6-ethyl-3-phenyl-5-tosyl-pyrrolo[3,4-c]pyrano[5,6-b]quinol-7-one

• 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: 6-ethyl-3-phenyl-5-tosyl-pyrrolo[3,4-c]pyrano[5,6-b]quinol-7-one
• 英文别名: (11R,15S)-12-ethyl-2-methyl-13-(4-methylphenyl)sulfonyl-16-phenyl-17-oxa-2,13-diazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3,5,7-tetraen-9-one
• 化学式: C₃₀H₃₀N₂O₄S
• 分子量: 514.645
• InChiKey: JBVCFYFACRINMU-KKLSKWOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  75.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-羟基-N-甲基-2-喹啉 、 4-methyl-N-(1-oxobutan-2-yl)-N-(3-phenylallyl)benzenesulfonamide 在 ethylenediamine Tetraacetic Acid 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以50%的产率得到3-ethyl-6-phenyl-4-tosyl-pyrrolo[3,4-c]pyrano[5,6-c]quinol-2-one
  参考文献：
  名称：

  Synthesis and antibacterial property of pyrrolopyrano quinolinones and pyrroloquinolines

  摘要：

  Synthesis of a series of novel pyrroloquinolinone and pyrroloquinoline derivatives has been accomplished by intramolecular domino Knoevenagel hetero Diels-Alder reaction and intramolecular imino Diels-Alder reaction. These compounds were evaluated for their antibacterial activity against bacterial pathogens using disc diffusion and broth dilution methods. The efficacy of binding of these compounds to gyrase, an enzyme known to play a key role in bacterial replication is examined by studying its supercoiling and relaxation and also its gene expression using PCR method. The results indicated that most of the synthesised compounds exhibited good antibacterial activity against the microorganisms with MIC values of 5 mM and could inhibit gyrase effectively leading to cell death. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.060

文献信息

• Synthesis and antibacterial property of pyrrolopyrano quinolinones and pyrroloquinolines
  作者：Mathesan Jayagobi、Ragavachary Raghunathan、Shilpakala Sainath、Malathi Raghunathan

  DOI：10.1016/j.ejmech.2011.02.060

  日期：2011.6

  Synthesis of a series of novel pyrroloquinolinone and pyrroloquinoline derivatives has been accomplished by intramolecular domino Knoevenagel hetero Diels-Alder reaction and intramolecular imino Diels-Alder reaction. These compounds were evaluated for their antibacterial activity against bacterial pathogens using disc diffusion and broth dilution methods. The efficacy of binding of these compounds to gyrase, an enzyme known to play a key role in bacterial replication is examined by studying its supercoiling and relaxation and also its gene expression using PCR method. The results indicated that most of the synthesised compounds exhibited good antibacterial activity against the microorganisms with MIC values of 5 mM and could inhibit gyrase effectively leading to cell death. (C) 2011 Elsevier Masson SAS. All rights reserved.