{(1S,2S,4R)-1-Benzyl-4-[(S)-1-(3-dimethylamino-propylcarbamoyl)-2-methyl-butylcarbamoyl]-2-hydroxy-5-phenyl-pentyl}-carbamic acid tert-butyl ester | 126409-50-5

• 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: {(1S,2S,4R)-1-Benzyl-4-[(S)-1-(3-dimethylamino-propylcarbamoyl)-2-methyl-butylcarbamoyl]-2-hydroxy-5-phenyl-pentyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S,3S,5R)-5-benzyl-5-{[(1S,2S)-1-{[3-(dimethylamino)propyl]carbamoyl}-2-methylbutyl]carbamoyl}-3-hydroxy-1-phenylpentan-2-yl]carbamate；tert-butyl N-[(2S,3S,5R)-5-benzyl-6-[[(2S)-1-[3-(dimethylamino)propylamino]-3-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-6-oxo-1-phenylhexan-2-yl]carbamate
• CAS: 126409-50-5
• 化学式: C₃₅H₅₄N₄O₅
• 分子量: 610.838
• InChiKey: OMFXTEYPVOHXHU-MZHARIFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  44
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (S)-2-[(2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoylamino]-3-methyl-pentanoic acid methyl ester 在 lithium hydroxide 、 四丁基氟化铵 、 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 四氢呋喃 、 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-4-[(S)-1-(3-dimethylamino-propylcarbamoyl)-2-methyl-butylcarbamoyl]-2-hydroxy-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

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.