N-{N-[(2S)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-prolyl-L-phenylalanine benzyl ester | 357429-23-3

• 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: N-{N-[(2S)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-prolyl-L-phenylalanine benzyl ester
• CAS: 357429-23-3
• 化学式: C₃₈H₄₀N₆O₆
• 分子量: 676.772
• InChiKey: SLHVAEGSRAVRAQ-YRCZKMHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  50.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  151.73
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-{N-[(2S)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-prolyl-L-phenylalanine benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以96%的产率得到N-{N-[(2S)-4-oxoazetidine-2-carbonyl]-L-histidyl}-L-prolyl-L-phenylalanine
  参考文献：
  名称：

  β-Lactam Derivatives as Enzyme Inhibitors: Carboxy Peptidyl Derivatives of (S)-4-Oxoazetidine-2-carboxylate as Peptidomimetics

  摘要：

  4-Oxoazetidine-2-carboxylic acid, protected at the nitrogen by silyl groups, was coupled with amino acid and oligopeptide esters. Desilylation and deprotection of the amino acid residues yielded the free beta -lactam peptides. Structure and properties were elucidated by spectroscopic methods and discussed. Some selected compounds were tested as fibrinogen inhibitors and for thrombocyte aggregation. None of the compounds showed any activity up to a concentration of 10(-5) Mol/l. Some other compounds exhibited a weak inhibitory activity against elastase (PPE).

  DOI：

  10.1002/1521-4184(200105)334:5<167::aid-ardp167>3.3.co;2-f
• 作为产物：
  描述：

  N-Boc-L-prolyl-L-phenylalanine benzyl ester 在 盐酸 、 四丁基氟化铵 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.5h， 生成 N-{N-[(2S)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-prolyl-L-phenylalanine benzyl ester
  参考文献：
  名称：

  β-Lactam Derivatives as Enzyme Inhibitors: Carboxy Peptidyl Derivatives of (S)-4-Oxoazetidine-2-carboxylate as Peptidomimetics

  摘要：

  4-Oxoazetidine-2-carboxylic acid, protected at the nitrogen by silyl groups, was coupled with amino acid and oligopeptide esters. Desilylation and deprotection of the amino acid residues yielded the free beta -lactam peptides. Structure and properties were elucidated by spectroscopic methods and discussed. Some selected compounds were tested as fibrinogen inhibitors and for thrombocyte aggregation. None of the compounds showed any activity up to a concentration of 10(-5) Mol/l. Some other compounds exhibited a weak inhibitory activity against elastase (PPE).

  DOI：

  10.1002/1521-4184(200105)334:5<167::aid-ardp167>3.3.co;2-f