(9-ethyl-9H-carbazol-3-yl)-carbamic acid phenyl ester

• 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: (9-ethyl-9H-carbazol-3-yl)-carbamic acid phenyl ester
• 英文别名: phenyl (9-ethyl-9H-carbazol-3-yl)carbamate；Phenyl N-(9-ethyl-9H-carbazol-3-YL)carbamate；phenyl N-(9-ethylcarbazol-3-yl)carbamate
• 化学式: C₂₁H₁₈N₂O₂
• mdl: MFCD03718047
• 分子量: 330.386
• InChiKey: DBNYVTNBODYYMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  43.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (9-ethyl-9H-carbazol-3-yl)-carbamic acid phenyl ester 在 一水合肼 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 10.0h， 生成 N-(9-ethyl-9H-carbazol-3-yl)-2-(4-(trifluoromethoxy)benzoyl)hydrazinecarboxamide
  参考文献：
  名称：

  Development of novel carbazole derivatives with effective multifunctional action against Alzheimer’s diseases: Design, synthesis, in silico, in vitro and in vivo investigation

  摘要：

  Carbazole based novel multifunctional agents has been rationally designed and synthesized as potential anti-Alzheimer agents. Multi-functional activity of these derivatives have been assessed by performing various in-vitro assays and these compounds appeared to be potent AChE inhibitors, A beta aggregation inhibitors, antioxidant and neuroprotective agents. Among the entire series, MT-1 and MT-6 were most potent multifunctional agents which displayed effective and selective AChE inhibition, A disaggregation, anti-oxidant and metal chelation action. Neuroprotective activity of MT-6 has been examined against H2O2 induced toxicity in SHSY-5Y cells and they have shown effective neuroprotection. Additionally, MT-6 did not display any significant toxicity in SHSY-5Y cells, indicating its non-toxic nature. Molecular docking and MD simulation studies have been also performed to explore molecular level interaction with AChE and A beta. Finally, MT-6 was evaluated against scopolamine induced dementia model of mice and this compound actively improved memory deficit and cognition impairment in scopolamine treated mice. Thus, novel carbazole derivative MT-6 has been explored as an effective and safe multifunctional agent against AD and this molecule may be used as a suitable lead for development of effective anti-Alzheimer agents in future.

  DOI：

  10.1016/j.bioorg.2019.103524
• 作为产物：
  描述：

  3-氨基-9-乙基咔唑 、 氯甲酸苯酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以88%的产率得到(9-ethyl-9H-carbazol-3-yl)-carbamic acid phenyl ester
  参考文献：
  名称：

  Development of novel carbazole derivatives with effective multifunctional action against Alzheimer’s diseases: Design, synthesis, in silico, in vitro and in vivo investigation

  摘要：

  Carbazole based novel multifunctional agents has been rationally designed and synthesized as potential anti-Alzheimer agents. Multi-functional activity of these derivatives have been assessed by performing various in-vitro assays and these compounds appeared to be potent AChE inhibitors, A beta aggregation inhibitors, antioxidant and neuroprotective agents. Among the entire series, MT-1 and MT-6 were most potent multifunctional agents which displayed effective and selective AChE inhibition, A disaggregation, anti-oxidant and metal chelation action. Neuroprotective activity of MT-6 has been examined against H2O2 induced toxicity in SHSY-5Y cells and they have shown effective neuroprotection. Additionally, MT-6 did not display any significant toxicity in SHSY-5Y cells, indicating its non-toxic nature. Molecular docking and MD simulation studies have been also performed to explore molecular level interaction with AChE and A beta. Finally, MT-6 was evaluated against scopolamine induced dementia model of mice and this compound actively improved memory deficit and cognition impairment in scopolamine treated mice. Thus, novel carbazole derivative MT-6 has been explored as an effective and safe multifunctional agent against AD and this molecule may be used as a suitable lead for development of effective anti-Alzheimer agents in future.

  DOI：

  10.1016/j.bioorg.2019.103524

文献信息

• Development of novel carbazole derivatives with effective multifunctional action against Alzheimer’s diseases: Design, synthesis, in silico, in vitro and in vivo investigation
  作者：Chandra Bhushan Mishra、Siddharth Gusain、Shruti Shalini、Shikha Kumari、Amresh Prakash、Namrata Kumari、Anita Kumari Yadav、Jyoti Kumari、Kundan Kumar、Manisha Tiwari

  DOI：10.1016/j.bioorg.2019.103524

  日期：2020.1

  Carbazole based novel multifunctional agents has been rationally designed and synthesized as potential anti-Alzheimer agents. Multi-functional activity of these derivatives have been assessed by performing various in-vitro assays and these compounds appeared to be potent AChE inhibitors, A beta aggregation inhibitors, antioxidant and neuroprotective agents. Among the entire series, MT-1 and MT-6 were most potent multifunctional agents which displayed effective and selective AChE inhibition, A disaggregation, anti-oxidant and metal chelation action. Neuroprotective activity of MT-6 has been examined against H2O2 induced toxicity in SHSY-5Y cells and they have shown effective neuroprotection. Additionally, MT-6 did not display any significant toxicity in SHSY-5Y cells, indicating its non-toxic nature. Molecular docking and MD simulation studies have been also performed to explore molecular level interaction with AChE and A beta. Finally, MT-6 was evaluated against scopolamine induced dementia model of mice and this compound actively improved memory deficit and cognition impairment in scopolamine treated mice. Thus, novel carbazole derivative MT-6 has been explored as an effective and safe multifunctional agent against AD and this molecule may be used as a suitable lead for development of effective anti-Alzheimer agents in future.