2-phenyl-9-(p-tolyl)-9H-carbazole | 1469876-03-6

• 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: 2-phenyl-9-(p-tolyl)-9H-carbazole
• 英文别名: 9-(4-Methylphenyl)-2-phenylcarbazole；9-(4-methylphenyl)-2-phenylcarbazole
• CAS: 1469876-03-6
• 化学式: C₂₅H₁₉N
• 分子量: 333.433
• InChiKey: VUTMYRGGYVAPRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-iodo-1,1':4',1''-terphenyl 在 三氟甲磺酸 、 copper diacetate 、 sodium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙二醇 、 异丙醇 为溶剂， 反应 17.0h， 生成 2-phenyl-9-(p-tolyl)-9H-carbazole
  参考文献：
  名称：

  Discovery of novel N-substituted carbazoles as neuroprotective agents with potent anti-oxidative activity

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2013.07.029

文献信息

• Transition-Metal-Free Synthesis of Carbazoles and Indoles by an S_NAr-Based “Aromatic Metamorphosis” of Thiaarenes
  作者：M. Bhanuchandra、Kei Murakami、Dhananjayan Vasu、Hideki Yorimitsu、Atsuhiro Osuka

  DOI：10.1002/anie.201503671

  日期：2015.8.24

  dibenzothiophenes, undergo nucleophilic aromatic substitution with anilines intermolecularly and then intramolecularly to yield the corresponding carbazoles in a single operation. The “aromatic metamorphosis” of dibenzothiophenes into carbazoles does not require any heavy metals. This strategy is also applicable to the synthesis of indoles. Since electron‐deficient thiaarene dioxides exhibit interesting reactivity

  通过母体二苯并噻​​吩的氧化容易制备的二苯并噻吩二氧化物在一次操作中在分子内然后在分子内经历苯胺的亲核芳香取代，然后生成分子内相应的咔唑。二苯并噻吩向咔唑的“芳香变形”不需要任何重金属。该策略也适用于吲哚的合成。由于缺电子的硫杂芳烃二氧化物表现出有趣的反应性，而相应的富电子氮杂芳烃则未观察到，因此，二氧化硫杂ar特定反应与基于S N Ar的芳族变态反应的结合，使得无过渡金属的结构成为可能。难以制备咔唑。
• Design, synthesis and biological evaluation of <i>N</i>-arylsulfonyl carbazoles as novel anticancer agents
  作者：Xin You、Daqian Zhu、Wenhua Lu、Yichen Sun、Shuang Qiao、Bingling Luo、Yongliang Du、Rongbiao Pi、Yumin Hu、Peng Huang、Shijun Wen

  DOI：10.1039/c8ra02939c

  日期：——

  this work, a set of structurally diverse synthetic carbazoles was screened for their anticancer activities. According to structure–activity relationship studies, carbazoles with an N-substituted sulfonyl group exhibited better anticancer activity. Moreover, compound 8h was discovered to show the most potent anticancer effects on Capan-2 cells by inducing apoptosis and cell cycle arrest in G2/M phase

  在这项工作中，筛选了一组结构多样的合成咔唑的抗癌活性。根据构效关系研究，具有N-取代磺酰基的咔唑表现出更好的抗癌活性。此外，发现化合物8h通过诱导 G2/M 期细胞凋亡和细胞周期停滞对 Capan-2 细胞显示出最有效的抗癌作用。最后，体内研究表明，8h在 PANC-1 和 Capan-2 异种移植模型中阻止了肿瘤生长，没有明显的毒性。
• 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
• 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.