N-butyl-9-bromo-5,12-dioxo-5,12-dihydroindolizino[2,3-g]quinoline-6-carboxamide | 1335015-09-2

• 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: N-butyl-9-bromo-5,12-dioxo-5,12-dihydroindolizino[2,3-g]quinoline-6-carboxamide
• 英文别名: 9-bromo-N-butyl-5,12-dioxoindolizino[2,3-g]quinoline-6-carboxamide
• CAS: 1335015-09-2
• 化学式: C₂₀H₁₆BrN₃O₃
• 分子量: 426.269
• InChiKey: ZZSCZWZRDJZCQB-UHFFFAOYSA-N

物化性质

• 熔点：
  264.8-267.1 °C
• 密度：
  1.61±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  80.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6,7-二氯-5,8-喹啉二酮 在 4-二甲氨基吡啶 、 氯化亚砜 、 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 氯仿 、 水 、 异丙醇 为溶剂， 反应 39.0h， 生成 N-butyl-9-bromo-5,12-dioxo-5,12-dihydroindolizino[2,3-g]quinoline-6-carboxamide
  参考文献：
  名称：

  Synthesis, antimicrobial activity and possible mechanism of action of 9-bromo-substituted indolizinoquinoline-5,12-dione derivatives

  摘要：

  A series of 9-bromo-substituted indolizinoquinoline-5,12-dione derivatives was synthesized. Antimicrobial activity assessment indicates that compounds 1, 26, 27 and 28 exhibit strong activity against gram-positive bacterial strains, including Beta-hemolytic streptococcus CMCC32210, Staphylococcus aureus ATCC25923, Staphylococcus epidermidis ATCC12228, Enterococcus faecalis ATCC29212 and methicillin-resistant S. aureus ATCC43300 (MRSA). Compound 27 shows the best anti-MRSA activity with an MIC value of 0.031 mu g/ml. To assess the mechanism of action, the inhibitory activities of compound 1 against DNA gyrase and DNA topoisomerase IV were also measured. The results indicate that compound 1 has strong inhibitory effects on the Escherichia coli DNA gyrase supercoiling activity and S. aureus Topo IV relaxing activity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.042

文献信息

• Synthesis, antimicrobial activity and possible mechanism of action of 9-bromo-substituted indolizinoquinoline-5,12-dione derivatives
  作者：Xi-Wei Wu、Zu-Ping Wu、Lu-Xia Wang、Hong-Bin Zhang、Jian-Wen Chen、Wei Zhang、Lian-Quan Gu、Zhi-Shu Huang、Lin-Kun An

  DOI：10.1016/j.ejmech.2011.07.042

  日期：2011.9

  A series of 9-bromo-substituted indolizinoquinoline-5,12-dione derivatives was synthesized. Antimicrobial activity assessment indicates that compounds 1, 26, 27 and 28 exhibit strong activity against gram-positive bacterial strains, including Beta-hemolytic streptococcus CMCC32210, Staphylococcus aureus ATCC25923, Staphylococcus epidermidis ATCC12228, Enterococcus faecalis ATCC29212 and methicillin-resistant S. aureus ATCC43300 (MRSA). Compound 27 shows the best anti-MRSA activity with an MIC value of 0.031 mu g/ml. To assess the mechanism of action, the inhibitory activities of compound 1 against DNA gyrase and DNA topoisomerase IV were also measured. The results indicate that compound 1 has strong inhibitory effects on the Escherichia coli DNA gyrase supercoiling activity and S. aureus Topo IV relaxing activity. (C) 2011 Elsevier Masson SAS. All rights reserved.