((3S,6S,7S,9aS)-3-(benzhydrylcarbamoyl)-6-((S)-2-((tert-butoxycarbonyl)(methyl)amino)butanamido)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepin-7-yl)methyl methanesulfonate | 1366595-90-5

• 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: ((3S,6S,7S,9aS)-3-(benzhydrylcarbamoyl)-6-((S)-2-((tert-butoxycarbonyl)(methyl)amino)butanamido)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepin-7-yl)methyl methanesulfonate
• CAS: 1366595-90-5
• 化学式: C₃₅H₄₈N₄O₈S
• 分子量: 684.854
• InChiKey: XRJKIOFDGFWWDQ-QUBFWBSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  48.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  151.42
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ((3S,6S,7S,9aS)-3-(benzhydrylcarbamoyl)-6-((S)-2-((tert-butoxycarbonyl)(methyl)amino)butanamido)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepin-7-yl)methyl methanesulfonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以810 mg的产率得到tert-butyl N-[(2S)-1-[[(3S,6S,7R,9aS)-7-(azidomethyl)-3-(benzhydrylcarbamoyl)-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepin-6-yl]amino]-1-oxobutan-2-yl]-N-methylcarbamate
  参考文献：
  名称：

  Rational design, synthesis and characterization of potent, non-peptidic Smac mimics/XIAP inhibitors as proapoptotic agents for cancer therapy

  摘要：

  Novel proapoptotic Smac mimics/IAPs inhibitors have been designed, synthesized and characterized. Computational models and structural studies (crystallography, NMR) have elucidated the SAR of this class of inhibitors, and have permitted further optimization of their properties. In vitro characterization (XIAP BIR3 and linker-BIR2-BIR3 binding, cytotox assays, early ADMET profiling) of the compounds has been performed, identifying one lead for further in vitro and in vivo evaluation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.009
• 作为产物：
  描述：

  tert-butyl N-[(2S)-1-[[(3S,6S,7S,9aS)-3-(benzhydrylcarbamoyl)-7-(hydroxymethyl)-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepin-6-yl]amino]-1-oxobutan-2-yl]-N-methylcarbamate 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 ((3S,6S,7S,9aS)-3-(benzhydrylcarbamoyl)-6-((S)-2-((tert-butoxycarbonyl)(methyl)amino)butanamido)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepin-7-yl)methyl methanesulfonate
  参考文献：
  名称：

  Rational design, synthesis and characterization of potent, non-peptidic Smac mimics/XIAP inhibitors as proapoptotic agents for cancer therapy

  摘要：

  Novel proapoptotic Smac mimics/IAPs inhibitors have been designed, synthesized and characterized. Computational models and structural studies (crystallography, NMR) have elucidated the SAR of this class of inhibitors, and have permitted further optimization of their properties. In vitro characterization (XIAP BIR3 and linker-BIR2-BIR3 binding, cytotox assays, early ADMET profiling) of the compounds has been performed, identifying one lead for further in vitro and in vivo evaluation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.009