N-(((5S)-3-(3-fluoro-4-(5-(methoxyimino)hexahydrocyclopenta[c]pyrrol-2(1H)-yl)phenyl)-2-oxo-oxazolidin-5-yl)methyl)acetamide | 1395322-98-1

• 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: N-(((5S)-3-(3-fluoro-4-(5-(methoxyimino)hexahydrocyclopenta[c]pyrrol-2(1H)-yl)phenyl)-2-oxo-oxazolidin-5-yl)methyl)acetamide
• 英文别名: N-[[(5S)-3-[3-fluoro-4-(5-methoxyimino-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl)phenyl]-2-oxo-oxazolidin-5-yl]methyl]acetamide；N-[[(5S)-3-[3-fluoro-4-(5-methoxyimino-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
• CAS: 1395322-98-1
• 化学式: C₂₀H₂₅FN₄O₄
• 分子量: 404.441
• InChiKey: JUHNZOHFLPCFDF-KVULBXGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  29
• 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：
  83.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (5R)-5-(azidomethyl)-3-(3-fluoro-4-(tetrahydro-1H-spiro[cyclopenta[c]pyrrole-5,2'-[1,3]dioxolane]-2(3H)-yl)phenyl)-oxazolidin-2-one 在 吡啶 、 palladium 10% on activated carbon 、 盐酸羟胺 、 氢气 、 碳酸氢钠 、 对甲苯磺酸 作用下， 以 乙醇 、 水 、 乙酸乙酯 、 丙酮 为溶剂， 反应 78.0h， 生成 N-(((5S)-3-(3-fluoro-4-(5-(methoxyimino)hexahydrocyclopenta[c]pyrrol-2(1H)-yl)phenyl)-2-oxo-oxazolidin-5-yl)methyl)acetamide
  参考文献：
  名称：

  Synthesis and In Vitro Antibacterial Activity of Novel 3-Azabicyclo[3.3.0]octanyl Oxazolidinones

  摘要：

  We synthesized a series of oxazolidinone‐type antibacterials in which morpholine C‐ring of linezolid has been modified by substituted 3‐azabicyclo[3.3.0]octanyl rings. Acetamide or 1,2,3‐triazole heterocycle was used as C‐5 side chain of oxazolidinone. The resulting series of compounds was then screened in vitro against panel of susceptible and resistant Gram‐positive, Gram‐negative bacteria, and Mycobacterium tuberculosis (Mtb). Several analogs in this series exhibited potent in vitro antibacterial activity comparable or superior to linezolid against the tested bacteria. Compounds 10a, 10b, 11a, and 15a displayed highly potent activity against M. tuberculosis. Selected compound 10b showed good human microsomal stability and CYP‐profile, and showed low activity against hERG channel.

  DOI：

  10.1111/j.1747-0285.2012.01404.x