tert-butyl (4S)-5-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(3S)-1,2-dioxo-1-(prop-2-enylamino)pentan-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 | 274918-62-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: tert-butyl (4S)-5-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(3S)-1,2-dioxo-1-(prop-2-enylamino)pentan-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: 274918-62-6
• 化学式: C₄₅H₇₅N₇O₁₃
• 分子量: 922.13
• InChiKey: MEEZOILZCWPNGJ-VKGMDSSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  65
• 可旋转键数：
  28
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  274
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S)-5-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(3S)-1,2-dioxo-1-(prop-2-enylamino)pentan-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 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到(4S)-4-[[(2S)-2-amino-3-carboxypropanoyl]amino]-5-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(3S)-1,2-dioxo-1-(prop-2-enylamino)pentan-3-yl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-5-oxopentanoic acid
  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：

  (2R,3S)-3-Benzyloxycarbonylamino-2-hydroxy-pentanoic acid methyl ester 在 palladium on activated charcoal lithium hydroxide 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl (4S)-5-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(3S)-1,2-dioxo-1-(prop-2-enylamino)pentan-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