[(4S,5R)-2-oxo-4-[(4-phenylpiperazin-1-yl)methyl]-1,3-oxazolidin-5-yl]methyl 2-phenylacetate | 1333501-81-7

• 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: [(4S,5R)-2-oxo-4-[(4-phenylpiperazin-1-yl)methyl]-1,3-oxazolidin-5-yl]methyl 2-phenylacetate
• CAS: 1333501-81-7
• 化学式: C₂₃H₂₇N₃O₄
• 分子量: 409.485
• InChiKey: PEYFDUDIYDGOOB-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  71.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (R)-1-(triphenylmethoxy)-2-[(azidocarbonyl)oxy]-3-butene 在 盐酸 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 21.17h， 生成 [(4S,5R)-2-oxo-4-[(4-phenylpiperazin-1-yl)methyl]-1,3-oxazolidin-5-yl]methyl 2-phenylacetate
  参考文献：
  名称：

  Synthesis and Stereospecificity of 4,5-Disubstituted Oxazolidinone Ligands Binding to T-box Riboswitch RNA

  摘要：

  The enantiomers and the cis isomers of two previously studied 4,5-disubstituted oxazolidinones have been synthesized, and their binding to the T-box riboswitch antiterminator model RNA has been investigated in detail. Characterization of ligand affinities and binding site localization indicates that there is little stereospecific discrimination for binding antiterminator RNA alone. This binding similarity between enantiomers is likely due to surface binding, which accommodates ligand conformations 1 that result in comparable ligand-antiterminator contacts. These results have significant implications for T-box antiterminator-targeted drug discovery and, in general, for targeting other medicinally relevant RNA that do not present deep binding pockets.

  DOI：

  10.1021/jm2006904

文献信息

• Synthesis and Stereospecificity of 4,5-Disubstituted Oxazolidinone Ligands Binding to T-box Riboswitch RNA
  作者：Crina M. Orac、Shu Zhou、John A. Means、David Boehm、Stephen C. Bergmeier、Jennifer V. Hines

  DOI：10.1021/jm2006904

  日期：2011.10.13

  The enantiomers and the cis isomers of two previously studied 4,5-disubstituted oxazolidinones have been synthesized, and their binding to the T-box riboswitch antiterminator model RNA has been investigated in detail. Characterization of ligand affinities and binding site localization indicates that there is little stereospecific discrimination for binding antiterminator RNA alone. This binding similarity between enantiomers is likely due to surface binding, which accommodates ligand conformations 1 that result in comparable ligand-antiterminator contacts. These results have significant implications for T-box antiterminator-targeted drug discovery and, in general, for targeting other medicinally relevant RNA that do not present deep binding pockets.