(2S)-2-amino-N-[(1S)-1-[(4R,5R)-5-[(1S)-1-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-methylbutyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbutyl]-3-methylbutanamide | 222848-11-5

• 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: (2S)-2-amino-N-[(1S)-1-[(4R,5R)-5-[(1S)-1-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-methylbutyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbutyl]-3-methylbutanamide
• CAS: 222848-11-5
• 化学式: C₂₅H₅₀N₄O₄
• 分子量: 470.696
• InChiKey: IBTWBZNECHOSGM-PCPGVINSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  33.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  128.7
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S)-2-amino-N-[(1S)-1-[(4R,5R)-5-[(1S)-1-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-methylbutyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbutyl]-3-methylbutanamide 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 24.25h， 生成 benzyl N-[(1S)-1-[[(1S)-1-[[(1S,2R,3R,4S)-4-[[(2S)-2-[[(2S)-2-(benzyloxycarbonylamino)-4-methyl-pentanoyl]amino]-3-methyl-butanoyl]amino]-2,3-dihydroxy-1-isobutyl-6-methyl-heptyl]carbamoyl]-2-methyl-propyl]carbamoyl]-3-methyl-butyl]carbamate
  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
• 作为产物：
  描述：

  (4-benzyloxycarbonylamino-2,3-dihydroxy-1-isobutyl-6-methyl-heptyl)-carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 45.25h， 生成 (2S)-2-amino-N-[(1S)-1-[(4R,5R)-5-[(1S)-1-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-methylbutyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbutyl]-3-methylbutanamide
  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