5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[2-[2-[2-[2-[3-[4-[(6S,12R,19S,22S,25S)-12-benzyl-19-methyl-11,14,21,24,30-pentaoxo-33-oxa-4,17-dithia-10,13,20,23,29,34,35,36-octazahexacyclo[29.2.1.12,5.115,18.06,10.025,29]hexatriaconta-1(34),2,5(36),15,18(35),31-hexaen-22-yl]butylamino]-3-oxopropoxy]ethoxy]ethoxy]ethoxy]ethyl]pentanamide | 1453168-14-3

• 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: 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[2-[2-[2-[2-[3-[4-[(6S,12R,19S,22S,25S)-12-benzyl-19-methyl-11,14,21,24,30-pentaoxo-33-oxa-4,17-dithia-10,13,20,23,29,34,35,36-octazahexacyclo[29.2.1.12,5.115,18.06,10.025,29]hexatriaconta-1(34),2,5(36),15,18(35),31-hexaen-22-yl]butylamino]-3-oxopropoxy]ethoxy]ethoxy]ethoxy]ethyl]pentanamide
• CAS: 1453168-14-3
• 化学式: C₅₈H₇₈N₁₂O₁₃S₃
• 分子量: 1247.53
• InChiKey: HMEYUEAGPRJHNL-OHJCNVAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  86
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  398
• 氢给体数：
  7
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  乙基2-[(1S)-1-氨基乙基]-1,3-噻唑-4-羧酸酯 在 氢溴酸 、 双氧水 、 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 溶剂黄146 、 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 、 lithium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[2-[2-[2-[2-[3-[4-[(6S,12R,19S,22S,25S)-12-benzyl-19-methyl-11,14,21,24,30-pentaoxo-33-oxa-4,17-dithia-10,13,20,23,29,34,35,36-octazahexacyclo[29.2.1.12,5.115,18.06,10.025,29]hexatriaconta-1(34),2,5(36),15,18(35),31-hexaen-22-yl]butylamino]-3-oxopropoxy]ethoxy]ethoxy]ethoxy]ethyl]pentanamide
  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

文献信息

• Mechanistic Studies of Sanguinamide B Derivatives: A Unique Inhibitor of Eukaryotic Ribosomes
  作者：Worawan Tantisantisom、Deborah M. Ramsey、Shelli R. McAlpine

  DOI：10.1021/ol401749p

  日期：2013.9.20

  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.