benzyl N-[(2S)-3-cyclohexyl-1-[methyl(methylamino)amino]-1-oxopropan-2-yl]carbamate | 1259946-44-5

• 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: benzyl N-[(2S)-3-cyclohexyl-1-[methyl(methylamino)amino]-1-oxopropan-2-yl]carbamate
• CAS: 1259946-44-5
• 化学式: C₁₉H₂₉N₃O₃
• 分子量: 347.458
• InChiKey: REAXJDWEMCLLFV-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  溴化氰 、 benzyl N-[(2S)-3-cyclohexyl-1-[methyl(methylamino)amino]-1-oxopropan-2-yl]carbamate 在 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以31%的产率得到N-(benzyloxycarbonyl)-cyclohexylalanyl-methylazalanine-nitrile
  参考文献：
  名称：

  Structural Optimization of Azadipeptide Nitriles Strongly Increases Association Rates and Allows the Development of Selective Cathepsin Inhibitors

  摘要：

  Using the example of cathepsin K, we demonstrate the design of highly potent and selective azadipeptide nitrite inhibitors A systematic scan with respect to P2 and P3 substituents was carried out Structural modifications strongly affected the enzyme-inhibitor association (but not dissociation) rate A combination of optimized P2 and P3 substituents with a methylation of the P3-P2 amide linker resulted in the picomolar cathepsin K inhibitor 19 with remarkable selectivity over cathepsins L, B, and S

  DOI：

  10.1021/jm101272p
• 作为产物：
  描述：

  CBZ-L-环己基丙氨酸 在 N-甲基吗啉 、 sodium hydroxide 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 benzyl N-[(2S)-3-cyclohexyl-1-[methyl(methylamino)amino]-1-oxopropan-2-yl]carbamate
  参考文献：
  名称：

  Structural Optimization of Azadipeptide Nitriles Strongly Increases Association Rates and Allows the Development of Selective Cathepsin Inhibitors

  摘要：

  Using the example of cathepsin K, we demonstrate the design of highly potent and selective azadipeptide nitrite inhibitors A systematic scan with respect to P2 and P3 substituents was carried out Structural modifications strongly affected the enzyme-inhibitor association (but not dissociation) rate A combination of optimized P2 and P3 substituents with a methylation of the P3-P2 amide linker resulted in the picomolar cathepsin K inhibitor 19 with remarkable selectivity over cathepsins L, B, and S

  DOI：

  10.1021/jm101272p

文献信息

• Structural Optimization of Azadipeptide Nitriles Strongly Increases Association Rates and Allows the Development of Selective Cathepsin Inhibitors
  作者：Maxim Frizler、Friederike Lohr、Norbert Furtmann、Julia Kläs、Michael Gütschow

  DOI：10.1021/jm101272p

  日期：2011.1.13

  Using the example of cathepsin K, we demonstrate the design of highly potent and selective azadipeptide nitrite inhibitors A systematic scan with respect to P2 and P3 substituents was carried out Structural modifications strongly affected the enzyme-inhibitor association (but not dissociation) rate A combination of optimized P2 and P3 substituents with a methylation of the P3-P2 amide linker resulted in the picomolar cathepsin K inhibitor 19 with remarkable selectivity over cathepsins L, B, and S