6-bromo-1,4-dimethyl-9-H-carbazole-3-carbaldehyde | 18073-21-7

• 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: 6-bromo-1,4-dimethyl-9-H-carbazole-3-carbaldehyde
• 英文别名: 6-Brom-3-formyl-1,4-dimethyl-carbazol；6-bromo-1,4-dimethyl-carbazole-3-carbaldehyde；6-Bromo-1,4-dimethyl-9H-carbazole-3-carbaldehyde；6-bromo-1,4-dimethyl-9H-carbazole-3-carbaldehyde
• CAS: 18073-21-7
• 化学式: C₁₅H₁₂BrNO
• 分子量: 302.17
• InChiKey: LJFSNATUOFWLPQ-UHFFFAOYSA-N

物化性质

• 熔点：
  267-268 °C
• 沸点：
  492.2±40.0 °C(Predicted)
• 密度：
  1.538±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-bromo-1,4-dimethyl-9-H-carbazole-3-carbaldehyde 在 sodium carbonate 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 生成 9-溴椭圆玫瑰树碱
  参考文献：
  名称：

  Ellipticines and 9-acridinylamines as inhibitors of d-alanine:d-alanine ligase

  摘要：

  D-Alanine:D-alanine ligase (Ddl), an intracellular bacterial enzyme essential for cell wall biosynthesis, is an attractive target for development of novel antimicrobial drugs. This study focused on an extensive evaluation of two families of Ddl inhibitors encountered in our previous research. New members of both families were obtained through similarity search and synthesis. Ellipticines and 9-acridinylamines were both found to possess inhibitory activity against Ddl from Escherichia coli and antimicrobial activity against E. coli and Staphylococcus aureus. Ellipticines with a quaternary methylpyridinium moiety were the most potent among all studied compounds, with MIC values as low as 2 mg/L in strains with intact efflux mechanisms. Antimicrobial activity of the studied compounds was connected to membrane damage, making their development as antibacterial drug candidates unlikely unless analogues devoid of this nonspecific effect can be discovered. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.020
• 作为产物：
  描述：

  5-溴吲哚 在 对甲苯磺酸 、 三氯氧磷 作用下， 以 乙醇 、 邻二氯苯 为溶剂， 反应 4.67h， 生成 6-bromo-1,4-dimethyl-9-H-carbazole-3-carbaldehyde
  参考文献：
  名称：

  设计，合成，DNA结合研究以及新型取代的双咔唑衍生物对人神经胶质瘤U87 MG细胞系的抗癌能力。

  摘要：

  在这篇研究论文中，我们报告了新型取代的双咔唑衍生物的设计和合成，这些衍生物以1 H和13 C NMR，高分辨率质谱（HRMS）为特征。根据不同的取代基及其在双咔唑支架中的位置，报道了这些化合物的SAR研究。通过MTT测定24小时，评估化合物对人神经胶质瘤U87 MG细胞系的体外细胞毒性。所述IC 50是化合物（值30-35，48-53和54-62）在从1.00μM-500μM的浓度范围进行了计算。化合物34显示出最显着的体外细胞毒性（IC 50对人类神经胶质瘤U87 MG细胞株的抗药性为3.9 µM），被发现优于用于治疗脑肿瘤的标准药物，如替莫唑胺（IC 50 = 100 µM）和卡莫司汀（IC 50 = 18.2 µM）。为了确定化合物34与CT-DNA的结合方式，使用了各种生物物理技术，例如紫外分光光度计，荧光，圆二色性，粘度，拓扑异构酶测定和分子对接分析。我们的结果表明化合物34与C

  DOI：

  10.1016/j.bioorg.2020.103911

文献信息

• Efficient microwave-assisted synthesis of ellipticine through<i>N</i>-(1,4-dimethyl-9<i>H</i>-carbazol-3-ylmethyl)-<i>N</i>- tosylaminoacetaldehyde diethyl acetal
  作者：Hsueh-Yun Lee、Grace Shiahuy Chen、Chien-Shu Chen、Ji-Wang Chern

