<5(S)-<(tert-butoxycarbonyl)amino>-4(S)-(tertbutyldimethylsiloxy)-6-phenyl-2(R)-(phenylmethyl)hexanoyl>valine amide | 135832-74-5

• 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: <5(S)-<(tert-butoxycarbonyl)amino>-4(S)-(tertbutyldimethylsiloxy)-6-phenyl-2(R)-(phenylmethyl)hexanoyl>valine amide
• 英文别名: tert-butyl N-[(1S,2S,4R)-1,4-dibenzyl-2-[tert-butyl(dimethyl)silyl]oxy-5-[[(1S)-1-carbamoyl-2-methyl-propyl]amino]-5-oxo-pentyl]carbamate；tert-butyl N-[(2S,3S,5R)-6-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]amino]-5-benzyl-3-[tert-butyl(dimethyl)silyl]oxy-6-oxo-1-phenylhexan-2-yl]carbamate
• CAS: 135832-74-5
• 化学式: C₃₅H₅₅N₃O₅Si
• 分子量: 625.924
• InChiKey: IJJOCHJGVPDCSG-RYTSNQFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.39
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  <5(S)-<(tert-butoxycarbonyl)amino>-4(S)-(tertbutyldimethylsiloxy)-6-phenyl-2(R)-(phenylmethyl)hexanoyl>valine amide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 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：

  L-缬氨酰胺盐酸盐 、 N-(1,1-dimethylethoxycarbonyl)-5(S)-amino-4(S)-(t-butyldimethylsilyloxy)-6-phenyl-2(R)-(phenylmethyl)hexanoic acid 在 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 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以0.24 g的产率得到<5(S)-<(tert-butoxycarbonyl)amino>-4(S)-(tertbutyldimethylsiloxy)-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