9-bromo-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole | 69492-81-5

• 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-bromo-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole
• 英文别名: 9-Bromo-5,6,11-trimethylpyrido[4,3-b]carbazole
• CAS: 69492-81-5
• 化学式: C₁₈H₁₅BrN₂
• 分子量: 339.234
• InChiKey: NLSUJHPLOGTMNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-bromo-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole 、 碘甲烷 以 丙酮 为溶剂， 反应 48.0h， 以57%的产率得到9-bromo-2,5,6,11-tetramethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
  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：

  6-bromo-1,4-dimethyl-9H-carbazole 在 sodium hydride 、 sodium carbonate 、 对甲苯磺酰氯 、 三氯氧磷 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 邻二氯苯 为溶剂， 反应 24.0h， 生成 9-bromo-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole
  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

文献信息

• 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.