tert-butyl (S)-3-((S)-2-(benzyloxycarbonylamino)propanamido)-4-hydroxybutanoate | 1215015-80-7

• 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: tert-butyl (S)-3-((S)-2-(benzyloxycarbonylamino)propanamido)-4-hydroxybutanoate
• 英文别名: Z-Ala-Asp(OtBu)-ol；tert-butyl (3S)-4-hydroxy-3-[[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]amino]butanoate
• CAS: 1215015-80-7
• 化学式: C₁₉H₂₈N₂O₆
• 分子量: 380.441
• InChiKey: MSKJAIOQRDUFKX-ZFWWWQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-3-((S)-2-(benzyloxycarbonylamino)propanamido)-4-hydroxybutanoate 在 1% Pd/C 、 氢气 、 三氟乙酸 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Noncovalent Tripeptidyl Benzyl- and Cyclohexyl-Amine Inhibitors of the Cysteine Protease Caspase-1

  摘要：

  Potent and noncovalent inhibitors of caspase-1 were produced by incorporating a secondary amine (reduced amide) isostere in place of the conventional electrophile (e.g., aldehyde) that normally confers high potency to cysteine protease inhibitors. Benzyl- or cyclohexylamines produced potent, reversible, and competitive inhibitors that were selective for caspase-1 (e.g., K-i = 47 nM) over caspases 3 and 8 with minimal cytotoxicity. Unlike most cysteine protease inhibitors, these compounds do not react covalently and indiscriminately with thiols.

  DOI：

  10.1021/jm901790w
• 作为产物：
  描述：

  苄氧羰基-L-丙氨酸 、 (S)-tert-butyl 3-amino-4-hydroxybutanoate 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以1 g的产率得到tert-butyl (S)-3-((S)-2-(benzyloxycarbonylamino)propanamido)-4-hydroxybutanoate
  参考文献：
  名称：

  Noncovalent Tripeptidyl Benzyl- and Cyclohexyl-Amine Inhibitors of the Cysteine Protease Caspase-1

  摘要：

  Potent and noncovalent inhibitors of caspase-1 were produced by incorporating a secondary amine (reduced amide) isostere in place of the conventional electrophile (e.g., aldehyde) that normally confers high potency to cysteine protease inhibitors. Benzyl- or cyclohexylamines produced potent, reversible, and competitive inhibitors that were selective for caspase-1 (e.g., K-i = 47 nM) over caspases 3 and 8 with minimal cytotoxicity. Unlike most cysteine protease inhibitors, these compounds do not react covalently and indiscriminately with thiols.

  DOI：

  10.1021/jm901790w