7-((3S)-3-amino-1-pyrrolidinyl)-1,4,-dihydro-1-(2,4-difluorophenyl)-6-fluoro-5-methyl-4-oxo-1,8-napthyridine-3-carboxylic acid | 132195-65-4

• 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-((3S)-3-amino-1-pyrrolidinyl)-1,4,-dihydro-1-(2,4-difluorophenyl)-6-fluoro-5-methyl-4-oxo-1,8-napthyridine-3-carboxylic acid
• 英文别名: 7-[(3S)-3-aminopyrrolidin-1-yl]-1-(2,4-difluorophenyl)-6-fluoro-5-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
• CAS: 132195-65-4
• 化学式: C₂₀H₁₇F₃N₄O₃
• 分子量: 418.375
• InChiKey: SKYPQEVVXGJKIJ-NSHDSACASA-N

物化性质

• 沸点：
  661.0±55.0 °C(Predicted)
• 密度：
  1.517±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)：
  0.7
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  99.8
• 氢给体数：
  2
• 氢受体数：
  10

安全信息

• 储存条件：
  -20°C，密闭保存，置于干燥处。

制备方法与用途

生物活性方面，BMY-43748 是一种高效的抗菌剂，不仅在体外显示出强烈的抗菌效果，在体内也同样表现优异。

反应信息

• 作为产物：
  描述：

  2,4-二氟苯胺 在 sodium hydroxide 、 sodium hydride 、 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 4.0h， 生成 7-((3S)-3-amino-1-pyrrolidinyl)-1,4,-dihydro-1-(2,4-difluorophenyl)-6-fluoro-5-methyl-4-oxo-1,8-napthyridine-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

• 5-Substituted-1,4-dihydro-4-oxonaphthyridine-3-carboxylate antibacterial agents
  申请人：Bristol-Myers Squibb Company

  公开号：EP0387802A2

  公开（公告）日：1990-09-19

  The invention is concerned with naphthyridine compounds of formula (I) which are substituted in the 7-position with various nitrogen heterocyclo groups and at the 1,3,4,5 and 6-positions with certain other groups. These compounds are antibacterial agents and are suitable for the treatment of infections.

  本发明涉及式（I）的萘啶化合物，该化合物在 7 位被各种氮杂环基团取代，在 1、3、4、5 和 6 位被某些其他基团取代。这些化合物是抗菌剂，适用于治疗感染。
• Naphthyridone carboxylic acid derivatives and antibacterial compositions containing them
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0544981A2

  公开（公告）日：1993-06-09

  The application comprises new compounds of the formula IV wherein R₂ is cyclopropyl or 2,4-difluorophenyl and Z is a group wherein R₅ and R₆ are each independently hydrogen and alkyl with 1 to 4 carbon atoms and n is an integer of from 0 to 4, a process of manufacture and pharmaceutical compositions useful as antibacterials.

  本申请包括式 IV 的新化合物 其中 R₂ 是环丙基或 2,4-二氟苯基，Z 是一个基团 其中R₅和R₆各自独立地为氢和含有1至4个碳原子的烷基，n为0至4的整数，该化合物的制造工艺和用作抗菌剂的药物组合物。
• US5585491A
  申请人：——

  公开号：US5585491A

  公开（公告）日：1996-12-17
• 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.