7-<4-(2-aminoethyl)-1-piperazinyl>-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid | 99726-80-4

• 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: 7-<4-(2-aminoethyl)-1-piperazinyl>-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
• 英文别名: 7-[4-(2-Aminoethyl)piperazin-1-yl]-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
• CAS: 99726-80-4
• 化学式: C₁₈H₂₃FN₄O₃
• 分子量: 362.404
• InChiKey: IGDMJKDTMJLSLX-UHFFFAOYSA-N

物化性质

• 沸点：
  580.4±50.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  90.1
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  诺氟沙星 在 钴 氢气 、 三乙胺 作用下， 以 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 25.0~100.0 ℃ 、10.34 MPa 条件下， 反应 12.0h， 生成 7-<4-(2-aminoethyl)-1-piperazinyl>-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
  参考文献：
  名称：

  New structure-activity relationships of the quinolone antibacterials using the target enzyme. The development and application of a DNA gyrase assay

  摘要：

  A series of 60 newly synthesized and known quinolone antibacterials, including quinoline- and 1,8-naphthyridine-3-carboxylic acids, pyrido[2,3-d]pyrimidine-6-carboxylic acids, and some monocyclic 4-pyridone-3-carboxylic acids, were tested and compared in a newly established, easy to perform, DNA gyrase assay. The results were correlated with minimum inhibitory concentrations (MICs) against a variety of organisms. Among the known quinolones were 14 clinically significant drugs (oxolinic acid, norfloxacin, ciprofloxacin, enoxacin, etc.) which were used as standards and compared side-by-side. The study focused on the changes in DNA gyrase inhibition brought about by certain features of the molecules, namely, the C6-fluorine or the nature of the C7 substituent. The intrinsic gyrase inhibition of the fused parent rings, quinoline vs. naphthyridine vs. pyrido[2,3-d]pyrimidine, was also explored. In all cases, loss of enzyme inhibition produced poor MICs, but some compounds with good DNA gyrase inhibition did not correspondingly inhibit bacterial growth. Possible explanations for this phenomena and the benefits of a DNA gyrase-MIC strategy for developing future structure-activity relationships are discussed.

  DOI：

  10.1021/jm00153a015

文献信息

• New structure-activity relationships of the quinolone antibacterials using the target enzyme. The development and application of a DNA gyrase assay
  作者：John M. Domagala、Lori Doyle Hanna、Carl L. Heifetz、Marland P. Hutt、Thomas F. Mich、Joseph P. Sanchez、Marjorie Solomon

  DOI：10.1021/jm00153a015

  日期：1986.3

  A series of 60 newly synthesized and known quinolone antibacterials, including quinoline- and 1,8-naphthyridine-3-carboxylic acids, pyrido[2,3-d]pyrimidine-6-carboxylic acids, and some monocyclic 4-pyridone-3-carboxylic acids, were tested and compared in a newly established, easy to perform, DNA gyrase assay. The results were correlated with minimum inhibitory concentrations (MICs) against a variety of organisms. Among the known quinolones were 14 clinically significant drugs (oxolinic acid, norfloxacin, ciprofloxacin, enoxacin, etc.) which were used as standards and compared side-by-side. The study focused on the changes in DNA gyrase inhibition brought about by certain features of the molecules, namely, the C6-fluorine or the nature of the C7 substituent. The intrinsic gyrase inhibition of the fused parent rings, quinoline vs. naphthyridine vs. pyrido[2,3-d]pyrimidine, was also explored. In all cases, loss of enzyme inhibition produced poor MICs, but some compounds with good DNA gyrase inhibition did not correspondingly inhibit bacterial growth. Possible explanations for this phenomena and the benefits of a DNA gyrase-MIC strategy for developing future structure-activity relationships are discussed.