N-{5(S)-[(tert-butoxycarbonyl)amino]-4(S)-(tert-butyldimethylsiloxy)-6-phenyl-2(R)-(phenylmethyl)hexanoyl}valine methyl ester | 135832-58-5

• 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: N-{5(S)-[(tert-butoxycarbonyl)amino]-4(S)-(tert-butyldimethylsiloxy)-6-phenyl-2(R)-(phenylmethyl)hexanoyl}valine methyl ester
• 英文别名: methyl (2S)-2-[[(2R,4S,5S)-2-benzyl-4-[tert-butyl(dimethyl)silyl]oxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-phenylhexanoyl]amino]-3-methylbutanoate
• CAS: 135832-58-5
• 化学式: C₃₆H₅₆N₂O₆Si
• 分子量: 640.936
• InChiKey: JSOVZYSSXJMBSV-BHSUFKTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.08
• 重原子数：
  45
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-{5(S)-[(tert-butoxycarbonyl)amino]-4(S)-(tert-butyldimethylsiloxy)-6-phenyl-2(R)-(phenylmethyl)hexanoyl}valine methyl ester 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 19.0h， 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
• 作为产物：
  描述：

  L-缬氨酸甲酯盐酸盐 、 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100%的产率得到N-{5(S)-[(tert-butoxycarbonyl)amino]-4(S)-(tert-butyldimethylsiloxy)-6-phenyl-2(R)-(phenylmethyl)hexanoyl}valine methyl 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

文献信息

• Design and synthesis of HIV protease inhibitors. Variations of the carboxyterminus of the HIV protease inhibitor L-682,679
  作者：S. Jane DeSolms、Elizabeth A. Giuliani、James P. Guare、Joseph P. Vacca、William M. Sanders、Samuel L. Graham、J. Mark Wiggins、Paul L. Darke、Irving S. Sigal

  DOI：10.1021/jm00113a025

  日期：1991.9

  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.