{1-[5-(1-benzyloxycarbonylamino-3-methyl-butyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-methyl-butyl}-carbamic acid benzyl ester | 142285-44-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: {1-[5-(1-benzyloxycarbonylamino-3-methyl-butyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-methyl-butyl}-carbamic acid benzyl ester
• CAS: 142285-44-7
• 化学式: C₃₁H₄₄N₂O₆
• 分子量: 540.7
• InChiKey: NBTCGWZOIXEJNI-YVHASNINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.19
• 重原子数：
  39.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  95.12
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  {1-[5-(1-benzyloxycarbonylamino-3-methyl-butyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-methyl-butyl}-carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 40.5h， 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)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]butanoyl]amino]butyl]-1,3-dioxolan-4-yl]-3-methylbutyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-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
• 作为产物：
  描述：

  (4-benzyloxycarbonylamino-2,3-dihydroxy-1-isobutyl-6-methyl-heptyl)-carbamic acid benzyl ester 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以50%的产率得到{1-[5-(1-benzyloxycarbonylamino-3-methyl-butyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-methyl-butyl}-carbamic acid benzyl ester
  参考文献：
  名称：

  Expedient solid-phase synthesis of both symmetric and asymmetric diol libraries targeting aspartic proteases

  摘要：

  C-2-symmetric diols have been shown to be highly potent against HIV-1 protease (PR). However, gaining access to these compounds has been hampered by the need of multistep solution-phase reactions which are often tedious and inefficient. In this Letter, we have disclosed a solid-phase strategy for rapid preparation of small molecule-based, symmetric and asymmetric diols as potential HIV-1 protease inhibitors. Upon biological screening, we found one of them, SYM-5, to be a potent and selective inhibitor (K-i = 400 nM) against HIV-1 protease. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.041