7-((S)-3-Amino-pyrrolidin-1-yl)-6-fluoro-1-(2-fluoro-1,1-dimethyl-ethyl)-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid | 138668-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7-((S)-3-Amino-pyrrolidin-1-yl)-6-fluoro-1-(2-fluoro-1,1-dimethyl-ethyl)-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid
• 英文别名: 7-[(3S)-3-aminopyrrolidin-1-yl]-6-fluoro-1-(2-fluoro-1,1-dimethyl-ethyl)-5-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid；7-[(3S)-3-aminopyrrolidin-1-yl]-6-fluoro-1-(1-fluoro-2-methylpropan-2-yl)-5-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
• CAS: 138668-39-0
• 化学式: C₁₈H₂₂F₂N₄O₃
• 分子量: 380.394
• InChiKey: URMPNTFAJSVTGR-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.8
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2,6-二氯-5-氟烟酸 在 sodium hydroxide 、 五氯化磷 、 甲基锂 、 乙酸酐 、 sodium hydride 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 、 乙醇 、 乙腈 为溶剂， 反应 27.63h， 生成 7-((S)-3-Amino-pyrrolidin-1-yl)-6-fluoro-1-(2-fluoro-1,1-dimethyl-ethyl)-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid
  参考文献：
  名称：

  Fluoronaphthyridines as antibacterial agents. 4. Synthesis and structure-activity relationships of 5-substituted 6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids

  摘要：

  A series of 5-substituted-6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids have been prepared and tested for their in vitro and in vivo antibacterial activities. The 5-methyl group gave better in vitro activity with the 1-cyclopropyl appendage, but poorer activity with the 1-tert-butyl moiety. With the 1-(2,4-difluorophenyl) substitution, the influence of the 7-cycloalkylamino group was determinant: a (3S)-3-amino-pyrrolidine was shown to enhance greatly the in vitro and in vivo activity of the 5-methyl derivative. Compound 33 (BMY 43748) was selected as a promising candidate for an improved therapeutic agent.

  DOI：

  10.1021/jm00081a013

文献信息

• Fluoronaphthyridines as antibacterial agents. 4. Synthesis and structure-activity relationships of 5-substituted 6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids
  作者：D. Bouzard、P. Di Cesare、M. Essiz、J. P. Jacquet、B. Ledoussal、P. Remuzon、R. E. Kessler、J. Fung-Tomc

  DOI：10.1021/jm00081a013

  日期：1992.2

  A series of 5-substituted-6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids have been prepared and tested for their in vitro and in vivo antibacterial activities. The 5-methyl group gave better in vitro activity with the 1-cyclopropyl appendage, but poorer activity with the 1-tert-butyl moiety. With the 1-(2,4-difluorophenyl) substitution, the influence of the 7-cycloalkylamino group was determinant: a (3S)-3-amino-pyrrolidine was shown to enhance greatly the in vitro and in vivo activity of the 5-methyl derivative. Compound 33 (BMY 43748) was selected as a promising candidate for an improved therapeutic agent.