4-(6-bromohexyloxy)-9H-carbazole | 1047632-44-9

• 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: 4-(6-bromohexyloxy)-9H-carbazole
• 英文别名: 4-((6-bromohexyl)oxy)-9H-carbazole
• CAS: 1047632-44-9
• 化学式: C₁₈H₂₀BrNO
• 分子量: 346.267
• InChiKey: HVCPTGYTJYYKQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.66
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25.02
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-(6-bromohexyloxy)-9H-carbazole 、 berberrubine 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以49%的产率得到9-O-[2-(9H-carbazol-4-yloxy)hexyl]berberine bromide
  参考文献：
  名称：

  Synthesis, biological evaluation, and molecular modeling of berberine derivatives as potent acetylcholinesterase inhibitors

  摘要：

  By targeting the dual active sites of acetylcholinesterase (AChE), a new series of berberine derivatives was designed, synthesized, and evaluated as AChE inhibitors. Most of the derivatives inhibited AChE in the sub-micromolar range. Compound 8c, berberine linked with phenol by a 4-carbon spacer, showed the most potent inhibition of AChE. A kinetic study of AChE and BuChE indicated that a mix-competitive binding mode existed for these berberine derivatives. Molecular modeling studies confirmed that these hybrids target both the catalytic active site (CAS) and the peripheral anionic site (PAS) of AChE. This is the first report where AChE inhibitory activity has been associated with berberine as a lead molecule. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.035
• 作为产物：
  描述：

  1,6-二溴己烷 、 4-羟基咔唑 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以55%的产率得到4-(6-bromohexyloxy)-9H-carbazole
  参考文献：
  名称：

  Endowing TADF luminophors with AIE properties through adjusting flexible dendrons for highly efficient solution-processed nondoped OLEDs

  摘要：

  核-树状TADF发射体系的构建：将色团的行为从聚集引起猝灭转变为聚集诱导发射，以开发高性能完全溶液加工的无掺杂OLED。

  DOI：

  10.1039/d0sc02194f

文献信息

• Design, Synthesis, and Biological Evaluation of a New Series of Carvedilol Derivatives That Protect Sensory Hair Cells from Aminoglycoside-Induced Damage by Blocking the Mechanoelectrical Transducer Channel
  作者：Molly O’Reilly、Nerissa K. Kirkwood、Emma J. Kenyon、Rosemary Huckvale、Daire M. Cantillon、Simon J. Waddell、Simon E. Ward、Guy P. Richardson、Corné J. Kros、Marco Derudas

  DOI：10.1021/acs.jmedchem.8b01325

  日期：2019.6.13

  we found, may be mediated by a block of the hair cell's mechanoelectrical transducer (MET) channel, the major entry route for the AGs. To understand the full otoprotective potential of carvedilol, a series of 18 analogues were prepared and evaluated for their effect against AG-induced damage as well as their affinity for the MET channel. One derivative was found to confer greater protection than carvedilol

  氨基糖苷类 (AG) 是用于治疗严重细菌感染的广谱抗生素，但具有限制使用的副作用，包括不可逆的听力损失。在这里，我们评估了卡维地洛在小鼠耳蜗培养和体内斑马鱼试验中的耳保护特性，并研究了它的保护机制，我们发现这可能是由毛细胞的机电传感器 (MET) 通道（主要进入途径）的阻断介导的对于 AG。为了了解卡维地洛的全部耳部保护潜力，制备了一系列 18 种类似物，并评估了它们对 AG 引起的损伤的作用以及它们对 MET 通道的亲和力。发现一种衍生物在耳蜗培养中比卡维地洛本身具有更大的保护作用，并且与 MET 通道的结合更紧密。
• Exciplex Formation and Electromer Blocking for Highly Efficient Blue Thermally Activated Delayed Fluorescence OLEDs with All‐Solution‐Processed Organic Layers
  作者：Xinxin Ban、Feng Chen、Jie Pan、Yan Liu、Aiyun Zhu、Wei Jiang、Yueming Sun

