8-chloro-N-(2-(dimethylamino)ethyl)-11-methyl-11H-pyrido[3,2-a]carbazole-5-carboxamide | 1449007-05-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-chloro-N-(2-(dimethylamino)ethyl)-11-methyl-11H-pyrido[3,2-a]carbazole-5-carboxamide
• 英文别名: 8-chloro-N-[2-(dimethylamino)ethyl]-11-methylpyrido[3,2-a]carbazole-5-carboxamide
• CAS: 1449007-05-9
• 化学式: C₂₁H₂₁ClN₄O
• 分子量: 380.877
• InChiKey: QMVIVABTXCRGFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-chloro-1-methyl-1H-indole-3-carbaldehyde 在 palladium diacetate 、 四氯化钛 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 calcium chloride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.42h， 生成 8-chloro-N-(2-(dimethylamino)ethyl)-11-methyl-11H-pyrido[3,2-a]carbazole-5-carboxamide
  参考文献：
  名称：

  Design and synthesis of pyrido[3,2-α]carbazole derivatives and their analogues as potent antitumour agents

  摘要：

  A series of pyrido[3,2-a]carbazole derivatives and their analogues have been prepared and evaluated for their antitumour activity against human lung cancer A549 cells and colon cancer HT29 cells. The intermediates 4a-4k are successfully synthesized from 1a-1k and ethyl 2-(3-bromopyridin-2-yl)acetate by Knoevenagel condensation and intramolecular Heck-type reaction, and this is a novel and efficient synthetic approach to the core scaffold of the target compounds. These target compounds have shown an interesting antitumour profile towards the tested cell lines with IC50 values ranging from 0.07 mu M to 4.45 mu M. Among all the compounds synthesized, 8 compounds show higher potency than R16, 12 compounds are as potent as R16, and 6 compounds are less potent than R16. The best compound 24 is 7 times and approximately 10 times as potent as R16 against A549 and HT29 cells, respectively. (c) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.045

文献信息

• Design and synthesis of pyrido[3,2-α]carbazole derivatives and their analogues as potent antitumour agents
  作者：Bo Li、Zhi-Zhou Yue、Jian-Ming Feng、Qian He、Ze-Hong Miao、Chun-Hao Yang

  DOI：10.1016/j.ejmech.2013.05.045

  日期：2013.8

  A series of pyrido[3,2-a]carbazole derivatives and their analogues have been prepared and evaluated for their antitumour activity against human lung cancer A549 cells and colon cancer HT29 cells. The intermediates 4a-4k are successfully synthesized from 1a-1k and ethyl 2-(3-bromopyridin-2-yl)acetate by Knoevenagel condensation and intramolecular Heck-type reaction, and this is a novel and efficient synthetic approach to the core scaffold of the target compounds. These target compounds have shown an interesting antitumour profile towards the tested cell lines with IC50 values ranging from 0.07 mu M to 4.45 mu M. Among all the compounds synthesized, 8 compounds show higher potency than R16, 12 compounds are as potent as R16, and 6 compounds are less potent than R16. The best compound 24 is 7 times and approximately 10 times as potent as R16 against A549 and HT29 cells, respectively. (c) 2013 Elsevier Masson SAS. All rights reserved.