ethyl 2-((S)-1-((S)-6-(((benzyloxy)carbonyl)amino)-2-((S)-1-(2-(2-((S)-1-((tert-butoxycarbonyl)-D-phenylalanyl)pyrrolidin-2-yl)thiazol-4-yl)oxazole-4-carbonyl)pyrrolidine-2-carboxamido)hexanamido)ethyl)thiazole-4-carboxylate | 1453168-06-3

• 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: ethyl 2-((S)-1-((S)-6-(((benzyloxy)carbonyl)amino)-2-((S)-1-(2-(2-((S)-1-((tert-butoxycarbonyl)-D-phenylalanyl)pyrrolidin-2-yl)thiazol-4-yl)oxazole-4-carbonyl)pyrrolidine-2-carboxamido)hexanamido)ethyl)thiazole-4-carboxylate
• CAS: 1453168-06-3
• 化学式: C₅₂H₆₃N₉O₁₁S₂
• 分子量: 1054.26
• InChiKey: ZZRGPOQFZSFROS-UMBQMAJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.29
• 重原子数：
  74.0
• 可旋转键数：
  21.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  253.59
• 氢给体数：
  4.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-((S)-1-((S)-6-(((benzyloxy)carbonyl)amino)-2-((S)-1-(2-(2-((S)-1-((tert-butoxycarbonyl)-D-phenylalanyl)pyrrolidin-2-yl)thiazol-4-yl)oxazole-4-carbonyl)pyrrolidine-2-carboxamido)hexanamido)ethyl)thiazole-4-carboxylate 在 双氧水 、 苯甲醚 、 三氟乙酸 、 lithium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 2-((S)-1-((S)-2-((S)-1-(2-(2-((S)-1-(D-phenylalanyl)pyrrolidin-2-yl)thiazol-4-yl)oxazole-4-carbonyl)pyrrolidine-2-carboxamido)-6-(((benzyloxy)carbonyl)amino)hexanamido)ethyl)thiazole-4-carboxylic acid
  参考文献：
  名称：

  Mechanistic Studies of Sanguinamide B Derivatives: A Unique Inhibitor of Eukaryotic Ribosomes

  摘要：

  Described are mechanistic studies of two Sanguinamide B (San B) derivatives. These compounds were identified as eukaryotic ribosomal inhibitors. Two biotinylated San B derivatives were synthesized and used to capture protein targets in a pull-down assay. LC/MS/MS analysis of the San B-captured targets identified several proteins that comprise eukaryotic ribosomal subunits. The translation inhibitory effect of San B was confirmed using an in vitro translation assay. Moreover, an evaluation of cell death mechanisms is reported.

  DOI：

  10.1021/ol401749p
• 作为产物：
  描述：

  乙基2-[(1S)-1-氨基乙基]-1,3-噻唑-4-羧酸酯 在 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 苯甲醚 、 1-丙基磷酸酐 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 ethyl 2-((S)-1-((S)-6-(((benzyloxy)carbonyl)amino)-2-((S)-1-(2-(2-((S)-1-((tert-butoxycarbonyl)-D-phenylalanyl)pyrrolidin-2-yl)thiazol-4-yl)oxazole-4-carbonyl)pyrrolidine-2-carboxamido)hexanamido)ethyl)thiazole-4-carboxylate
  参考文献：
  名称：

  Mechanistic Studies of Sanguinamide B Derivatives: A Unique Inhibitor of Eukaryotic Ribosomes

  摘要：

  Described are mechanistic studies of two Sanguinamide B (San B) derivatives. These compounds were identified as eukaryotic ribosomal inhibitors. Two biotinylated San B derivatives were synthesized and used to capture protein targets in a pull-down assay. LC/MS/MS analysis of the San B-captured targets identified several proteins that comprise eukaryotic ribosomal subunits. The translation inhibitory effect of San B was confirmed using an in vitro translation assay. Moreover, an evaluation of cell death mechanisms is reported.

  DOI：

  10.1021/ol401749p