((S)-1-{(S)-1-[(1S,2R)-1-Benzyl-3-((S)-2-tert-butylcarbamoyl-pyrrolidin-1-yl)-2-hydroxy-propylcarbamoyl]-2-methyl-propylcarbamoyl}-ethyl)-carbamic acid benzyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ((S)-1-{(S)-1-[(1S,2R)-1-Benzyl-3-((S)-2-tert-butylcarbamoyl-pyrrolidin-1-yl)-2-hydroxy-propylcarbamoyl]-2-methyl-propylcarbamoyl}-ethyl)-carbamic acid benzyl ester
• 英文别名: (2S)-N-(3-{(2S)-2-[N-(tert-Butyl)carbamoyl]pyrrolidinyl}(1S,2R)-2-hydroxy-1-benzylpropyl)-2-{(2S)-2-[(phenylmethoxy)carbonylamino]propanoylamino}-3-methylbutanamide；benzyl N-[(2S)-1-[[(2S)-1-[[(2S,3R)-4-[(2S)-2-(tert-butylcarbamoyl)pyrrolidin-1-yl]-3-hydroxy-1-phenylbutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]carbamate
• 化学式: C₃₅H₅₁N₅O₆
• 分子量: 637.82
• InChiKey: AUORYIJXDZVIBG-FKHUNUEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  149
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  Z-Phe-O-COO-isoBu 在 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 氢气 、 sodium methylate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 、 乙腈 为溶剂， 反应 0.25h， 生成 ((S)-1-{(S)-1-[(1S,2R)-1-Benzyl-3-((S)-2-tert-butylcarbamoyl-pyrrolidin-1-yl)-2-hydroxy-propylcarbamoyl]-2-methyl-propylcarbamoyl}-ethyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Development of a New Type of Protease Inhibitors, Efficacious against FIV and HIV Variants

  摘要：

  Based on the structural analysis of FIV protease and drug-resistant HIV proteases and molecular modeling, a new type of inhibitors with a small P3 residue has been developed. These inhibitors are effective against HIV and its drug-resistant mutants, as well as SIV and FIV. Modification of existing HIV protease inhibitors by reducing the size of the P3 residue has the same effect. This finding provides a new strategy for the development of HIV protease inhibitors effective against the wild-type and drug-resistant mutants. It further supports the use of FIV protease as a useful model for drug-resistant HIV proteases, which often have a more constricted binding region for the P3 group or the combined P3 and P1 groups.

  DOI：

  10.1021/ja982893p

文献信息

• Development of a New Type of Protease Inhibitors, Efficacious against FIV and HIV Variants
  作者：Taekyu Lee、Van-Duc Le、Dongyeol Lim、Ying-Chuan Lin、Garrett M. Morris、Andrew L. Wong、Arthur J. Olson、John H. Elder、Chi-Huey Wong

  DOI：10.1021/ja982893p

  日期：1999.2.1

  Based on the structural analysis of FIV protease and drug-resistant HIV proteases and molecular modeling, a new type of inhibitors with a small P3 residue has been developed. These inhibitors are effective against HIV and its drug-resistant mutants, as well as SIV and FIV. Modification of existing HIV protease inhibitors by reducing the size of the P3 residue has the same effect. This finding provides a new strategy for the development of HIV protease inhibitors effective against the wild-type and drug-resistant mutants. It further supports the use of FIV protease as a useful model for drug-resistant HIV proteases, which often have a more constricted binding region for the P3 group or the combined P3 and P1 groups.