(S)-tert-Butoxycarbonylamino-[(R)-1-(4-hydroxy-phenyl)-2-oxo-pyrrolidin-3-yl]-acetic acid methyl ester | 300856-36-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-tert-Butoxycarbonylamino-[(R)-1-(4-hydroxy-phenyl)-2-oxo-pyrrolidin-3-yl]-acetic acid methyl ester
• CAS: 300856-36-4
• 化学式: C₁₈H₂₄N₂O₆
• 分子量: 364.398
• InChiKey: HCFKCWCTYMVWSS-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105.17
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-tert-Butoxycarbonylamino-[(R)-1-(4-hydroxy-phenyl)-2-oxo-pyrrolidin-3-yl]-acetic acid methyl ester 在 氢氧化钾 、 羟胺 、 caesium carbonate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 (αS,3R)-α-amino-N-hydroxy-1-[4-[(2-methyl-4-quinolinyl)methoxy]phenyl]-2-oxo-3-pyrrolidineacetamide
  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：

  在 palladium dihydroxide 氢气 、 三乙酰氧基硼氢化钠 作用下， 以 甲醇 、 1,2-二氯乙烷 、 甲苯 为溶剂， 生成 (S)-tert-Butoxycarbonylamino-[(R)-1-(4-hydroxy-phenyl)-2-oxo-pyrrolidin-3-yl]-acetic acid methyl ester
  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