  DOI：10.1002/jhet.319

  日期：——

  cyclization of ellipticine (1a) was dramatically improved through N‐(1,4‐dimethylcarbazol‐3‐ylmethyl)‐N‐tosylaminoacetaldehyde diethyl acetal with microwave irradiation. The overall yield of 1a starting from indole was significantly increased by 25‐fold. This new approach is superior to reported methods in yields and, reaction time, and it provides efficient access to a broad spectrum of ellipticine derivatives

  玫瑰树碱（1a）的D环环化中长期存在的问题，即低产率通过N-（1,4-二甲基咔唑-3-基甲基）N-甲苯磺酰基氨基乙醛二乙缩醛的微波辐射得到了显着改善。从吲哚开始的1a的总产量显着提高了25倍。这种新方法在收率和反应时间方面均优于已报道的方法，并且可以有效地获得广泛的玫瑰树碱衍生物。J.杂环化​​学。（2010）。
• Design, synthesis, DNA binding studies and evaluation of anticancer potential of novel substituted biscarbazole derivatives against human glioma U87 MG cell line
  作者：Nitin Kumar、Neetika Lal、Vishal Nemaysh、Pratibha Mehta Luthra

  DOI：10.1016/j.bioorg.2020.103911

  日期：2020.7

  In this research paper, we report the design and synthesis of novel substituted biscarbazole derivatives which were characterized by 1H and 13C NMR, high resolution mass spectroscopy (HRMS). The SAR study of the compounds is reported based on different substituents and their positions in the biscarbazole scaffold. In vitro cytotoxicity of the compounds was evaluated against human glioma U87 MG cell

  在这篇研究论文中，我们报告了新型取代的双咔唑衍生物的设计和合成，这些衍生物以1 H和13 C NMR，高分辨率质谱（HRMS）为特征。根据不同的取代基及其在双咔唑支架中的位置，报道了这些化合物的SAR研究。通过MTT测定24小时，评估化合物对人神经胶质瘤U87 MG细胞系的体外细胞毒性。所述IC 50是化合物（值30-35，48-53和54-62）在从1.00μM-500μM的浓度范围进行了计算。化合物34显示出最显着的体外细胞毒性（IC 50对人类神经胶质瘤U87 MG细胞株的抗药性为3.9 µM），被发现优于用于治疗脑肿瘤的标准药物，如替莫唑胺（IC 50 = 100 µM）和卡莫司汀（IC 50 = 18.2 µM）。为了确定化合物34与CT-DNA的结合方式，使用了各种生物物理技术，例如紫外分光光度计，荧光，圆二色性，粘度，拓扑异构酶测定和分子对接分析。我们的结果表明化合物34与C
• Ellipticines and 9-acridinylamines as inhibitors of d-alanine:d-alanine ligase
  作者：Blaž Vehar、Martina Hrast、Andreja Kovač、Janez Konc、Katherine Mariner、Ian Chopra、Alex O’Neill、Dušanka Janežič、Stanislav Gobec

  DOI：10.1016/j.bmc.2011.07.020

  日期：2011.9

  D-Alanine:D-alanine ligase (Ddl), an intracellular bacterial enzyme essential for cell wall biosynthesis, is an attractive target for development of novel antimicrobial drugs. This study focused on an extensive evaluation of two families of Ddl inhibitors encountered in our previous research. New members of both families were obtained through similarity search and synthesis. Ellipticines and 9-acridinylamines were both found to possess inhibitory activity against Ddl from Escherichia coli and antimicrobial activity against E. coli and Staphylococcus aureus. Ellipticines with a quaternary methylpyridinium moiety were the most potent among all studied compounds, with MIC values as low as 2 mg/L in strains with intact efflux mechanisms. Antimicrobial activity of the studied compounds was connected to membrane damage, making their development as antibacterial drug candidates unlikely unless analogues devoid of this nonspecific effect can be discovered. (C) 2011 Elsevier Ltd. All rights reserved.