9-((4-ethylphenyl)sulfonyl)-9H-carbazole | 1469876-05-8

• 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-((4-ethylphenyl)sulfonyl)-9H-carbazole
• 英文别名: 9-tosyl-9H-carbazole；9-(4-Ethylphenyl)sulfonylcarbazole；9-(4-ethylphenyl)sulfonylcarbazole
• CAS: 1469876-05-8
• 化学式: C₂₀H₁₇NO₂S
• 分子量: 335.426
• InChiKey: PJRHTKPTSPPGCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-硝基联苯 在 盐酸 、 copper diacetate 、 sodium carbonate 、 一水合肼 、 乙二醇 、 间氯过氧苯甲酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 19.33h， 生成 9-((4-ethylphenyl)sulfonyl)-9H-carbazole
  参考文献：
  名称：

  通过将一锅铜催化的胺插入环状二苯并碘鎓中来合成咔唑，作为生成类似药物的化学文库的策略

  摘要：

  AbstractCarbazoles have attracted high interest among synthetic chemists due to their unique structural features and potential pharmacological activities. Compared to linear aryliodoniums, cyclic diphenyleneiodoniums are more inert and have not attracted much attention to their application as building blocks. Employing our synthetic strategy, diversified carbazoles can be efficiently obtained from a single cyclic diphenyleneiodonium under mild conditions. The reactions catalyzed by copper(II) acetate have provided a variety of carbazoles in modest to good yields with a broad range of amines including anilines, aliphatic amines and sulfonamides. Moreover, one of the obtained carbazoles has displayed an outstanding ability to protect HT‐22 neuronal cells from the damage induced by neurotoxins glutamate and homocysteic acid.magnified image

  DOI：

  10.1002/adsc.201300271

文献信息

• Discovery of novel N-substituted carbazoles as neuroprotective agents with potent anti-oxidative activity
  作者：Daqian Zhu、Meihui Chen、Min Li、Bingling Luo、Yang Zhao、Peng Huang、Fengtian Xue、Simona Rapposelli、Rongbiao Pi、Shijun Wen

  DOI：10.1016/j.ejmech.2013.07.029

  日期：2013.10

  Carbazole moiety is an important scaffold with a variety of biological applications, for example, anti-oxidative stress. Our previous synthesized carbazoles were screened for their neuroprotective properties against two individual oxidative stresses. Some of the new carbazole derivatives were observed with modest to good neuroprotective effects on neuronal cells HT22 against cell injury induced by glutamate or homocysteic acid (HCA). Substituents introduced to the carbazole ring system play crucial roles in their biological activities. In particular, a bulky group favors the neuroprotective activity of the compounds. One of the new compounds, 6, showed the best neuroprotective effects, which might result from its anti-oxidative activity with a GSH-independent mechanism. These findings might provide an alternative strategy for the development of novel carbazole derivatives for the treatment of CNS diseases such as Alzheimer's disease. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis of Carbazoles<i>via</i>One-Pot Copper-Catalyzed Amine Insertion into Cyclic Diphenyleneiodoniums as a Strategy to Generate a Drug-Like Chemical Library
  作者：Daqian Zhu、Qi Liu、Bingling Luo、Meihui Chen、Rongbiao Pi、Peng Huang、Shijun Wen

  DOI：10.1002/adsc.201300271

  日期：2013.8.12

  AbstractCarbazoles have attracted high interest among synthetic chemists due to their unique structural features and potential pharmacological activities. Compared to linear aryliodoniums, cyclic diphenyleneiodoniums are more inert and have not attracted much attention to their application as building blocks. Employing our synthetic strategy, diversified carbazoles can be efficiently obtained from a single cyclic diphenyleneiodonium under mild conditions. The reactions catalyzed by copper(II) acetate have provided a variety of carbazoles in modest to good yields with a broad range of amines including anilines, aliphatic amines and sulfonamides. Moreover, one of the obtained carbazoles has displayed an outstanding ability to protect HT‐22 neuronal cells from the damage induced by neurotoxins glutamate and homocysteic acid.magnified image