{(S)-4-[(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-phenyl-ethyl]-2-isobutyl-3-oxo-2,3-dihydro-1H-pyrrol-2-yl}-acetaldehyde | 173091-86-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: {(S)-4-[(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-phenyl-ethyl]-2-isobutyl-3-oxo-2,3-dihydro-1H-pyrrol-2-yl}-acetaldehyde
• CAS: 173091-86-6
• 化学式: C₂₅H₃₉NO₃Si
• 分子量: 429.675
• InChiKey: URVIKHUSRKDNMG-SQJMNOBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  {(S)-4-[(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-phenyl-ethyl]-2-isobutyl-3-oxo-2,3-dihydro-1H-pyrrol-2-yl}-acetaldehyde 在 盐酸 、 四(三苯基膦)钯 、 jones reagent 、 氨 、 双(三甲基硅烷基)氨基钾 、 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 、 氯仿 、 甲苯 、 乙腈 为溶剂， 反应 34.67h， 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：

  (S)-2-benzyl-5-methyl-hex-4-en-1-ol 在 咪唑 、 lead(IV) acetate 、 sodium hydroxide 、 四氧化锇 、 N-甲基吲哚酮 、 双(三甲基硅烷基)氨基钾 、 臭氧 、 三苯基膦 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.75h， 生成 {(S)-4-[(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-phenyl-ethyl]-2-isobutyl-3-oxo-2,3-dihydro-1H-pyrrol-2-yl}-acetaldehyde
  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