MF5137 | 148927-23-5

• 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: MF5137
• 英文别名: 6-amino-1-cyclopropyl-7-(3,4-dihydro-1H-isoquinolin-2-yl)-8-methyl-4-oxoquinoline-3-carboxylic acid
• CAS: 148927-23-5
• 化学式: C₂₃H₂₃N₃O₃
• 分子量: 389.454
• InChiKey: LLVLMYRWABCVEU-UHFFFAOYSA-N

物化性质

• 沸点：
  681.8±55.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  86.9
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 储存条件：
  2-8℃

制备方法与用途

生物活性

MF 5137 是一种有效的抗菌剂。

靶点

• 抗菌

体外研究

• MF 5137（化合物2）在UVA照射下迅速光解，产生有毒的光产物。经过15分钟照射后，MF 5137使蛋白质发光减少约80%。这一效应在厌氧条件下显著减弱。

反应信息

• 作为产物：
  描述：

  1-Cyclopropyl-7-fluoro-8-methyl-6-nitro-4-oxoquinoline-3-carboxylic acid 在 镍 氢气 、 三乙胺 作用下， 以 乙二醇甲醚 、 乙腈 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 41.0h， 生成 MF5137
  参考文献：
  名称：

  Studies on 6-Aminoquinolones:  Synthesis and Antibacterial Evaluation of 6-Amino-8-methylquinolones

  摘要：

  The 6-aminoquinolone had previously been identified as a new class of quinolone antibacterial agents. To continue our structure-activity relationship (SAR) study in this series, novel 6-amino-8-methylquinolone derivatives have now been synthesized and evaluated for in vitro antibacterial activity. We have shown that the coupled presence of a methyl group at the C-8 position with an amino group at C-6 is effective for enhancing antibacterial activity, particularly against Gram-positive bacteria. The SARs associated with the N-1, C-6, and C-7 are discussed. The 1,2,3,4-tetrahydroisoquinolinyl derivative 19v showed the highest antibacterial activity with MIC values on Gram-positive bacteria superior to that of ciprofloxacin, especially against Staphylococcus aureus strains, including those strains which are methicillin- and ciprofloxacin-resistant.

  DOI：

  10.1021/jm950558v

文献信息

• Studies on 6-Aminoquinolones:  Synthesis and Antibacterial Evaluation of 6-Amino-8-methylquinolones
  作者：Violetta Cecchetti、Arnaldo Fravolini、Maria Cristina Lorenzini、Oriana Tabarrini、Patrizia Terni、Tao Xin

  DOI：10.1021/jm950558v

  日期：1996.1.1

  The 6-aminoquinolone had previously been identified as a new class of quinolone antibacterial agents. To continue our structure-activity relationship (SAR) study in this series, novel 6-amino-8-methylquinolone derivatives have now been synthesized and evaluated for in vitro antibacterial activity. We have shown that the coupled presence of a methyl group at the C-8 position with an amino group at C-6 is effective for enhancing antibacterial activity, particularly against Gram-positive bacteria. The SARs associated with the N-1, C-6, and C-7 are discussed. The 1,2,3,4-tetrahydroisoquinolinyl derivative 19v showed the highest antibacterial activity with MIC values on Gram-positive bacteria superior to that of ciprofloxacin, especially against Staphylococcus aureus strains, including those strains which are methicillin- and ciprofloxacin-resistant.