2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide | 66604-68-0

• 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: 2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
• 英文别名: 2-methyl-ellipticin-2-ium iodide；2-methylellipticinium iodide；2,5,11-trimethyl-6H-pyrido[4,3-b]carbazolium; iodide；2,5,11-Trimethyl-6H-pyrido[4,3-b]carbazolium; Jodid；2,5,11-Trimethyl-2H-pyrido[4,3-b]carbazole--hydrogen iodide (1/1)；2,5,11-trimethylpyrido[4,3-b]carbazole;hydroiodide
• CAS: 66604-68-0
• 化学式: C₁₈H₁₇N₂*I
• 分子量: 388.251
• InChiKey: IEBAEDRKJIAQLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 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：
  19.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide 在 sodium triphenoxide 作用下， 以 二甲基亚砜 为溶剂， 以91%的产率得到椭圆玫瑰树碱
  参考文献：
  名称：

  玫瑰树碱的合成

  摘要：

  6H-吡啶并[4,3-b]咔唑系统是通过酯烯酸酯对未活化吡啶鎓盐的分子内攻击而有效合成的。

  DOI：

  10.1016/s0040-4039(01)81172-2
• 作为产物：
  描述：

  1,4-二甲基-9H-咔唑 在 sodium carbonate 、 对甲苯磺酰氯 、 三氯氧磷 作用下， 以 四氢呋喃 、 水 、 邻二氯苯 、 丙酮 为溶剂， 反应 71.5h， 生成 2,5,11-trimethyl-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

文献信息

• Synthesis and Cytotoxicity of Novel Bis-Ellipticines and Bis-Isoellipticines
  作者：Gordon W. Gribble、Judy A. Obaza-Nutaitis

  DOI：10.3987/com-18-s(f)6

  日期：——
• Synthesis and in vitro antitumor activity of novel 2-alkyl-5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium and 2-alkylellipticin-2-ium chloride derivatives
  作者：Ryota Mori、Asako Kato、Kousuke Komenoi、Haruaki Kurasaki、Touru Iijima、Masashi Kawagoshi、Y.B. Kiran、Sho Takeda、Norio Sakai、Takeo Konakahara

  DOI：10.1016/j.ejmech.2014.05.032

  日期：2014.7

  Twenty-one types of novel ellipticine derivatives and pyridocarbazoles (5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazoles) with a nitrosourea moiety, linked by an oxydiethylene unit at the 2 position, were synthesized, and their cytotoxicity against HeLa S-3 cells was evaluated. Some of these new compounds exhibited potent antitumor activity by comparison with that of ellipticine. (C) 2014 Elsevier Masson SAS. All rights reserved.
• 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.
• Synthesis of ellipticine
  作者：Dwight D. Weller、Douglas W. Ford

  DOI：10.1016/s0040-4039(01)81172-2

  日期：1984.1

  The 6H-pyrido[4,3-b]carbazole system is efficiently synthesized by intramolecular attack of an ester enolate on an unactivated pyridinium salt.

  6H-吡啶并[4,3-b]咔唑系统是通过酯烯酸酯对未活化吡啶鎓盐的分子内攻击而有效合成的。