4(S)-benzyl-3(R)-methylazetidin-2-one

• 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: 4(S)-benzyl-3(R)-methylazetidin-2-one
• 英文别名: (3R,4S)-4-benzyl-3-methylazetidin-2-one
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: LYHNJWQOISHIOL-SCZZXKLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  Z-Phe-O-COO-isoBu 在 palladium dihydroxide 2,6-二叔丁基苯酚 、 氢气 、 silver benzoate 、 碳酸氢钠 、 甲基磺酰氯 、 三乙胺 、 N,N-二异丙基乙胺 、 cesium fluoride 、 lithium diisopropyl amide 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 41.34h， 生成 4(S)-benzyl-3(R)-methylazetidin-2-one
  参考文献：
  名称：

  β-Lactam Derivatives as Inhibitors of Human Cytomegalovirus Protease

  摘要：

  The development of novel monobactam inhibitors of HCMV protease incorporating a carbon side chain at C-4 and a urea function at N-1 is described. Substitution with small groups at the C-3 position of the beta-lactam ring gave an increase in enzymatic activity and in stability; however, a lack of selectivity against other serine proteases was noted. The use of both tri- and tetrasubstituted urea functionalities gave effective inhibitors of HCMV protease. Benzyl substitution of the urea moiety was beneficial, especially when strong electron-withdrawing groups where attached at the para position. Modest antiviral activity was found in a plaque reduction assay.

  DOI：

  10.1021/jm980131z

文献信息

• β-Lactam Derivatives as Inhibitors of Human Cytomegalovirus Protease
  作者：Christiane Yoakim、William W. Ogilvie、Dale R. Cameron、Catherine Chabot、Ingrid Guse、Bruno Haché、Julie Naud、Jeff A. O'Meara、Raymond Plante、Robert Déziel

  DOI：10.1021/jm980131z

  日期：1998.7.1

  The development of novel monobactam inhibitors of HCMV protease incorporating a carbon side chain at C-4 and a urea function at N-1 is described. Substitution with small groups at the C-3 position of the beta-lactam ring gave an increase in enzymatic activity and in stability; however, a lack of selectivity against other serine proteases was noted. The use of both tri- and tetrasubstituted urea functionalities gave effective inhibitors of HCMV protease. Benzyl substitution of the urea moiety was beneficial, especially when strong electron-withdrawing groups where attached at the para position. Modest antiviral activity was found in a plaque reduction assay.