(3S)-1-[(p-nitrobenzyloxy)2-acetyloxyacetyl]-3-(acetylamino)azetidin-2-one | 253445-85-1

• 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: (3S)-1-[(p-nitrobenzyloxy)2-acetyloxyacetyl]-3-(acetylamino)azetidin-2-one
• 英文别名: (4-nitrophenyl)methyl 2-[(3S)-3-acetamido-2-oxoazetidin-1-yl]-2-acetyloxyacetate
• CAS: 253445-85-1
• 化学式: C₁₆H₁₇N₃O₈
• 分子量: 379.326
• InChiKey: SFGGGBHSSBLPJZ-CFMCSPIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-乙基吗啉 、 (3S)-1-[(p-nitrobenzyloxy)2-acetyloxyacetyl]-3-(acetylamino)azetidin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 2.0h， 以95%的产率得到2-[(3S)-3-acetamido-2-oxoazetidin-1-yl]-2-acetyloxyacetate;4-ethylmorpholin-4-ium
  参考文献：
  名称：

  Synthesis, reactivity and biochemical evaluation of 1,3-substituted azetidin-2-ones as enzyme inhibitors

  摘要：

  A series of monocyclic azetidinones were prepared, bearing, at position C-3, an acetylamino or a bromo substituent, at position N-1, a carboxymethyl group protected as p-nitrobenzyl ester (PNB) and alpha-functionalized with a potential leaving group (LG). These structures were designed as potential suicide-inhibitors of enzymes containing a serine nucleophile in their active site. The beta-lactam ring of these molecules was found to be stable in phosphate buffer (pH 7.5), but the PNB ester was rapidly cleaved. This constitutes a practical method of in situ deprotection. Depending on the nature of the LG group on the carboxymethyl chain, substitution of this group (LG = F) or decarboxylation (LG = SO2Ph) was observed under hydrolytic conditions. The 1,3-disubstituted azetidinones were inactive against beta-lactamases of classes A, B, C, and D. Three compounds behaved as weak reversible inhibitors of porcine pancreatic elastase (PPE). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00819-4
• 作为产物：
  描述：

  p-nitrobenzyl glyoxylate monohydrate 在 potassium carbonate 作用下， 以 水 、 乙腈 、 苯 为溶剂， 反应 7.75h， 生成 (3S)-1-[(p-nitrobenzyloxy)2-acetyloxyacetyl]-3-(acetylamino)azetidin-2-one
  参考文献：
  名称：

  Synthesis, reactivity and biochemical evaluation of 1,3-substituted azetidin-2-ones as enzyme inhibitors

  摘要：

  A series of monocyclic azetidinones were prepared, bearing, at position C-3, an acetylamino or a bromo substituent, at position N-1, a carboxymethyl group protected as p-nitrobenzyl ester (PNB) and alpha-functionalized with a potential leaving group (LG). These structures were designed as potential suicide-inhibitors of enzymes containing a serine nucleophile in their active site. The beta-lactam ring of these molecules was found to be stable in phosphate buffer (pH 7.5), but the PNB ester was rapidly cleaved. This constitutes a practical method of in situ deprotection. Depending on the nature of the LG group on the carboxymethyl chain, substitution of this group (LG = F) or decarboxylation (LG = SO2Ph) was observed under hydrolytic conditions. The 1,3-disubstituted azetidinones were inactive against beta-lactamases of classes A, B, C, and D. Three compounds behaved as weak reversible inhibitors of porcine pancreatic elastase (PPE). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00819-4