(3R,5S)-5-[(1R)-1-hydroxyethyl]pyrrolidin-3-ol | 216219-82-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3R,5S)-5-[(1R)-1-hydroxyethyl]pyrrolidin-3-ol
• CAS: 216219-82-8
• 化学式: C₆H₁₃NO₂
• 分子量: 131.175
• InChiKey: LGXFGGYOYSIDRG-PBXRRBTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,5S)-5-[(1R)-1-hydroxyethyl]pyrrolidin-3-ol 、 环丙基萘啶羧酸 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成 1-cyclopropyl-6-fluoro-7-[(2S,4R)-4-hydroxy-2-[(1R)-1-hydroxyethyl]pyrrolidin-1-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid
  参考文献：
  名称：

  The synthesis and biological evaluation of a novel series of C7 non-basic substituted fluoroquinolones as antibacterial agents

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2009.06.006
• 作为产物：
  描述：

  tert-butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-((R)-1-hydroxyethyl)pyrrolidine-1-carboxylate 在 水 、 三氟乙酸 作用下， 生成 (3R,5S)-5-[(1R)-1-hydroxyethyl]pyrrolidin-3-ol
  参考文献：
  名称：

  The synthesis and biological evaluation of a novel series of C7 non-basic substituted fluoroquinolones as antibacterial agents

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2009.06.006

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.