3-chloro-N-isopropyl-N-[(7-methoxy-9H-carbazol-4-yl)methyl]propanamide | 1416580-54-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-chloro-N-isopropyl-N-[(7-methoxy-9H-carbazol-4-yl)methyl]propanamide
• 英文别名: 3-chloro-N-[(7-methoxy-9H-carbazol-4-yl)methyl]-N-propan-2-ylpropanamide
• CAS: 1416580-54-5
• 化学式: C₂₀H₂₃ClN₂O₂
• 分子量: 358.868
• InChiKey: CLOCFLNFKMCUNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  45.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-chloro-N-isopropyl-N-[(7-methoxy-9H-carbazol-4-yl)methyl]propanamide 在 silver nitrate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以43%的产率得到N-isopropyl-N-[(7-methoxy-9H-carbazol-4-yl)methyl]-3-nitropropanamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of D-ring opened galantamine analogs as multifunctional anti-Alzheimer agents

  摘要：

  Facing the multifactorial nature of Alzheimer's disease, twelve dibenzofuran/carbazole derivatives, which can be considered as the D-ring opened analogs of galantamine, have been designed and synthesized as multifunctional anti-Alzheimer agents. In vitro tests revealed that compounds 3 and 5, which bear a nitrate moiety in the molecule, showed a potent inhibition activity towards AChE and compound 3 showed a good A beta 42 aggregation inhibitory activity. Moreover, 3 and 5 could also release a relative low concentration of NO in vitro and they did not show toxicity to neuronal cells, while exerted a neuroprotective effect against the A beta-induced toxicity. More importantly, compound 3 showed a significant spatial memory improving effect in vivo, and a good safety in the ex vivo toxicity study. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.035
• 作为产物：
  描述：

  N-((7-methoxy-9-(phenylsulfonyl)-9H-carbazol-4-yl)methyl)propan-2-amine 在 吡啶 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 3-chloro-N-isopropyl-N-[(7-methoxy-9H-carbazol-4-yl)methyl]propanamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of D-ring opened galantamine analogs as multifunctional anti-Alzheimer agents

  摘要：

  Facing the multifactorial nature of Alzheimer's disease, twelve dibenzofuran/carbazole derivatives, which can be considered as the D-ring opened analogs of galantamine, have been designed and synthesized as multifunctional anti-Alzheimer agents. In vitro tests revealed that compounds 3 and 5, which bear a nitrate moiety in the molecule, showed a potent inhibition activity towards AChE and compound 3 showed a good A beta 42 aggregation inhibitory activity. Moreover, 3 and 5 could also release a relative low concentration of NO in vitro and they did not show toxicity to neuronal cells, while exerted a neuroprotective effect against the A beta-induced toxicity. More importantly, compound 3 showed a significant spatial memory improving effect in vivo, and a good safety in the ex vivo toxicity study. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.035