(2-Benzenesulfonyl-3,3-diethyl-4-oxo-azetidin-1-yl)-hydroxy-acetic acid ethyl ester | 863480-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (2-Benzenesulfonyl-3,3-diethyl-4-oxo-azetidin-1-yl)-hydroxy-acetic acid ethyl ester
• 英文别名: Ethyl 2-[2-(benzenesulfonyl)-3,3-diethyl-4-oxoazetidin-1-yl]-2-hydroxyacetate
• CAS: 863480-44-8
• 化学式: C₁₇H₂₃NO₆S
• 分子量: 369.439
• InChiKey: IYFIAZMZMRMTGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2-Benzenesulfonyl-3,3-diethyl-4-oxo-azetidin-1-yl)-hydroxy-acetic acid ethyl ester 、 2-(甲氧基羰基)苯基异氰酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-[(2-Benzenesulfonyl-3,3-diethyl-4-oxo-azetidin-1-yl)-ethoxycarbonyl-methoxycarbonylamino]-benzoic acid methyl ester
  参考文献：
  名称：

  Design, Synthesis, and Enzymatic Evaluation of N-Acyloxyalkyl- and N¹-Oxazolidin-2,4-dion-5-yl-Substituted β-lactams as Novel Inhibitors of Human Leukocyte Elastase

  摘要：

  Human leukocyte elastase (HLE) is a serine protease that very efficiently degrades various tissue matrix proteins such as elastin. The imbalance between HLE and its endogenous inhibitors leads to excessive elastin proteolysis and is considered to be responsible for the onset of chronic obstructive pulmonary disease (COPD). A novel series of C-3-, C-4-, and N-1-substituted azetidin-2-ones were prepared as potential mechanism-based inhibitors of HLE to restore the protease/antiprotease imbalance. N-Acyloxyalkylazetidin-2-ones, 4, and their carbamate counterparts, 5, are weak HLE inhibitors, being 5 times less active than their bicyclic oxazolidin-2,4-dione-substituted analogues, 6, containing an electron-withdrawing substituent at C-4. Compounds 6 containing a C-4 substituent exist as two diastereomeric pairs of enantiomers, each pair presenting similar inhibitory activity against HLE. Comparative docking experiments with the C-4-substituted oxazolidin-2,4-dione inhibitors 6 suggest that only the 4R,5 ' S and 4S,5'S diastereomers consistently interact with the beta-lactam carbonyl carbon atom accessible to the serine hydroxyl oxygen.

  DOI：

  10.1021/jm0501331
• 作为产物：
  描述：

  2-吖丁啶酮,4-(乙酰氧基)-3,3-二乙基- 在 sodium hydroxide 、 四丁基溴化铵 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.0h， 生成 (2-Benzenesulfonyl-3,3-diethyl-4-oxo-azetidin-1-yl)-hydroxy-acetic acid ethyl ester
  参考文献：
  名称：

  Design, Synthesis, and Enzymatic Evaluation of N-Acyloxyalkyl- and N¹-Oxazolidin-2,4-dion-5-yl-Substituted β-lactams as Novel Inhibitors of Human Leukocyte Elastase

  摘要：

  Human leukocyte elastase (HLE) is a serine protease that very efficiently degrades various tissue matrix proteins such as elastin. The imbalance between HLE and its endogenous inhibitors leads to excessive elastin proteolysis and is considered to be responsible for the onset of chronic obstructive pulmonary disease (COPD). A novel series of C-3-, C-4-, and N-1-substituted azetidin-2-ones were prepared as potential mechanism-based inhibitors of HLE to restore the protease/antiprotease imbalance. N-Acyloxyalkylazetidin-2-ones, 4, and their carbamate counterparts, 5, are weak HLE inhibitors, being 5 times less active than their bicyclic oxazolidin-2,4-dione-substituted analogues, 6, containing an electron-withdrawing substituent at C-4. Compounds 6 containing a C-4 substituent exist as two diastereomeric pairs of enantiomers, each pair presenting similar inhibitory activity against HLE. Comparative docking experiments with the C-4-substituted oxazolidin-2,4-dione inhibitors 6 suggest that only the 4R,5 ' S and 4S,5'S diastereomers consistently interact with the beta-lactam carbonyl carbon atom accessible to the serine hydroxyl oxygen.

  DOI：

  10.1021/jm0501331