N-((S)-3-{3-Fluoro-4-[4-(5-hydroxymethyl-furan-2-ylmethyl)-piperazin-1-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide | 548762-76-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: N-((S)-3-{3-Fluoro-4-[4-(5-hydroxymethyl-furan-2-ylmethyl)-piperazin-1-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide
• 英文别名: N-[[(5S)-3-[3-fluoro-4-[4-[[5-(hydroxymethyl)furan-2-yl]methyl]piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
• CAS: 548762-76-1
• 化学式: C₂₂H₂₇FN₄O₅
• 分子量: 446.479
• InChiKey: KKCVFRZVIBHRCH-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  98.5
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-((S)-3-{3-Fluoro-4-[4-(5-hydroxymethyl-furan-2-ylmethyl)-piperazin-1-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide 、 乙酸酐 在 TEA 作用下， 反应 24.0h， 生成 Acetic acid 5-(4-{4-[(S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-piperazin-1-ylmethyl)-furan-2-ylmethyl ester
  参考文献：
  名称：

  Synthesis and SAR of novel oxazolidinones: Discovery of ranbezolid

  摘要：

  Novel oxazolidinones were synthesized containing a number of substituted five-membered heterocycles attached to the 'piperazinyl-phenyl-oxazolidinone' core of eperezolid. Further, the piperazine ring of the core was replaced by other diamino-heterocycles. These modifications led to several compounds with potent activity against a spectrum of resistant and susceptible Gram-positive organisms, along with the identification of ranbezolid (RBx 7644) as a clinical candidate. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.063
• 作为产物：
  描述：

  4-(4-Boc-哌嗪-1-基)-3-氟苯胺 在 palladium on activated charcoal sodium tetrahydroborate 、 正丁基锂 、 sodium azide 、 TEA 、 氢气 、 碳酸氢钠 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -78.0~80.0 ℃ 、379.21 kPa 条件下， 反应 8.5h， 生成 N-((S)-3-{3-Fluoro-4-[4-(5-hydroxymethyl-furan-2-ylmethyl)-piperazin-1-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide
  参考文献：
  名称：

  Synthesis and SAR of novel oxazolidinones: Discovery of ranbezolid

  摘要：

  Novel oxazolidinones were synthesized containing a number of substituted five-membered heterocycles attached to the 'piperazinyl-phenyl-oxazolidinone' core of eperezolid. Further, the piperazine ring of the core was replaced by other diamino-heterocycles. These modifications led to several compounds with potent activity against a spectrum of resistant and susceptible Gram-positive organisms, along with the identification of ranbezolid (RBx 7644) as a clinical candidate. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.063

文献信息

• Synthesis and SAR of novel oxazolidinones: Discovery of ranbezolid
  作者：Biswajit Das、Sonali Rudra、Ajay Yadav、Abhijit Ray、A.V.S. Raja Rao、A.S.S.V. Srinivas、Ajay Soni、Suman Saini、Shalini Shukla、Manisha Pandya、Pragya Bhateja、Sunita Malhotra、Tarun Mathur、S.K. Arora、Ashok Rattan、Anita Mehta

  DOI：10.1016/j.bmcl.2005.06.063

  日期：2005.10

  Novel oxazolidinones were synthesized containing a number of substituted five-membered heterocycles attached to the 'piperazinyl-phenyl-oxazolidinone' core of eperezolid. Further, the piperazine ring of the core was replaced by other diamino-heterocycles. These modifications led to several compounds with potent activity against a spectrum of resistant and susceptible Gram-positive organisms, along with the identification of ranbezolid (RBx 7644) as a clinical candidate. (c) 2005 Elsevier Ltd. All rights reserved.