4-methyl-2-(4-nitrophenyl)-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione | 1608483-63-1

• 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: 4-methyl-2-(4-nitrophenyl)-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione
• 英文别名: 4-Methyl-2-(4-nitrophenyl)pyrrolo[3,4-c]quinoline-1,3-dione
• CAS: 1608483-63-1
• 化学式: C₁₈H₁₁N₃O₄
• 分子量: 333.303
• InChiKey: HJOVAZVAWIYLCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  96.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙酰乙酰对硝基苯胺 、 靛红 在 1-butyl-3-methylimidazolium Tetrafluoroborate 作用下， 以 甲苯 为溶剂， 反应 0.67h， 以48%的产率得到4-methyl-2-(4-nitrophenyl)-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione
  参考文献：
  名称：

  Microwave-Assisted Synthesis of Diverse Pyrrolo[3,4-c]quinoline-1,3-diones and Their Antibacterial Activities

  摘要：

  With the aim of developing a general and practical method for library production, a novel and efficient two-phase microwave-assisted cascade reaction between isatins and beta-ketoamides in [Bmim]BF4/toluene was developed for the synthesis of pyrrolo[3,4-c]quinoline-1,3-diones. The features of this methodology are, the use of microwave-assisted rapid synthesis, mild reaction conditions, high yields, operational simplicity, facile product separation, and recyclability. Furthermore, the antibacterial activities of the pyrrolo[3,4-c]quinoline-1,3-dione derivatives produced were evaluated against Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa, and Enterobacter aerogenes) and Gram-positive bacteria (Bacillus cereus and Staphylococcus aureus). These derivatives showed antibacterial activities against Gram-positive strains that were at least equivalent to that against Gram-negative strains. Compound 7{3,5} displayed the most potent antibacterial activity against P. aeruginosa (MIC = 0.5 mu g/mL) and greater activity than standard ampicillin (MIC = 1 mu g/mL). Compound 7{4,7} exhibited the best inhibitory activity against E. coli and E. aerogenes (MIC = 1 and 0.5 mu g/mL), compared with the standard ampicillin (both MICs = 1 mu g/mL). The synthesized pyrrolo[3,4-c]quinoline-1,3-diones are expected to be widely used as lead compounds for the development of new antibacterial agents.

  DOI：

  10.1021/co500002s