(S)-4-{(S)-2-[(S)-2-((S)-2-Acetylamino-3-carboxy-propionylamino)-4-carboxy-butyrylamino]-3,3-diphenyl-propionylamino}-4-[(S)-2-cyclohexyl-1-((R)-2-mercapto-1-phenethylcarbamoyl-ethylcarbamoyl)-ethylcarbamoyl]-butyric acid

• 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)-4-{(S)-2-[(S)-2-((S)-2-Acetylamino-3-carboxy-propionylamino)-4-carboxy-butyrylamino]-3,3-diphenyl-propionylamino}-4-[(S)-2-cyclohexyl-1-((R)-2-mercapto-1-phenethylcarbamoyl-ethylcarbamoyl)-ethylcarbamoyl]-butyric acid
• 英文别名: 4-(2-Acetylamino-3-carboxy-propionylamino)-4-(1-{1-[2-cyclohexyl-1-(2-mercapto-1-phenethylcarbamoyl-ethylcarbamoyl)-ethylcarbamoyl]-3-methoxycarbonyl-propylcarbamoyl}-2,2-diphenyl-ethylcarbamoyl)-butyric acid；(4S)-4-[[(2S)-2-acetamido-3-carboxypropanoyl]amino]-5-[[(2S)-1-[[(2S)-4-carboxy-1-[[(2S)-3-cyclohexyl-1-oxo-1-[[(2R)-1-oxo-1-(2-phenylethylamino)-3-sulfanylpropan-2-yl]amino]propan-2-yl]amino]-1-oxobutan-2-yl]amino]-1-oxo-3,3-diphenylpropan-2-yl]amino]-5-oxopentanoic acid
• 化学式: C₅₁H₆₅N₇O₁₃S
• 分子量: 1016.18
• InChiKey: MAYPPTYEEGIGNJ-VUKWIJDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  72
• 可旋转键数：
  29
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  317
• 氢给体数：
  11
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  N¹-(2-phenylethyl)-S-trityl-L-cysteinamide 、 Ac-Asp(OtBu)-Glu(OtBu)-Dif-Glu(OtBu)-ChaOH 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以37%的产率得到(S)-4-{(S)-2-[(S)-2-((S)-2-Acetylamino-3-carboxy-propionylamino)-4-carboxy-butyrylamino]-3,3-diphenyl-propionylamino}-4-[(S)-2-cyclohexyl-1-((R)-2-mercapto-1-phenethylcarbamoyl-ethylcarbamoyl)-ethylcarbamoyl]-butyric acid
  参考文献：
  名称：

  Phenethyl Amides as Novel Noncovalent Inhibitors of Hepatitis C Virus NS3/4A Protease:  Discovery, Initial SAR, and Molecular Modeling

  摘要：

  The discovery of novel, reversible and competitive tripeptide inhibitors of the Hepatitis C virus NS3/4A serine protease is described. These inhibitors are characterized by the presence of a C-terminal phenethyl amide group, which extends into the prime side of the enzyme. Initial SAR together with molecular modeling and data from site-directed mutagenesis suggest an interaction of the phenethyl amide group with Lys-136.

  DOI：

  10.1021/jm025594q