{(1S,2S,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-2-methyl-1-(3-morpholin-4-yl-propylcarbamoyl)-propylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester | 135832-75-6

• 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: {(1S,2S,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-2-methyl-1-(3-morpholin-4-yl-propylcarbamoyl)-propylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester
• CAS: 135832-75-6
• 化学式: C₄₂H₆₈N₄O₆Si
• 分子量: 753.111
• InChiKey: XTPZYCMDRMGQSL-HQPLKVBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.74
• 重原子数：
  53.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  118.23
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  {(1S,2S,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-2-methyl-1-(3-morpholin-4-yl-propylcarbamoyl)-propylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以81%的产率得到N'-(3-morpholinopropyl)-N-{5(S)-[(tert-butoxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2(R)-(phenylmethyl)hexanoyl}valine amide
  参考文献：
  名称：

  Design and synthesis of HIV protease inhibitors. Variations of the carboxyterminus of the HIV protease inhibitor L-682,679

  摘要：

  A series of tetrapeptide analogues of 1 (L-682,679), in which the carboxy terminus has been shortened and modified, was prepared and their inhibitory activity measured against the HIV protease in a peptide cleavage assay. Selected examples were tested as inhibitors of virus spread in cell culture. Compound 12 was a 10-fold more potent enzyme inhibitor than 1 in vitro and 30-fold more potent in inhibiting the viral spread in cells.

  DOI：

  10.1021/jm00113a025
• 作为产物：
  描述：

  N-(1,1-dimethylethoxycarbonyl)-5(S)-amino-4(S)-(t-butyldimethylsilyloxy)-6-phenyl-2(R)-(phenylmethyl)hexanoic acid 在 lithium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 {(1S,2S,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-2-methyl-1-(3-morpholin-4-yl-propylcarbamoyl)-propylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Design and synthesis of HIV protease inhibitors. Variations of the carboxyterminus of the HIV protease inhibitor L-682,679

  摘要：

  A series of tetrapeptide analogues of 1 (L-682,679), in which the carboxy terminus has been shortened and modified, was prepared and their inhibitory activity measured against the HIV protease in a peptide cleavage assay. Selected examples were tested as inhibitors of virus spread in cell culture. Compound 12 was a 10-fold more potent enzyme inhibitor than 1 in vitro and 30-fold more potent in inhibiting the viral spread in cells.

  DOI：

  10.1021/jm00113a025