1-cyclopropyl-6-fluoro-7-(4-(2-hydroxy-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propyl)-3-methylpiperazin-1-yl)-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

• 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: 1-cyclopropyl-6-fluoro-7-(4-(2-hydroxy-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propyl)-3-methylpiperazin-1-yl)-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 1-Cyclopropyl-6-fluoro-7-[4-[2-hydroxy-3-(2-methyl-5-nitroimidazol-1-yl)propyl]-3-methylpiperazin-1-yl]-8-methoxy-4-oxoquinoline-3-carboxylic acid；1-cyclopropyl-6-fluoro-7-[4-[2-hydroxy-3-(2-methyl-5-nitroimidazol-1-yl)propyl]-3-methylpiperazin-1-yl]-8-methoxy-4-oxoquinoline-3-carboxylic acid
• 化学式: C₂₆H₃₁FN₆O₇
• 分子量: 558.567
• InChiKey: JUZUITZGVRDHEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  157
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  奥硝唑 、 加替沙星 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以93%的产率得到1-cyclopropyl-6-fluoro-7-(4-(2-hydroxy-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propyl)-3-methylpiperazin-1-yl)-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Design, Synthesis, Antibacterial Evaluation and Docking Study of Novel 2-Hydroxy-3-(nitroimidazolyl)-propyl-derived Quinolone

  摘要：

  A novel series of 2‐hydroxy‐3‐(nitroimidazolyl)‐propyl‐derived quinolones 6a–o were synthesized and evaluated for their in vitro antibacterial activity. Most of the target compounds exhibited potent activity against Gram‐positive strains. Among them, moxifloxacin analog 6n displayed the most potent activity against Gram‐positive strains including S. epidermidis (MIC = 0.06 μg/mL), MSSE (MIC = 0.125 μg/mL), MRSE (MIC = 0.03 μg/mL), S. aureus (MIC = 0.125 μg/mL), MSSA (MIC = 0.125 μg/mL), (MIC = 2 μg/mL). Its activity against MRSA was eightfold more potent than reference drug gatifloxacin. Finally, docking study of the target compound 6n revealed that the binding model of quinolone nucleus was similar to that of gatifloxacin and the 2‐hydroxy‐3‐(nitroimidazolyl)‐propyl group formed two additional hydrogen bonds.

  DOI：

  10.1111/cbdd.12395

文献信息

• Design, Synthesis, Antibacterial Evaluation and Docking Study of Novel 2-Hydroxy-3-(nitroimidazolyl)-propyl-derived Quinolone
  作者：Qing Li、Junhao Xing、Haibo Cheng、Hui Wang、Jing Wang、Shuai Wang、Jinpei Zhou、Huibin Zhang

  DOI：10.1111/cbdd.12395

  日期：2015.1

  A novel series of 2‐hydroxy‐3‐(nitroimidazolyl)‐propyl‐derived quinolones 6a–o were synthesized and evaluated for their in vitro antibacterial activity. Most of the target compounds exhibited potent activity against Gram‐positive strains. Among them, moxifloxacin analog 6n displayed the most potent activity against Gram‐positive strains including S. epidermidis (MIC = 0.06 μg/mL), MSSE (MIC = 0.125 μg/mL), MRSE (MIC = 0.03 μg/mL), S. aureus (MIC = 0.125 μg/mL), MSSA (MIC = 0.125 μg/mL), (MIC = 2 μg/mL). Its activity against MRSA was eightfold more potent than reference drug gatifloxacin. Finally, docking study of the target compound 6n revealed that the binding model of quinolone nucleus was similar to that of gatifloxacin and the 2‐hydroxy‐3‐(nitroimidazolyl)‐propyl group formed two additional hydrogen bonds.