3-(benzyloxy)-4-(3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propoxy)phenoxy)benzonitrile | 1351862-21-9

• 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: 3-(benzyloxy)-4-(3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propoxy)phenoxy)benzonitrile
• CAS: 1351862-21-9
• 化学式: C₂₈H₂₉NO₅
• 分子量: 459.542
• InChiKey: LKAZTTXXKWGJFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.24
• 重原子数：
  34.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  69.94
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-(benzyloxy)-4-(3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propoxy)phenoxy)benzonitrile 在 ammonium hydroxide 、 偶氮二甲酸二异丙酯 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-[2-(2,4-Dioxopyrimidin-1-yl)ethoxy]-4-[3-[3-(oxan-2-yloxy)propoxy]phenoxy]benzonitrile
  参考文献：
  名称：

  Computationally-Guided Optimization of a Docking Hit to Yield Catechol Diethers as Potent Anti-HIV Agents

  摘要：

  A 5-mu M docking hit has been optimized to an extraordinarily potent (55 pM) non-nucleoside inhibitor of HIV reverse transcriptase. Use of free energy perturbation (PEP) calculations to predict relative free energies of binding aided the optimizations by identifying optimal substitution patterns for phenyl rings and a linker. The most potent resultant catechol diethers feature terminal uracil and cyanovinylphenyl groups. A halogen bond with Pro95 likely contributes to the extreme potency of compound 42. In addition, several examples are provided illustrating failures of attempted grafting of a substructure from a very active compound onto a seemingly related scaffold to improve its activity.

  DOI：

  10.1021/jm201134m
• 作为产物：
  描述：

  4-氟-3-甲氧基苯腈 在 sodium hydride 、 potassium carbonate 、 lithium chloride 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.17h， 生成 3-(benzyloxy)-4-(3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propoxy)phenoxy)benzonitrile
  参考文献：
  名称：

  Computationally-Guided Optimization of a Docking Hit to Yield Catechol Diethers as Potent Anti-HIV Agents

  摘要：

  A 5-mu M docking hit has been optimized to an extraordinarily potent (55 pM) non-nucleoside inhibitor of HIV reverse transcriptase. Use of free energy perturbation (PEP) calculations to predict relative free energies of binding aided the optimizations by identifying optimal substitution patterns for phenyl rings and a linker. The most potent resultant catechol diethers feature terminal uracil and cyanovinylphenyl groups. A halogen bond with Pro95 likely contributes to the extreme potency of compound 42. In addition, several examples are provided illustrating failures of attempted grafting of a substructure from a very active compound onto a seemingly related scaffold to improve its activity.

  DOI：

  10.1021/jm201134m

文献信息

• [EN] CATECHOL DIETHERS AS POTENT ANTI-HIV AGENTS<br/>[FR] DIÉTHERS DE CATÉCHOL COMME AGENTS ANTI-HIV PUISSANTS
  申请人：UNIV YALE

  公开号：WO2013056003A3

  公开（公告）日：2013-06-20