(S)-4-Benzyl-3-{2-[(R)-1-(4-hydroxy-phenyl)-2-oxo-pyrrolidin-3-yl]-propionyl}-oxazolidin-2-one | 648414-75-9

• 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: (S)-4-Benzyl-3-{2-[(R)-1-(4-hydroxy-phenyl)-2-oxo-pyrrolidin-3-yl]-propionyl}-oxazolidin-2-one
• CAS: 648414-75-9
• 化学式: C₂₃H₂₄N₂O₅
• 分子量: 408.454
• InChiKey: UCVXPWAVYOUVCY-RUTXASTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  87.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-4-Benzyl-3-{2-[(R)-1-(4-hydroxy-phenyl)-2-oxo-pyrrolidin-3-yl]-propionyl}-oxazolidin-2-one 在 氢氧化钾 、 羟胺 、 caesium carbonate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 (2S)-N-hydroxy-2-((3R)-1-{4-[(2-methyl-4-quinolinyl)methoxy]phenyl}-2-oxopyrrolidinyl)propanamide
  参考文献：
  名称：

  Discovery of N-Hydroxy-2-(2-oxo-3-pyrrolidinyl)acetamides as potent and selective inhibitors of tumor necrosis factor-α converting enzyme (TACE)

  摘要：

  New inhibitors of tumor necrosis factor-a converting enzyme (TACE) were discovered using an N-hydroxy-2-(2-oxo-3-pyrrolidinyl)acetamide scaffold. The series was found to be potent in a porcine TACE (pTACE) assay with IC50S typically below 5 nM. For most compounds, selectivity for pTACE relative to MMP-1,-2, and -9 is at least 300-fold. Compound 2o was potent in inhibition of TNFalpha production in a human whole blood assay (WBA) with an IC50 of 0.42 muM. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00313-5
• 作为产物：
  描述：

  (S)-4-Benzyl-3-{2-[(R)-1-(4-benzyloxy-phenyl)-2-oxo-pyrrolidin-3-yl]-propionyl}-oxazolidin-2-one 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 以74%的产率得到(S)-4-Benzyl-3-{2-[(R)-1-(4-hydroxy-phenyl)-2-oxo-pyrrolidin-3-yl]-propionyl}-oxazolidin-2-one
  参考文献：
  名称：

  Discovery of N-Hydroxy-2-(2-oxo-3-pyrrolidinyl)acetamides as potent and selective inhibitors of tumor necrosis factor-α converting enzyme (TACE)

  摘要：

  New inhibitors of tumor necrosis factor-a converting enzyme (TACE) were discovered using an N-hydroxy-2-(2-oxo-3-pyrrolidinyl)acetamide scaffold. The series was found to be potent in a porcine TACE (pTACE) assay with IC50S typically below 5 nM. For most compounds, selectivity for pTACE relative to MMP-1,-2, and -9 is at least 300-fold. Compound 2o was potent in inhibition of TNFalpha production in a human whole blood assay (WBA) with an IC50 of 0.42 muM. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00313-5