4-[[4-amino-6-[(1R)-1-(2,6-difluorophenyl)ethyl]-5-methylpyrimidin-2-yl]amino]benzonitrile | 1364318-44-4

• 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: 4-[[4-amino-6-[(1R)-1-(2,6-difluorophenyl)ethyl]-5-methylpyrimidin-2-yl]amino]benzonitrile
• CAS: 1364318-44-4
• 化学式: C₂₀H₁₇F₂N₅
• 分子量: 365.385
• InChiKey: NLLCUFSLYCPCOQ-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  87.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-(4-amino-6-(1-(2,6-difluorophenyl)ethyl)-5-methylpyrimidin-2-ylamino)benzonitrile 在 Chiralpak AD column 作用下， 以 乙醇 、 二乙胺 为溶剂， 生成 4-[[4-amino-6-[(1R)-1-(2,6-difluorophenyl)ethyl]-5-methylpyrimidin-2-yl]amino]benzonitrile 、 4-[[4-amino-6-[(1S)-1-(2,6-difluorophenyl)ethyl]-5-methylpyrimidin-2-yl]amino]benzonitrile
  参考文献：
  名称：

  2-(Alkyl/Aryl)Amino-6-Benzylpyrimidin-4(3H)-ones as Inhibitors of Wild-Type and Mutant HIV-1: Enantioselectivity Studies

  摘要：

  The single enantiomers of two pyrimidine-based HIV-1 non-nucleoside reverse transcriptase inhibitors, 1 (MC1501) and 2 (MC2082), were tested in both cellular and enzyme assays. In general, the R forms were more potent than their S counterparts and racemates and (R)-2 was more efficient than (R)-1 and the reference compounds, with some exceptions. Interestingly, (R)-2 displayed a faster binding to K103N RT with respect to WT RT, while (R)-1 showed the opposite behavior.

  DOI：

  10.1021/jm201308v

文献信息

• 2-(Alkyl/Aryl)Amino-6-Benzylpyrimidin-4(3<i>H</i>)-ones as Inhibitors of Wild-Type and Mutant HIV-1: Enantioselectivity Studies
  作者：Dante Rotili、Alberta Samuele、Domenico Tarantino、Rino Ragno、Ira Musmuca、Flavio Ballante、Giorgia Botta、Ludovica Morera、Marco Pierini、Roberto Cirilli、Maxim B. Nawrozkij、Emmanuel Gonzalez、Bonaventura Clotet、Marino Artico、José A. Esté、Giovanni Maga、Antonello Mai

  DOI：10.1021/jm201308v

  日期：2012.4.12

  The single enantiomers of two pyrimidine-based HIV-1 non-nucleoside reverse transcriptase inhibitors, 1 (MC1501) and 2 (MC2082), were tested in both cellular and enzyme assays. In general, the R forms were more potent than their S counterparts and racemates and (R)-2 was more efficient than (R)-1 and the reference compounds, with some exceptions. Interestingly, (R)-2 displayed a faster binding to K103N RT with respect to WT RT, while (R)-1 showed the opposite behavior.