benzyl N-[(2S)-1-[[(2S)-1-[[(1S)-1-[(4R,5R)-2,2-dimethyl-5-[(1S)-3-methyl-1-[[(2S)-3-methyl-2-[[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]amino]butanoyl]amino]butyl]-1,3-dioxolan-4-yl]-3-methylbutyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]carbamate | 222848-18-2

• 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: benzyl N-[(2S)-1-[[(2S)-1-[[(1S)-1-[(4R,5R)-2,2-dimethyl-5-[(1S)-3-methyl-1-[[(2S)-3-methyl-2-[[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]amino]butanoyl]amino]butyl]-1,3-dioxolan-4-yl]-3-methylbutyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]carbamate
• CAS: 222848-18-2
• 化学式: C₄₇H₇₂N₆O₁₀
• 分子量: 881.123
• InChiKey: RCIIDCNNRPPMTD-MEPBAOBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  63.0
• 可旋转键数：
  22.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  211.52
• 氢给体数：
  6.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  benzyl N-[(2S)-1-[[(2S)-1-[[(1S)-1-[(4R,5R)-2,2-dimethyl-5-[(1S)-3-methyl-1-[[(2S)-3-methyl-2-[[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]amino]butanoyl]amino]butyl]-1,3-dioxolan-4-yl]-3-methylbutyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]carbamate 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以57%的产率得到(2S)-N-[4-((2S)-2-{(2S)-2-[(Phenylmethoxy)carbonylamino]propanoylamino}-3-methylbutanoylamino)(1S,4S,2R,3R)-2,3-dihydroxy-6-methyl-1-(2-methylpropyl)heptyl]-2-{(2S)-2-[(phenylmethoxy)carbonylamino]propanoylamino}-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
• 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 45.5h， 生成 benzyl N-[(2S)-1-[[(2S)-1-[[(1S)-1-[(4R,5R)-2,2-dimethyl-5-[(1S)-3-methyl-1-[[(2S)-3-methyl-2-[[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]amino]butanoyl]amino]butyl]-1,3-dioxolan-4-yl]-3-methylbutyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]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