tert-butyl (4S)-5-[[(2S)-1-[[(2S)-1-[(2S)-2-[[2-hydroxy-1-oxo-1-(prop-2-enylamino)hex-5-en-3-yl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-[[(2S)-4-[(2-methylpropan-2-yl)oxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoyl]amino]-5-oxopentanoate | 274918-49-9

• 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: tert-butyl (4S)-5-[[(2S)-1-[[(2S)-1-[(2S)-2-[[2-hydroxy-1-oxo-1-(prop-2-enylamino)hex-5-en-3-yl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-[[(2S)-4-[(2-methylpropan-2-yl)oxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoyl]amino]-5-oxopentanoate
• CAS: 274918-49-9
• 化学式: C₄₆H₇₇N₇O₁₃
• 分子量: 936.156
• InChiKey: ROWMRPMSBKLMCB-OPKWMYKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  66.0
• 可旋转键数：
  23.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  276.97
• 氢给体数：
  7.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S)-5-[[(2S)-1-[[(2S)-1-[(2S)-2-[[2-hydroxy-1-oxo-1-(prop-2-enylamino)hex-5-en-3-yl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-[[(2S)-4-[(2-methylpropan-2-yl)oxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoyl]amino]-5-oxopentanoate 以70%的产率得到tert-butyl (4S)-5-[[(2S)-1-[[(2S)-1-[(2S)-2-[[1,2-dioxo-1-(prop-2-enylamino)hex-5-en-3-yl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-[[(2S)-4-[(2-methylpropan-2-yl)oxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoyl]amino]-5-oxopentanoate
  参考文献：
  名称：

  α-Ketoamides, α-ketoesters and α-diketones as HCV NS3 protease inhibitors

  摘要：

  Peptide-based alpha-ketoamides, alpha-ketoesters and alpha-diketones were designed, synthesized and evaluated against HCV NS3 protease. alpha-Ketoamides have the highest affinity among the three classes, with 8 being the most potent inhibitor with an IC50 Of 340 nM. (C) 2000 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00074-3
• 作为产物：
  描述：

  2-甲基-2-丙基(1-氧代-4-戊烯-2-基)氨基甲酸酯 在 盐酸 、 TEA 、 sodium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl (4S)-5-[[(2S)-1-[[(2S)-1-[(2S)-2-[[2-hydroxy-1-oxo-1-(prop-2-enylamino)hex-5-en-3-yl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-[[(2S)-4-[(2-methylpropan-2-yl)oxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoyl]amino]-5-oxopentanoate
  参考文献：
  名称：

  α-Ketoamides, α-ketoesters and α-diketones as HCV NS3 protease inhibitors

  摘要：

  Peptide-based alpha-ketoamides, alpha-ketoesters and alpha-diketones were designed, synthesized and evaluated against HCV NS3 protease. alpha-Ketoamides have the highest affinity among the three classes, with 8 being the most potent inhibitor with an IC50 Of 340 nM. (C) 2000 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00074-3