(2S,5S,6S)-3-aza-3-(benzyloxycarbonyl)-6-[[(tert-butyloxycarbonyl)-L-valinyl]amino]-5-hydroxy-2,7-diphenylheptanoyl amide | 500767-28-2

• 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: (2S,5S,6S)-3-aza-3-(benzyloxycarbonyl)-6-[[(tert-butyloxycarbonyl)-L-valinyl]amino]-5-hydroxy-2,7-diphenylheptanoyl amide
• 英文别名: benzyl N-[(1S)-2-amino-2-oxo-1-phenylethyl]-N-[(2S,3S)-2-hydroxy-3-[[(2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]-4-phenylbutyl]carbamate
• CAS: 500767-28-2
• 化学式: C₃₆H₄₆N₄O₇
• 分子量: 646.784
• InChiKey: VTWQLNNBUWHVBR-ORYMTKCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  47
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  160
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,5S,6S)-3-aza-3-(benzyloxycarbonyl)-6-[[(tert-butyloxycarbonyl)-L-valinyl]amino]-5-hydroxy-2,7-diphenylheptanoyl amide 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 生成 [(2S,3S)-3-((S)-2-Amino-3-methyl-butyrylamino)-2-hydroxy-4-phenyl-butyl]-((S)-carbamoyl-phenyl-methyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Design and Synthesis of Plasmepsin I and Plasmepsin II Inhibitors with Activity in Plasmodium falciparum-Infected Cultured Human Erythrocytes

  摘要：

  A series of protease inhibitors targeted at the malarial enzymes plasmepsin I and II, and encompassing a basic hydroxyethylamine transition state isostere scaffold, was prepared. The substituents in the P1' position were varied and the biological activities expressed in K-i-values ranged from 60 to > 2000 nM. A more than 4-fold selectivity for either of the plasmepsins could be achieved. All of the active compounds exhibited high preference for the plasmepsins over cathepsin D, the most closely related human protease. A few active compounds were shown to inhibit parasite growth in cultured infected human erythrocytes. An ED50 value as low as 1.6 muM was observed for one of the inhibitors despite K-i values of 115 nM (Plm I) and 121 nM (Plm II).

  DOI：

  10.1021/jm020951i
• 作为产物：
  描述：

  L-苯甘氨酰胺 在 盐酸 、 potassium carbonate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 生成 (2S,5S,6S)-3-aza-3-(benzyloxycarbonyl)-6-[[(tert-butyloxycarbonyl)-L-valinyl]amino]-5-hydroxy-2,7-diphenylheptanoyl amide
  参考文献：
  名称：

  Design and Synthesis of Plasmepsin I and Plasmepsin II Inhibitors with Activity in Plasmodium falciparum-Infected Cultured Human Erythrocytes

  摘要：

  A series of protease inhibitors targeted at the malarial enzymes plasmepsin I and II, and encompassing a basic hydroxyethylamine transition state isostere scaffold, was prepared. The substituents in the P1' position were varied and the biological activities expressed in K-i-values ranged from 60 to > 2000 nM. A more than 4-fold selectivity for either of the plasmepsins could be achieved. All of the active compounds exhibited high preference for the plasmepsins over cathepsin D, the most closely related human protease. A few active compounds were shown to inhibit parasite growth in cultured infected human erythrocytes. An ED50 value as low as 1.6 muM was observed for one of the inhibitors despite K-i values of 115 nM (Plm I) and 121 nM (Plm II).

  DOI：

  10.1021/jm020951i