N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-proline benzyl ester | 357429-20-0

• 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)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-proline benzyl ester
• CAS: 357429-20-0
• 化学式: C₃₅H₄₅N₅O₅Si
• 分子量: 643.858
• InChiKey: YMLJXTBGCRPPBX-DTXPUJKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  46.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  113.84
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-proline benzyl ester 在 palladium on activated charcoal 四丁基氟化铵 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 0.5h， 生成 N-{N-[(2S)-4-oxoazetidine-2-carbonyl]-L-histidyl}-L-proline
  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：

  (4S)-N-(叔丁基二甲基硅)氮杂环丁烷-2-酮-4-羧酸 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-proline 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