1-cyclopropyl-6-fluoro-1,4-dihydro-7-[4-{5-(2-oxo-2-(p-tolyl)ethylthio)-1,3,4-thiadiazol-2-yl}piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid | 1378026-86-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-cyclopropyl-6-fluoro-1,4-dihydro-7-[4-{5-(2-oxo-2-(p-tolyl)ethylthio)-1,3,4-thiadiazol-2-yl}piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
• 英文别名: 1-Cyclopropyl-6-fluoro-7-[4-[5-[2-(4-methylphenyl)-2-oxoethyl]sulfanyl-1,3,4-thiadiazol-2-yl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid；1-cyclopropyl-6-fluoro-7-[4-[5-[2-(4-methylphenyl)-2-oxoethyl]sulfanyl-1,3,4-thiadiazol-2-yl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
• CAS: 1378026-86-8
• 化学式: C₂₈H₂₆FN₅O₄S₂
• 分子量: 579.676
• InChiKey: ZAQQOSDWHFKPCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  2-[(5-Amino-1,3,4-thiadiazol-2-yl)sulfanyl]-1-(4-methylphenyl)ethanone 在 盐酸 、 铜 、 碳酸氢钠 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 1-cyclopropyl-6-fluoro-1,4-dihydro-7-[4-{5-(2-oxo-2-(p-tolyl)ethylthio)-1,3,4-thiadiazol-2-yl}piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and antibacterial, antimycobacterial and docking studies of novel N-piperazinyl fluoroquinolones

  摘要：

  The present study deals with the synthesis of some novel fluoroquinolone derivatives as antibacterial and antitubercular agents. The titled compounds 7a-g and 8a-g were found to possess comparable or more potent activity than the reference compounds ciprofloxacin, norfloxacin, isoniazid and rifampicin. The synthesized compounds showed activity against S. aureus and C. bacterium, whereas poor activity was observed against P. aeruginosa and E. coli. These compounds were subjected to in vitro cytotoxicity study by MTT assay, and their selectivity index was calculated. Compound 7d was found to be the most efficient antimycobacterial agent amongst the series. Molecular docking revealed that synthesized derivatives and target proteins were actively involved in a binding pattern and had significant correlation with biological activity.Novel N-piperazinyl fluoroquinolone derivatives were synthesized and evaluated for their in vitro antibacterial, antimycobacterial and cytotoxic properties. Activity results were compared with the docking results.

  DOI：

  10.1007/s00044-012-0074-2

文献信息

• Synthesis and antibacterial, antimycobacterial and docking studies of novel N-piperazinyl fluoroquinolones
  作者：Kapil M. Agrawal、Gokul S. Talele

  DOI：10.1007/s00044-012-0074-2

  日期：2013.2

  The present study deals with the synthesis of some novel fluoroquinolone derivatives as antibacterial and antitubercular agents. The titled compounds 7a-g and 8a-g were found to possess comparable or more potent activity than the reference compounds ciprofloxacin, norfloxacin, isoniazid and rifampicin. The synthesized compounds showed activity against S. aureus and C. bacterium, whereas poor activity was observed against P. aeruginosa and E. coli. These compounds were subjected to in vitro cytotoxicity study by MTT assay, and their selectivity index was calculated. Compound 7d was found to be the most efficient antimycobacterial agent amongst the series. Molecular docking revealed that synthesized derivatives and target proteins were actively involved in a binding pattern and had significant correlation with biological activity.Novel N-piperazinyl fluoroquinolone derivatives were synthesized and evaluated for their in vitro antibacterial, antimycobacterial and cytotoxic properties. Activity results were compared with the docking results.