methyl (2S)-2-[[[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutyl]-methylcarbamoyl]amino]-4-methylpentanoate | 733744-92-8

• 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: methyl (2S)-2-[[[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutyl]-methylcarbamoyl]amino]-4-methylpentanoate
• CAS: 733744-92-8
• 化学式: C₂₄H₃₉N₃O₆
• 分子量: 465.59
• InChiKey: JQIOTUMFIRNALU-SLFFLAALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  33.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  117.2
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutyl]-methylcarbamoyl]amino]-4-methylpentanoate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (2S)-2-[[[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutyl]-methylcarbamoyl]amino]-4-methylpentanoic acid
  参考文献：
  名称：

  Probing pockets S2–S4′ of the γ-secretase active site with (hydroxyethyl)urea peptidomimetics

  摘要：

  (Hydroxyethyl)urea peptidomimetics are potent inhibitors of gamma-secretase that are accessible in a few synthetic steps. Systematic alteration of P2-P4' revealed that the corresponding S2-S4' active site pockets accommodate a variety of substituents, consistent with the fact that this protease cleaves a variety of single-pass membrane proteins; however, phenylalanine is not well tolerated at P2'. A compound spanning P2-P3' was identified as a low nM inhibitor of gamma-secretase activity both in cells and under cell-free conditions. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2004.01.077
• 作为产物：
  描述：

  1-苄基-2,3-环氧正丙基-氨基甲酸叔丁酯 以 异丙醇 为溶剂， 反应 16.0h， 生成 methyl (2S)-2-[[[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutyl]-methylcarbamoyl]amino]-4-methylpentanoate
  参考文献：
  名称：

  Probing pockets S2–S4′ of the γ-secretase active site with (hydroxyethyl)urea peptidomimetics

  摘要：

  (Hydroxyethyl)urea peptidomimetics are potent inhibitors of gamma-secretase that are accessible in a few synthetic steps. Systematic alteration of P2-P4' revealed that the corresponding S2-S4' active site pockets accommodate a variety of substituents, consistent with the fact that this protease cleaves a variety of single-pass membrane proteins; however, phenylalanine is not well tolerated at P2'. A compound spanning P2-P3' was identified as a low nM inhibitor of gamma-secretase activity both in cells and under cell-free conditions. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2004.01.077