1-cyclopropyl-6-fluoro-7-((S)-2-hydroxymethylpyrrolidin-1-yl)-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid | 908340-57-8

• 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: 1-cyclopropyl-6-fluoro-7-((S)-2-hydroxymethylpyrrolidin-1-yl)-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid
• 英文别名: 1-cyclopropyl-6-fluoro-7-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid
• CAS: 908340-57-8
• 化学式: C₁₇H₁₈FN₃O₄
• 分子量: 347.346
• InChiKey: KQQBHABNKCZFAJ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  94
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-cyclopropyl-6-fluoro-7-((S)-2-hydroxymethylpyrrolidin-1-yl)-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到(15S)-7-cyclopropyl-4-oxo-17-oxa-7,9,11-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),2,5,8-tetraene-5-carboxylic acid
  参考文献：
  名称：

  Novel Antibacterial Class:  A Series of Tetracyclic Derivatives

  摘要：

  We describe the synthesis and antibacterial activity of a series of tetracyclic naphthyridones. The members of this series act primarily via inhibition of bacterial translation and belong to the class of novel ribosome inhibitors (NRIs). In this paper we explore the structure-activity relationships (SAR) of these compounds to measure their ability both to inhibit bacterial translation and also to inhibit the growth of bacterial cells in culture. The most active of these compounds inhibit Streptococcus pneumoniae translation at concentrations of < 5 mu M and have minimum inhibitory concentrations (MICs) of < 8 mu g/mL against clinically relevant strains of bacteria.

  DOI：

  10.1021/jm060010w
• 作为产物：
  描述：

  L-脯氨醇 在 lithium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 96.0h， 生成 1-cyclopropyl-6-fluoro-7-((S)-2-hydroxymethylpyrrolidin-1-yl)-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid
  参考文献：
  名称：

  Novel Antibacterial Class:  A Series of Tetracyclic Derivatives

  摘要：

  We describe the synthesis and antibacterial activity of a series of tetracyclic naphthyridones. The members of this series act primarily via inhibition of bacterial translation and belong to the class of novel ribosome inhibitors (NRIs). In this paper we explore the structure-activity relationships (SAR) of these compounds to measure their ability both to inhibit bacterial translation and also to inhibit the growth of bacterial cells in culture. The most active of these compounds inhibit Streptococcus pneumoniae translation at concentrations of < 5 mu M and have minimum inhibitory concentrations (MICs) of < 8 mu g/mL against clinically relevant strains of bacteria.

  DOI：

  10.1021/jm060010w

文献信息

• The synthesis and biological evaluation of a novel series of C7 non-basic substituted fluoroquinolones as antibacterial agents
  作者：Xiaoguang Huang、Dongliang Chen、Ning Wu、Aiqin Zhang、Zhenhua Jia、Xingshu Li

  DOI：10.1016/j.bmcl.2009.06.006

  日期：2009.8

  A series of non-basic building blocks was synthesized and introduced to the C7 position of the quinolone nucleus 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid to afford the corresponding. fluoroquinolones in 46-85% yield. The antibacterial activity of these new. fluoroquinolones was evaluated using a standard broth microdilution technique. The sulfur-containing quinolone, 7-(2-thia-5-azabicyclo[2.2.1]heptan-5-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid exhibited a superior antibacterial activity against quinolone-susceptible and multidrug-resistant strains in comparison with the clinically used fluoroquinolones ciprofloxacin and vancomycin, especially to the Streptococcus pneumonia and multidrug-resistant S. pneumonia clinical isolates. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.
• Novel Antibacterial Class:  A Series of Tetracyclic Derivatives
  作者：Mira M. Hinman、Teresa A. Rosenberg、Darlene Balli、Candace Black-Schaefer、Linda E. Chovan、Douglas Kalvin、Philip J. Merta、Angela M. Nilius、Steve D. Pratt、Niru B. Soni、Frank L. Wagenaar、Moshe Weitzberg、Rolf Wagner、Bruce A. Beutel

  DOI：10.1021/jm060010w

  日期：2006.8.1

  We describe the synthesis and antibacterial activity of a series of tetracyclic naphthyridones. The members of this series act primarily via inhibition of bacterial translation and belong to the class of novel ribosome inhibitors (NRIs). In this paper we explore the structure-activity relationships (SAR) of these compounds to measure their ability both to inhibit bacterial translation and also to inhibit the growth of bacterial cells in culture. The most active of these compounds inhibit Streptococcus pneumoniae translation at concentrations of < 5 mu M and have minimum inhibitory concentrations (MICs) of < 8 mu g/mL against clinically relevant strains of bacteria.