9-bromo-5,12-dioxo-5,12-dihydroindolizino[2,3-g]quinoline-6-carboxylic acid | 1335014-85-1

• 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: 9-bromo-5,12-dioxo-5,12-dihydroindolizino[2,3-g]quinoline-6-carboxylic acid
• 英文别名: 9-Bromo-5,12-dioxoindolizino[2,3-g]quinoline-6-carboxylic acid
• CAS: 1335014-85-1
• 化学式: C₁₆H₇BrN₂O₄
• 分子量: 371.147
• InChiKey: VZJMGRCVRNJLMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-bromo-5,12-dioxo-5,12-dihydroindolizino[2,3-g]quinoline-6-carboxylic acid 在 4-二甲氨基吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 10.0h， 生成 2-fluoroethyl 9-bromo-5,12-dioxo-5,12-dihydroindolizino[2,3-g]quinoline-6-carboxylate
  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
• 作为产物：
  描述：

  3-溴吡啶 在 potassium carbonate 作用下， 以 乙醇 、 水 、 异丙醇 为溶剂， 反应 29.0h， 生成 9-bromo-5,12-dioxo-5,12-dihydroindolizino[2,3-g]quinoline-6-carboxylic acid
  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

• Syntheses and antibacterial activity of soluble 9-bromo substituted indolizinoquinoline-5,12-dione derivatives
  作者：Hui Yang、Hao-Wen Wang、Teng-Wei Zhu、Le-Mao Yu、Jian-Wen Chen、Lu-Xia Wang、Lei Shi、Ding Li、Lian-Quan Gu、Zhi-Shu Huang、Lin-Kun An

  DOI：10.1016/j.ejmech.2016.12.054

  日期：2017.2

  low bioavailability in vivo possibly due to its low solubility in water. In order to obtain the derivatives with higher anti-MRSA activity and good water solubility, twenty eight bromo-substituted indolizinoquinoline-5,12-dione derivatives were synthesized in the present study. The antibacterial activity of the synthesized compounds was evaluated against one gram-negative and some gram-positive bacterial

  在我们之前的研究中，发现9-溴吲哚并喹啉-5,12-二酮1是一种良好的抗MRSA药物。然而，由于其在水中的低溶解度，它在体内的生物利用度非常低。为了获得具有较高的抗MRSA活性和良好的水溶性的衍生物，本研究合成了28个溴取代的吲哚并喹啉-5，12-二酮衍生物。评估了合成化合物对一种革兰氏阴性和某些革兰氏阳性细菌菌株（包括100株临床MRSA菌株）的抗菌活性。的UV测定法进行，以确定六个活性化合物的溶解度16，21，23和27-29。最有效的化合物28表现出对临床MRSA菌株的强活性，MIC 50和MIC 90值均低于7.8 ng / mL。化合物27具有1.98 mg / mL的良好水溶性，并且对临床MRSA菌株具有很强的活性，MIC 50值为63 ng / mL，MIC 90值为125 ng / mL，比万古霉素高16倍。