3-bromo-9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole | 1227413-55-9

• 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: 3-bromo-9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole
• 英文别名: 3-bromo-9-[2-(2-methoxyethoxy)ethyl]carbazole
• CAS: 1227413-55-9
• 化学式: C₁₇H₁₈BrNO₂
• 分子量: 348.239
• InChiKey: FFTHBXAPWWLHMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  23.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole 在 正丁基锂 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole-3-carbaldehyde
  参考文献：
  名称：

  Imaging Beta-Amyloid Peptides and Inhibition of Beta-Amyloid Peptide Aggregation

  摘要：

  本发明涉及一种检测和监测与神经退行性疾病相关的β-淀粉样肽聚集的方法，以及利用基于咔唑的荧光物质治疗和/或预防神经退行性疾病。具体来说，本发明提供了一种在体外和/或体内标记和成像β-淀粉样（Aβ）肽、寡聚体和纤维的方法，以及利用本发明的基于咔唑的荧光物质治疗和/或预防阿尔茨海默病的方法。

  公开号：

  US20120269738A1
• 作为产物：
  描述：

  二乙二醇单甲醚 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 氯仿 、 水 为溶剂， 生成 3-bromo-9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole
  参考文献：
  名称：

  Cyanine fluorophores for cellular protection against ROS in stimulated macrophages and two-photon ROS detection

  摘要：

  报道了一种新型的生物相容性和巨噬细胞膜渗透性的基于咔唑的青蛋白探针，用于ROS检测和细胞保护。

  DOI：

  10.1039/c5ob00643k

文献信息

• Imaging Beta-Amyloid Peptides Aggregation
  申请人：Hong Kong Baptist University

  公开号：US20160243264A1

  公开（公告）日：2016-08-25

  The present invention is in the field of pharmaceuticals and chemical industries. In particular, one aspect of the present invention relates to methods for labeling, imaging and detecting the beta-amyloid (Aβ) peptides, oligomers, and fibrils in vitro and in vivo via magnetic resonance and florescence imaging by using modified carbazole-based fluorophores. A further aspect of the present invention relates to a method of reducing and preventing aggregation of beta-amyloid peptides for Alzheimer's disease (AD) as well as of treating and/or preventing Alzheimer's disease by using the modified carbazole-based fluorophore. The modified carbazole-based fluorophore according to an embodiment of the present invention is prepared by conjugating a carbazole-based fluorophore with magnetic nanoparticles to form a conjugate which is permeable to blood brain barrier of a subject being introduced therewith.

  本发明涉及制药和化工行业。具体而言，本发明的一个方面涉及使用改良的基于咔唑的荧光物质通过磁共振和荧光成像在体内和体外标记、成像和检测β-淀粉样蛋白（Aβ）肽、寡聚体和纤维的方法。本发明的另一个方面涉及一种减少和预防β-淀粉样蛋白在阿尔茨海默病（AD）中聚集的方法，以及使用改良的基于咔唑的荧光物质治疗和/或预防阿尔茨海默病的方法。根据本发明实施例的改良基于咔唑的荧光物质是通过将基于咔唑的荧光物质与磁性纳米颗粒偶联而制备的，形成的共轭物质能够穿透引入的受试者的血脑屏障。
• Inhibition of Beta-Amyloid Peptide Aggregation by Multifunctional Carbazole-Based Fluorophores
  作者：Wanggui Yang、Yi Wong、Olivia T. W. Ng、Li-Ping Bai、Daniel W. J. Kwong、Ya Ke、Zhi-Hong Jiang、Hung-Wing Li、Ken K. L. Yung、Man Shing Wong

  DOI：10.1002/anie.201104150

  日期：2012.2.20

  Stopping aggregation: Carbazole‐based cyanine fluorophores bind selectively to the Aβ(1–40) peptide and its aggregates which are responsible for causing Alzheimer's disease. One of these fluorophores, SLOH, exerts a strong inhibitory effect on Aβ(1–40) fibrillogenesis (see scheme) and can pass through the blood‐brain barrier making it a potential therapeutic agent for Alzheimer's disease.

  停止聚集：基于咔唑的花青荧光团与Aβ （1–40）肽及其聚集体选择性结合，而Aβ （1–40）肽及其聚集体可引起阿尔茨海默氏病。其中的一种荧光团SLOH对Aβ （1–40）的原纤维形成具有很强的抑制作用（参见方案），并且可以穿过血脑屏障，使其成为阿尔茨海默氏病的潜在治疗剂。
• Imaging beta-amyloid peptides and inhibition of beta-amyloid peptide aggregation
  申请人：Yang Wanggui

  公开号：US09156814B2

  公开（公告）日：2015-10-13

  The present invention relates to methods of detecting and monitoring aggregation of beta-amyloid peptides which are associated with neurodegenerative diseases as well as treating and/or preventing the neurodegenerative diseases by using carbazole-based fluorophores. In particular, the present invention provides methods for labeling and imaging the beta-amyloid (Aβ) peptides, oligomers, and fibrils in vitro and/or in vivo, as well as treating and/or preventing Alzheimer's disease by using the carbazole-based fluorophores of the present invention.

  本发明涉及一种使用基于咔唑的荧光染料检测和监测与神经退行性疾病相关的β-淀粉样肽聚集的方法，以及使用基于咔唑的荧光染料治疗和/或预防神经退行性疾病。特别地，本发明提供了一种在体内和/或体外标记和成像β-淀粉样肽（Aβ）肽段、寡聚体和纤维的方法，以及使用本发明的基于咔唑的荧光染料治疗和/或预防阿尔茨海默病的方法。
• Cyanines as New Fluorescent Probes for DNA Detection and Two-Photon Excited Bioimaging
  作者：Xin Jiang Feng、Po Lam Wu、Frédéric Bolze、Heidi W. C. Leung、King Fai Li、Nai Ki Mak、Daniel W. J. Kwong、Jean-François Nicoud、Kok Wai Cheah、Man Shing Wong

  DOI：10.1021/ol100474b

  日期：2010.5.21

  A series of cyanine fluorophores based on fused aromatics as an electron donor for DNA sensing and two-photon bioimaging were synthesized, among which the carbazole-based biscyanine exhibits high sensitivity and efficiency as a fluorescent light-up probe for dsDNA, which shows selective binding toward the AT-rich regions. The synergetic effect of the bischromophoric skeleton gives a several-fold enhancement in a two-photon absorption cross-section as well as a 25- to 100-fold enhancement in two-photon excited fluorescence upon dsDNA binding.
• Fluorescence-Enhanced Chemosensor for Metal Cation Detection Based on Pyridine and Carbazole
  作者：Xin Jiang Feng、Pin Zhan Tian、Zheng Xu、Shao Fu Chen、Man Shing Wong

  DOI：10.1021/jo401808c

  日期：2013.11.15

  A series of donor-acceptor systems incorporating a carbazole moiety as the donating unit and pyridine moiety as the accepting unit have been designed and synthesized. The spectroscopic and electrochemical behaviors of the carbazole derivatives demonstrate that the carbazole unit interacts with the electron-accepting group through the pi-conjugated spacer, thus leading to the intramolecular charge transfer (ICT). The pyridine-substituted carbazole derivatives show significant sensing and coordinating properties toward a wide range of metal cations. Compound S2 exhibits fluorescence enhancement upon association with transition metal cations, and compound V3 shows high selectivity for Cu2+ among this series of materials. DFT calculations indicate the different association abilities of the dyes and the enhancement of ICT upon addition of the metal cations.