benzyl (S)-3-((S)-2-(2-(tert-butoxy)-2-oxoacetamido)propanamido)-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoate | 1119252-51-5

• 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: benzyl (S)-3-((S)-2-(2-(tert-butoxy)-2-oxoacetamido)propanamido)-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoate
• CAS: 1119252-51-5
• 化学式: C₂₇H₂₈F₄N₂O₈
• 分子量: 584.522
• InChiKey: BAXXBPZYOYTIBU-KSSFIOAISA-N

物化性质

• 密度：
  1.331±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  41.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  137.1
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  benzyl (S)-3-((S)-2-(2-(tert-butoxy)-2-oxoacetamido)propanamido)-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到2-(((S)-1-(((S)-1-(benzyloxy)-1,4-dioxo-5-(2,3,5,6-tetrafluorophenoxy)pentan-3-yl)amino)-1-oxopropan-2-yl)amino)-2-oxoacetic acid
  参考文献：
  名称：

  Synthesis and structure–activity relationships of oxamyl dipeptide caspase inhibitors developed for the treatment of liver disease

  摘要：

  The P4 region of a series of oxamyl dipeptide caspase inhibitors was optimized by the combination of anti-apoptotic activity in the Jurkat/Fas (JFas) cellular assay and membrane permeability in the PAMPA assay. Two highly potent anti-apoptotic agents with moderate membrane permeability, 29 and 36, showed strong in vivo efficacy in a murine model of alpha-Fas-induced liver injury. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.117
• 作为产物：
  描述：

  benzyl (S)-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoate hydrochloride 、 (2S)-2-[[2-[(2-methylpropan-2-yl)oxy]-2-oxoacetyl]amino]propanoic acid 在 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-) 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以50%的产率得到benzyl (S)-3-((S)-2-(2-(tert-butoxy)-2-oxoacetamido)propanamido)-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of oxamyl dipeptide caspase inhibitors developed for the treatment of liver disease

  摘要：

  The P4 region of a series of oxamyl dipeptide caspase inhibitors was optimized by the combination of anti-apoptotic activity in the Jurkat/Fas (JFas) cellular assay and membrane permeability in the PAMPA assay. Two highly potent anti-apoptotic agents with moderate membrane permeability, 29 and 36, showed strong in vivo efficacy in a murine model of alpha-Fas-induced liver injury. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.117