(4S,5S)-4-Benzyl-5-[(2S,5'S)-5'-benzyl-4-((R)-1-carbamoyl-2-phenyl-ethyl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-5'-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 173091-91-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (4S,5S)-4-Benzyl-5-[(2S,5'S)-5'-benzyl-4-((R)-1-carbamoyl-2-phenyl-ethyl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-5'-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS: 173091-91-3
• 化学式: C₄₆H₅₆N₄O₆
• 分子量: 760.974
• InChiKey: KNJPQMGWDMKWSS-CLEHCZRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.58
• 重原子数：
  56.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  140.06
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-Benzyl-5-[(2S,5'S)-5'-benzyl-4-((R)-1-carbamoyl-2-phenyl-ethyl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-5'-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 盐酸 、 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以84%的产率得到(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 氨 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 (4S,5S)-4-Benzyl-5-[(2S,5'S)-5'-benzyl-4-((R)-1-carbamoyl-2-phenyl-ethyl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-5'-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  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