2-[4-(3-diphenylaminopropyl)piperazin-1-yl]ethylamine | 916140-65-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-[4-(3-diphenylaminopropyl)piperazin-1-yl]ethylamine
• 英文别名: N-[3-[4-(2-aminoethyl)piperazin-1-yl]propyl]-N-phenylaniline
• CAS: 916140-65-3
• 化学式: C₂₁H₃₀N₄
• 分子量: 338.496
• InChiKey: QUCAAGNNMYANJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  35.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[4-(3-diphenylaminopropyl)piperazin-1-yl]ethylamine 、 6,9-dichloro-2-methoxyacridine 以 苯酚 为溶剂， 反应 18.0h， 以58%的产率得到N-(6-chloro-2-methoxyacridin-9-yl)-N-{2-[4-(3-diphenylaminopropyl)piperazin-1-yl]ethyl}amine
  参考文献：
  名称：

  A Chimeric Ligand Approach Leading to Potent Antiprion Active Acridine Derivatives:  Design, Synthesis, and Biological Investigations

  摘要：

  Human transmissible neurodegenerations including Creutzfeldt-Jakob disease are unique, since they are caused by prions, an infectious agent that replicates without nucleic acids but instead by inducing conversion of a host-resident normal prion protein to a misfolded conformational isoform. For pharmacotherapy of these unusual diseases, tricyclic heterocyclic compounds such as quinacrine have been considered, but with ambiguous success in vivo, so far. On the basis of the synergistic antiprion effects of quinacrine and iminodibenzyl derivatives, we introduce a novel class of potential pharmaceuticals representing structural chimeras of quinacrine and imipramine analogues. We describe the chemical synthesis and bioassays of a focused library of these compounds. The most potent target compound 2a revealed an EC50 value of 20 nM determined with a cell model of prion disease, thus substantially improving the antiprion efficacy of quinacrine.

  DOI：

  10.1021/jm060773j
• 作为产物：
  描述：

  1-哌嗪基乙腈 在 lithium aluminium tetrahydride 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 2-[4-(3-diphenylaminopropyl)piperazin-1-yl]ethylamine
  参考文献：
  名称：

  A Chimeric Ligand Approach Leading to Potent Antiprion Active Acridine Derivatives:  Design, Synthesis, and Biological Investigations

  摘要：

  Human transmissible neurodegenerations including Creutzfeldt-Jakob disease are unique, since they are caused by prions, an infectious agent that replicates without nucleic acids but instead by inducing conversion of a host-resident normal prion protein to a misfolded conformational isoform. For pharmacotherapy of these unusual diseases, tricyclic heterocyclic compounds such as quinacrine have been considered, but with ambiguous success in vivo, so far. On the basis of the synergistic antiprion effects of quinacrine and iminodibenzyl derivatives, we introduce a novel class of potential pharmaceuticals representing structural chimeras of quinacrine and imipramine analogues. We describe the chemical synthesis and bioassays of a focused library of these compounds. The most potent target compound 2a revealed an EC50 value of 20 nM determined with a cell model of prion disease, thus substantially improving the antiprion efficacy of quinacrine.

  DOI：

  10.1021/jm060773j

文献信息

• A Chimeric Ligand Approach Leading to Potent Antiprion Active Acridine Derivatives:  Design, Synthesis, and Biological Investigations
  作者：Silke Dollinger、Stefan Löber、Ralf Klingenstein、Carsten Korth、Peter Gmeiner

  DOI：10.1021/jm060773j

  日期：2006.11.1

  Human transmissible neurodegenerations including Creutzfeldt-Jakob disease are unique, since they are caused by prions, an infectious agent that replicates without nucleic acids but instead by inducing conversion of a host-resident normal prion protein to a misfolded conformational isoform. For pharmacotherapy of these unusual diseases, tricyclic heterocyclic compounds such as quinacrine have been considered, but with ambiguous success in vivo, so far. On the basis of the synergistic antiprion effects of quinacrine and iminodibenzyl derivatives, we introduce a novel class of potential pharmaceuticals representing structural chimeras of quinacrine and imipramine analogues. We describe the chemical synthesis and bioassays of a focused library of these compounds. The most potent target compound 2a revealed an EC50 value of 20 nM determined with a cell model of prion disease, thus substantially improving the antiprion efficacy of quinacrine.