(S)-2-[(2S,3S)-2,3-Dihydroxy-3-((S)-1-isobutoxycarbonyl-2-phenyl-ethylcarbamoyl)-propionylamino]-3-phenyl-propionic acid isobutyl ester

• 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)-2-[(2S,3S)-2,3-Dihydroxy-3-((S)-1-isobutoxycarbonyl-2-phenyl-ethylcarbamoyl)-propionylamino]-3-phenyl-propionic acid isobutyl ester
• 英文别名: isobutyl (2S)-2-[[(2S,3S)-4-[[(1S)-1-benzyl-2-isobutoxy-2-oxo-ethyl]amino]-2,3-dihydroxy-4-oxo-butanoyl]amino]-3-phenyl-propanoate；2-methylpropyl (2S)-2-[[(2S,3S)-2,3-dihydroxy-4-[[(2S)-1-(2-methylpropoxy)-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoyl]amino]-3-phenylpropanoate
• 化学式: C₃₀H₄₀N₂O₈
• 分子量: 556.656
• InChiKey: UAMUURIJBKVASR-CQJMVLFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  L-phenylalanine isobutyl ester p-toluenesulfonate 、 D-酒石酸 在 N-甲基吗啉 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以55%的产率得到(S)-2-[(2S,3S)-2,3-Dihydroxy-3-((S)-1-isobutoxycarbonyl-2-phenyl-ethylcarbamoyl)-propionylamino]-3-phenyl-propionic acid isobutyl ester
  参考文献：
  名称：

  Synthesis of symmetrical pseudopeptides as potential inhibitors of the human immunodeficiency virus-1 protease

  摘要：

  It is demonstrated that HIV-1 protease is essential for the assembly and infectivity of the acquired immunodeficiency syndrome (AIDS) virus. This protease is an aspartyl protease with a 2-fold symmetry axis. Potential inhibitors were synthesized and consisted of a spacer linking 2 peptidic chains. They had to satisfy the following constraints: a C-2 symmetry axis, a backbone similar to the peptidic substrates, and side-chains filling the subsites S-n...S'(n). The compounds were synthesized via peptidic synthetic methods and evaluated in an enzymatic test with HIV-1 protease. Several compounds displayed an inhibitory activity at 10 mu M. They possessed the spacers CO, CO-CO, CO-CH2-CHOH-CO and the terminal chain Phe-O-iC(4)H(9). However, the structural-variation-based optimization of these different compounds failed and no potent inhibitors were prepared.

  DOI：

  10.1016/0223-5234(94)90025-6