N-((7-methoxy-9H-carbazol-4-yl)methyl)propan-2-amine | 1416580-16-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-((7-methoxy-9H-carbazol-4-yl)methyl)propan-2-amine
• 英文别名: N-[(7-methoxy-9H-carbazol-4-yl)methyl]propan-2-amine
• CAS: 1416580-16-9
• 化学式: C₁₇H₂₀N₂O
• 分子量: 268.359
• InChiKey: RQGBNHOWYVIADD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-((7-methoxy-9H-carbazol-4-yl)methyl)propan-2-amine 在 氢溴酸 作用下， 以 水 为溶剂， 反应 3.0h， 以71%的产率得到5-[(isopropylamino)methyl]-9H-carbazol-2-ol
  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：

  4-溴-3-硝基苯甲醚 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 偶氮二异丁腈 、 3-chlorobenzaldehyde N-[-(3-chlorophenyl)methylidene]hydrazone 、 sodium hydride 、 sodium carbonate 、 potassium carbonate 、 三苯基膦 、 potassium iodide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 、 mineral oil 为溶剂， 反应 26.0h， 生成 N-((7-methoxy-9H-carbazol-4-yl)methyl)propan-2-amine
  参考文献：
  名称：

  Ferulic acid–carbazole hybrid compounds: Combination of cholinesterase inhibition, antioxidant and neuroprotection as multifunctional anti-Alzheimer agents

  摘要：

  In order to search for novel multifunctional anti-Alzheimer agents, a series of ferulic acid-carbazole hybrid compounds were designed and synthesized. Ellman's assay revealed that the hybrid compounds showed moderate to potent inhibitory activity against the cholinesterases. Particularly, the AChE inhibition potency of compound 5k (IC50 1.9 mu M) was even 5-fold higher than that of galantamine. In addition, the target compounds showed pronounced antioxidant ability and neuroprotective property, especially against the ROS-induced toxicity. Notably, the neuroprotective effect of 5k was obviously superior to that of the mixture of ferulic acid and carbazole, indicating the therapeutic effect of the hybrid compound is better than the combination administration of the corresponding mixture. (c) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.01.010

文献信息

• Design, synthesis and biological evaluation of D-ring opened galantamine analogs as multifunctional anti-Alzheimer agents
  作者：Lei Fang、Xubin Fang、Shaohua Gou、Amelie Lupp、Isabell Lenhardt、Yanyan Sun、Zhangjian Huang、Yao Chen、Yihua Zhang、Christian Fleck

  DOI：10.1016/j.ejmech.2014.02.035

  日期：2014.4

  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.
• Ferulic acid–carbazole hybrid compounds: Combination of cholinesterase inhibition, antioxidant and neuroprotection as multifunctional anti-Alzheimer agents
  作者：Lei Fang、Mohao Chen、Zhikun Liu、Xubin Fang、Shaohua Gou、Li Chen

  DOI：10.1016/j.bmc.2016.01.010

  日期：2016.2

  In order to search for novel multifunctional anti-Alzheimer agents, a series of ferulic acid-carbazole hybrid compounds were designed and synthesized. Ellman's assay revealed that the hybrid compounds showed moderate to potent inhibitory activity against the cholinesterases. Particularly, the AChE inhibition potency of compound 5k (IC50 1.9 mu M) was even 5-fold higher than that of galantamine. In addition, the target compounds showed pronounced antioxidant ability and neuroprotective property, especially against the ROS-induced toxicity. Notably, the neuroprotective effect of 5k was obviously superior to that of the mixture of ferulic acid and carbazole, indicating the therapeutic effect of the hybrid compound is better than the combination administration of the corresponding mixture. (c) 2016 Elsevier Ltd. All rights reserved.