N-benzyl-1-(7-methoxy-9-(phenylsulfonyl)-9H-carbazol-4-yl)methanamine | 1416580-45-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-1-(7-methoxy-9-(phenylsulfonyl)-9H-carbazol-4-yl)methanamine
• CAS: 1416580-45-4
• 化学式: C₂₇H₂₄N₂O₃S
• 分子量: 456.565
• InChiKey: DFNAGHFAQWGLNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  60.33
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-benzyl-1-(7-methoxy-9-(phenylsulfonyl)-9H-carbazol-4-yl)methanamine 在 吡啶 、 C.I.酸性橙108 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 N-benzyl-3-(4-hydroxy-3-methoxyphenyl)-N-((7-methoxy-9H-carbazol-4-yl)methyl)acrylamide
  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
• 作为产物：
  描述：

  2-methoxy-5-methyl-9-(phenylsulfonyl)-9H-carbazole 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 potassium carbonate 、 potassium iodide 作用下， 以 四氯化碳 、 丙酮 为溶剂， 反应 2.0h， 生成 N-benzyl-1-(7-methoxy-9-(phenylsulfonyl)-9H-carbazol-4-yl)methanamine
  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