diallyl (2S,5'S)-5'-benzyl-5'-(((4S,5S)-4-benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-5-yl)methyl)-4-((R)-1-((tert-butyldimethylsilyl)oxy)-3-phenylpropan-2-yl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3'-bipyrrole]-1,1'-dicarboxylate | 173091-89-9

• 分子结构分类: 有机化合物
• 英文名称: diallyl (2S,5'S)-5'-benzyl-5'-(((4S,5S)-4-benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-5-yl)methyl)-4-((R)-1-((tert-butyldimethylsilyl)oxy)-3-phenylpropan-2-yl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3'-bipyrrole]-1,1'-dicarboxylate
• CAS: 173091-89-9
• 化学式: C₆₀H₇₉N₃O₁₀Si
• 分子量: 1030.39
• InChiKey: CUDGYUAAAPWBGS-RONYUJNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.19
• 重原子数：
  74.0
• 可旋转键数：
  19.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  141.22
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  diallyl (2S,5'S)-5'-benzyl-5'-(((4S,5S)-4-benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-5-yl)methyl)-4-((R)-1-((tert-butyldimethylsilyl)oxy)-3-phenylpropan-2-yl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3'-bipyrrole]-1,1'-dicarboxylate 在 盐酸 、 四(三苯基膦)钯 、 jones reagent 、 氨 、 5,5-二甲基-1,3-环己二酮 、 三乙胺 、 乙酰氯 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 30.17h， 生成 (2R)-2-[(5S)-5-[(5S)-5-[(2S,3S)-3-amino-2-hydroxy-4-phenylbutyl]-5-benzyl-4-oxo-1H-pyrrol-3-yl]-5-(2-methylpropyl)-4-oxo-1H-pyrrol-3-yl]-3-phenylpropanamide
  参考文献：
  名称：

  Pyrrolinone-Based HIV Protease Inhibitors. Design, Synthesis, and Antiviral Activity: Evidence for Improved Transport

  摘要：

  Pyrrolinone-based peptidomimetics, the first mimics of beta-strands, are potent inhibitors of HIV-1 protease. Importantly, the bis(pyrrolinones) described herein proved to be more active in cellular antiviral assays compared with an analogous peptide-derived inhibitor even though they are less effective in inhibiting the isolated protease. These results suggest that pyrrolinone inhibitors offer better transport properties than the corresponding peptide-based peptidomimetics; we attribute this effect to decreased solvation of the mimetics. Structure-activity relationships for the pyrrolinones correlate well with those reported for related peptides, consistent with similar modes of binding.

  DOI：

  10.1021/ja00150a011
• 作为产物：
  描述：

  在 四(三苯基膦)钯 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 5,5-二甲基-1,3-环己二酮 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.5h， 生成 diallyl (2S,5'S)-5'-benzyl-5'-(((4S,5S)-4-benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-5-yl)methyl)-4-((R)-1-((tert-butyldimethylsilyl)oxy)-3-phenylpropan-2-yl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3'-bipyrrole]-1,1'-dicarboxylate
  参考文献：
  名称：

  Pyrrolinone-Based HIV Protease Inhibitors. Design, Synthesis, and Antiviral Activity: Evidence for Improved Transport

  摘要：

  Pyrrolinone-based peptidomimetics, the first mimics of beta-strands, are potent inhibitors of HIV-1 protease. Importantly, the bis(pyrrolinones) described herein proved to be more active in cellular antiviral assays compared with an analogous peptide-derived inhibitor even though they are less effective in inhibiting the isolated protease. These results suggest that pyrrolinone inhibitors offer better transport properties than the corresponding peptide-based peptidomimetics; we attribute this effect to decreased solvation of the mimetics. Structure-activity relationships for the pyrrolinones correlate well with those reported for related peptides, consistent with similar modes of binding.

  DOI：

  10.1021/ja00150a011