  DOI：10.1002/chem.201904415

  日期：2020.3.9

  Highly efficient solution-processable emitters are greatly desired to develop low-cost organic light-emitting diodes (OLEDs). The recently developed thermally activated delayed fluorescence (TADF) materials are promising candidates, but blue TADF materials compatible with the all-solution-process have still not been achieved. Here, a series of TADF materials, named X-4CzCN, are developed by introducing

  迫切需要高效的可溶液处理的发射器，以开发低成本的有机发光二极管（OLED）。最近开发的热活化延迟荧光（TADF）材料是有前途的候选材料，但仍未实现与全溶液工艺兼容的蓝色TADF材料。在这里，通过将未结合的连接基引入大的单元，开发了一系列名为X-4CzCN的TADF材料，该连接基实现了高分子量从而增强了耐溶剂性，而又不影响蓝色TADF的特性。同时，外围包裹基团通过隔离能量转移和电荷转移通道而有效地抑制了三重态-三重态和三重态-极化子猝灭。光物理测量表明，外围单元的微小变化将对发光效率产生显着影响。外围单元体积的增加将使电致发光光谱发生蓝移，同时增强激基复合物的能量转移并阻止电聚合物的能量泄漏，可促进激子的利用。结果，经过完全溶液处理的蓝色OLED的CIE为（0.16，0.27），开启电压为2.9 eV，外部量子效率为20.6％。据我们所知，这是全溶液处理的具有蓝光发射的TADF OLED的第
• Exceeding 30 % External Quantum Efficiency in Non‐doped OLEDs Utilizing Solution Processable TADF Emitters with High Horizontal Dipole Orientation via Anchoring Strategy
  作者：Guimin Zhao、Dan Liu、Panpan Wang、Xinping Huang、Haowen Chen、Yuewei Zhang、Dongdong Zhang、Wei Jiang、Yueming Sun、Lian Duan

  DOI：10.1002/anie.202212861

  日期：2022.11.7

  An anchoring strategy was firstly proposed to generate solution processable TADF emitters from isotropic orientation to horizontal one by attaching bipolar 9,9′-spirobi[fluorene] subunits as anchoring groups onto TADF emitting core via flexible chains. With outstanding characteristics in pristine films, unprecedented EQEmaxs of 30.6 % and 25.6 % were achieved for solution processable non-doped OLEDs

  首先提出了一种锚定策略，通过将双极 9,9'-螺双 [芴] 亚基作为锚定基团通过柔性链连接到 TADF 发射核上，从而产生从各向同性方向到水平方向的可溶液处理的 TADF 发射器。凭借原始薄膜的出色特性，可溶液加工的非掺杂 OLED 和 TSF OLED 分别实现了前所未有的 30.6% 和 25.6% 的EQE最大值。
• Inhibition of Acetylcholinesterase, β-Amyloid Aggregation, and NMDA Receptors in Alzheimer’s Disease: A Promising Direction for the Multi-target-Directed Ligands Gold Rush
  作者：Michela Rosini、Elena Simoni、Manuela Bartolini、Andrea Cavalli、Luisa Ceccarini、Nicoleta Pascu、David W. McClymont、Andrea Tarozzi、Maria L. Bolognesi、Anna Minarini、Vincenzo Tumiatti、Vincenza Andrisano、Ian R. Mellor、Carlo Melchiorre

  DOI：10.1021/jm800577j

  日期：2008.8.1

  Alzheimer's disease (AD) is a multifactorial syndrome with several target proteins contributing to its etiology. To confront AD, an innovative strategy is to design single chemical entities able to simultaneously modulate more than one target. Here, we present compounds that inhibit acety1cholinesterase and NMDA receptor activity. Furthermore, these compounds inhibit AChE-induced AP aggregation and display antioxidant properties, emerging as lead candidates for treating AD.