1-Cyclopropyl-7-((3R,5S)-3,5-dimethyl-piperazin-1-yl)-8-methyl-6-nitro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester | 1027076-50-1

• 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: 1-Cyclopropyl-7-((3R,5S)-3,5-dimethyl-piperazin-1-yl)-8-methyl-6-nitro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 1-cyclopropyl-7-[(3S,5R)-3,5-dimethylpiperazin-1-yl]-8-methyl-6-nitro-4-oxoquinoline-3-carboxylate
• CAS: 1027076-50-1
• 化学式: C₂₂H₂₈N₄O₅
• 分子量: 428.488
• InChiKey: IHTFQKWLIVRXKK-BETUJISGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-Cyclopropyl-7-((3R,5S)-3,5-dimethyl-piperazin-1-yl)-8-methyl-6-nitro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 在 镍 氢气 作用下， 以 乙二醇甲醚 为溶剂， 反应 1.0h， 生成 6-Amino-1-cyclopropyl-7-((3R,5S)-3,5-dimethyl-piperazin-1-yl)-8-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester
  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
• 作为产物：
  描述：

  2-chloro-4-fluoro-3-methyl-5-nitrobenzoyl chloride 在 potassium carbonate 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 26.92h， 生成 1-Cyclopropyl-7-((3R,5S)-3,5-dimethyl-piperazin-1-yl)-8-methyl-6-nitro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester
  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