4-hydroxy-3-(S)-(2-(S)-{3-methyl-2-(S)-[(naphthalene-2-carbonyl)amino]butyrylamino}propionylamino)butyric acid tert-butyl ester | 1215015-82-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: 4-hydroxy-3-(S)-(2-(S)-{3-methyl-2-(S)-[(naphthalene-2-carbonyl)amino]butyrylamino}propionylamino)butyric acid tert-butyl ester
• 英文别名: naphth-2-oyl-Val-Ala-Asp(OtBu)(OtBu)-ol；tert-butyl (3S)-4-hydroxy-3-[[(2S)-2-[[(2S)-3-methyl-2-(naphthalene-2-carbonylamino)butanoyl]amino]propanoyl]amino]butanoate
• CAS: 1215015-82-9
• 化学式: C₂₇H₃₇N₃O₆
• 分子量: 499.607
• InChiKey: LUNVFQNUDGJCNT-HYVJGQCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-(S)-(2-(S)-{3-methyl-2-(S)-[(naphthalene-2-carbonyl)amino]butyrylamino}propionylamino)butyric acid tert-butyl ester 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以82%的产率得到3-(S)-(2-(S)-{3-methyl-2-(S)-[(naphthalene-2-carbonyl)amino]butyrylamino}propionylamino)-4-oxobutyric acid tert-butyl ester
  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：

  、 2-萘甲酸 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0.4 g的产率得到4-hydroxy-3-(S)-(2-(S)-{3-methyl-2-(S)-[(naphthalene-2-carbonyl)amino]butyrylamino}propionylamino)butyric acid tert-butyl ester
  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