(S)-N-(4-phenylbenzoyl)-(3-bromophenyl)alanylglycine nitrile

• 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: (S)-N-(4-phenylbenzoyl)-(3-bromophenyl)alanylglycine nitrile
• 英文别名: N-[(2S)-3-(3-bromophenyl)-1-(cyanomethylamino)-1-oxopropan-2-yl]-4-phenylbenzamide
• 化学式: C₂₄H₂₀BrN₃O₂
• 分子量: 462.346
• InChiKey: LJZGCVPFHDAQAO-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  82
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N-(4-phenylbenzoyl)-(3-bromophenyl)alanylglycine nitrile 、 苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 1.0h， 以59%的产率得到(S)-N-(4-phenylbenzoyl)-(3-biphenyl)alanylglycine nitrile
  参考文献：
  名称：

  Cathepsin B Inhibitors: Combining Dipeptide Nitriles with an Occluding Loop Recognition Element by Click Chemistry

  摘要：

  An active site mapping of human cathepsin B with dipeptide nitrile inhibitors was performed for a combinatorial approach by introducing several points of diversity and stepwise optimizing the inhibitor structure. To address the occluding loop of cathepsin B by a carboxylate moiety, click chemistry to generate linker-connected molecules was applied. Inhibitor 17 exhibited K-i values of 41.3 nM, 27.3 nM, or 19.2 nM, depending on the substrate and pH of the assay. Kinetic data were discussed with respect to the conformational selection and induced fit models.

  DOI：

  10.1021/acsmedchemlett.5b00474
• 作为产物：
  描述：

  Boc-L-3-溴苯丙氨酸 在 N-甲基吗啉 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 (S)-N-(4-phenylbenzoyl)-(3-bromophenyl)alanylglycine nitrile
  参考文献：
  名称：

  Cathepsin B Inhibitors: Combining Dipeptide Nitriles with an Occluding Loop Recognition Element by Click Chemistry

  摘要：

  An active site mapping of human cathepsin B with dipeptide nitrile inhibitors was performed for a combinatorial approach by introducing several points of diversity and stepwise optimizing the inhibitor structure. To address the occluding loop of cathepsin B by a carboxylate moiety, click chemistry to generate linker-connected molecules was applied. Inhibitor 17 exhibited K-i values of 41.3 nM, 27.3 nM, or 19.2 nM, depending on the substrate and pH of the assay. Kinetic data were discussed with respect to the conformational selection and induced fit models.

  DOI：

  10.1021/acsmedchemlett.5b00474