolognesi

  DOI：10.1021/jm100882t

  日期：2010.11.25

  A library of 11 entries, featuring a 2,5-diamino-1,4-benzoquinones nucleus as spacer connecting two aromatic prion recognition motifs, was designed and evaluated against prion infection. Notably. 6-chloro-1,2,3,4-tetrithydroacridine 10 showed an EC50 of 0.17 mu M, which was lower than that displayed by reference compound BiCappa. More importantly, 10 possessed the capability to contrast prion fibril formation and oxidative stress, together with a low cytotoxicity. This study further corroborates the bivalent strategy as a viable approach to the rational design of anti-prion chemical probes.
• Propidium-Based Polyamine Ligands as Potent Inhibitors of Acetylcholinesterase and Acetylcholinesterase-Induced Amyloid-β Aggregation
  作者：Maria Laura Bolognesi、Vincenza Andrisano、Manuela Bartolini、Rita Banzi、Carlo Melchiorre

  DOI：10.1021/jm049156q

  日期：2005.1.1

  Heterodimers 4 and 5 were effective inhibitors of acetylcholinesterase (AChE) activity and AChE-induced amyloid-beta (Abeta) aggregation. The peculiar biological profile of 4 can be relevant in studying the molecular basis underlying the nonclassical action of AChE and in addressing the question whether AChE inhibitors can affect the neurotoxic cascade leading to Alzheimer's disease. Compound 4 emerged as the most potent heterodimer so far available to inhibit AChE-induced Abeta aggregation.