tert-butyl (S,E)-3-(benzyloxycarbonylamino)-6-oxo-6-phenylhex-4-enoate | 1215015-96-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (S,E)-3-(benzyloxycarbonylamino)-6-oxo-6-phenylhex-4-enoate
• 英文别名: tert-butyl (E,3S)-6-oxo-6-phenyl-3-(phenylmethoxycarbonylamino)hex-4-enoate
• CAS: 1215015-96-5
• 化学式: C₂₄H₂₇NO₅
• 分子量: 409.482
• InChiKey: LUWKXDJCMPZBKK-DAMWEWLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (S,E)-3-(benzyloxycarbonylamino)-6-oxo-6-phenylhex-4-enoate 在 palladium 10% on activated carbon 、 氢气 、 三氟乙酸 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 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：

  (苯甲酰基甲基)三苯基溴化膦 、 (S)-4-oxo-3-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester 以 乙酸乙酯 为溶剂， 反应 2.0h， 以82%的产率得到tert-butyl (S,E)-3-(benzyloxycarbonylamino)-6-oxo-6-phenylhex-4-enoate
  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

文献信息

• Noncovalent Tripeptidyl Benzyl- and Cyclohexyl-Amine Inhibitors of the Cysteine Protease Caspase-1
  作者：Reik Löser、Giovanni Abbenante、Praveen K. Madala、Maria Halili、Giang T. Le、David P. Fairlie

  DOI：10.1021/jm901790w

  日期：2010.3.25

  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.