N1-[3-(1,2,3,4-tetrahydroacridin-9-ylamino)propyl]-3-[cyclohexyl(ethyl)amino]propanamide

• 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-(1,2,3,4-tetrahydroacridin-9-ylamino)propyl]-3-[cyclohexyl(ethyl)amino]propanamide
• 英文别名: 3-[cyclohexyl(ethyl)amino]-N-[3-(1,2,3,4-tetrahydroacridin-9-ylamino)propyl]propanamide
• 化学式: C₂₇H₄₀N₄O
• 分子量: 436.641
• InChiKey: GDXNXPQGVOTDDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  57.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  9-氯-1,2,3,4-四氢吖啶 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 、 苯酚 为溶剂， 反应 8.17h， 生成 N1-[3-(1,2,3,4-tetrahydroacridin-9-ylamino)propyl]-3-[cyclohexyl(ethyl)amino]propanamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Tacrine Derivatives and Tacrine–Coumarin Hybrids as Cholinesterase Inhibitors

  摘要：

  A series of novel tacrine derivatives and tacrine-coumarin heterodimers were designed, synthesized, and biologically evaluated for their potential inhibitory effect on both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). Of these compounds, tacrine-coumarin heterodimer 7c and tacrine derivative 6b were found to be the most potent inhibitors of human AChE (hAChE), demonstrating IC50 values of 0.0154 and 0.0263 μM. Ligands 6b, 6c, and 7c exhibited the highest levels of inhibitory activity against human BuChE (hBuChE), demonstrating IC50 values that range from 0.228 to 0.328 μM. Docking studies were performed in order to predict the binding modes of compounds 6b and 7c with hAChE/hBuChE.

  DOI：

  10.1021/jm5008648

文献信息

• Synthesis and Biological Evaluation of Novel Tacrine Derivatives and Tacrine–Coumarin Hybrids as Cholinesterase Inhibitors
  作者：Slavka Hamulakova、Ladislav Janovec、Martina Hrabinova、Katarina Spilovska、Jan Korabecny、Pavol Kristian、Kamil Kuca、Jan Imrich

  DOI：10.1021/jm5008648

  日期：2014.8.28

  A series of novel tacrine derivatives and tacrine-coumarin heterodimers were designed, synthesized, and biologically evaluated for their potential inhibitory effect on both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). Of these compounds, tacrine-coumarin heterodimer 7c and tacrine derivative 6b were found to be the most potent inhibitors of human AChE (hAChE), demonstrating IC50 values of 0.0154 and 0.0263 μM. Ligands 6b, 6c, and 7c exhibited the highest levels of inhibitory activity against human BuChE (hBuChE), demonstrating IC50 values that range from 0.228 to 0.328 μM. Docking studies were performed in order to predict the binding modes of compounds 6b and 7c with hAChE/hBuChE.