(S)-4-Benzyl-3-(2-{(R)-1-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-2-oxo-pyrrolidin-3-yl}-propionyl)-oxazolidin-2-one | 648414-76-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (S)-4-Benzyl-3-(2-{(R)-1-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-2-oxo-pyrrolidin-3-yl}-propionyl)-oxazolidin-2-one
• CAS: 648414-76-0
• 化学式: C₃₄H₃₃N₃O₅
• 分子量: 563.653
• InChiKey: JNSCYNDXZFVYBZ-CBHNQEKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  89.04
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-4-Benzyl-3-(2-{(R)-1-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-2-oxo-pyrrolidin-3-yl}-propionyl)-oxazolidin-2-one 在 氢氧化钾 、 羟胺 作用下， 以 甲醇 为溶剂， 生成 (2S)-N-hydroxy-2-((3R)-1-{4-[(2-methyl-4-quinolinyl)methoxy]phenyl}-2-oxopyrrolidinyl)propanamide 、 (2R)-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：

  [(R)-1-(4-Benzyloxy-phenyl)-2-oxo-pyrrolidin-3-yl]-acetic acid tert-butyl ester 在 palladium dihydroxide 正丁基锂 、 氢气 、 三甲基乙酰氯 、 双(三甲基硅烷基)氨基钾 、 caesium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 (S)-4-Benzyl-3-(2-{(R)-1-[4-(2-methyl-quinolin-4-ylmethoxy)-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