4-(5-amino-2-(2,4,6-trichlorophenoxy)pyrimidin-4-ylamino)benzonitrile | 1533448-24-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(5-amino-2-(2,4,6-trichlorophenoxy)pyrimidin-4-ylamino)benzonitrile
• 英文别名: 4-[[5-Amino-2-(2,4,6-trichlorophenoxy)pyrimidin-4-yl]amino]benzonitrile；4-[[5-amino-2-(2,4,6-trichlorophenoxy)pyrimidin-4-yl]amino]benzonitrile
• CAS: 1533448-24-6
• 化学式: C₁₇H₁₀Cl₃N₅O
• 分子量: 406.658
• InChiKey: PIQHVSIXQYXXCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(5-amino-2-(2,4,6-trichlorophenoxy)pyrimidin-4-ylamino)benzonitrile 、 三氟乙酸酐 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以41.2%的产率得到N-(4-(4-cyanophenylamino)-2-(2,4,6-trichlorophenoxy)pyrimidin-5-yl)-2,2,2-trifluoroacetamide
  参考文献：
  名称：

  Discovery of novel diarylpyrimidines as potent HIV NNRTIs via a structure-guided core-refining approach

  摘要：

  Guided by crystal structures of HIV-1 RT/DAPY complex and molecular modeling studies, a series of novel DAPY derivatives were rationally designed, synthesized and evaluated for their anti-HIV activities. Among them, 16 compounds significantly inhibited HIV-1 IIIB replication with EC50 values lower than 66 nM. Particularly, compound 7a was the most potent inhibitor against HIV-1 wild-type and double RT mutant HIV-1 strain K103N/Y181C, with an EC50 value of 2.5 nM (SI = 13,740) and 0.33 μM (SI = 107), respectively. Unexpectedly, compound 8c was found to show moderate anti-HIV-2 potency (EC50 = 5.57 μM). Preliminary structure-activity relationships (SARs) and molecular modeling of these new analogues were also discussed in detail.

  DOI：

  10.1016/j.ejmech.2014.04.036
• 作为产物：
  描述：

  4-(2-chloro-5-nitropyrimidin-4-ylamino)benzonitrile 在 tin(II) chloride dihdyrate 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 4-(5-amino-2-(2,4,6-trichlorophenoxy)pyrimidin-4-ylamino)benzonitrile
  参考文献：
  名称：

  Discovery of novel diarylpyrimidines as potent HIV NNRTIs via a structure-guided core-refining approach

  摘要：

  Guided by crystal structures of HIV-1 RT/DAPY complex and molecular modeling studies, a series of novel DAPY derivatives were rationally designed, synthesized and evaluated for their anti-HIV activities. Among them, 16 compounds significantly inhibited HIV-1 IIIB replication with EC50 values lower than 66 nM. Particularly, compound 7a was the most potent inhibitor against HIV-1 wild-type and double RT mutant HIV-1 strain K103N/Y181C, with an EC50 value of 2.5 nM (SI = 13,740) and 0.33 μM (SI = 107), respectively. Unexpectedly, compound 8c was found to show moderate anti-HIV-2 potency (EC50 = 5.57 μM). Preliminary structure-activity relationships (SARs) and molecular modeling of these new analogues were also discussed in detail.

  DOI：

  10.1016/j.ejmech.2014.04.036

文献信息

• Discovery of novel diarylpyrimidines as potent HIV NNRTIs via a structure-guided core-refining approach
  作者：Xiao Li、Wenmin Chen、Ye Tian、Huiqing Liu、Peng Zhan、Erik De Clercq、Christophe Pannecouque、Jan Balzarini、Xinyong Liu

  DOI：10.1016/j.ejmech.2014.04.036

  日期：2014.6

  Guided by crystal structures of HIV-1 RT/DAPY complex and molecular modeling studies, a series of novel DAPY derivatives were rationally designed, synthesized and evaluated for their anti-HIV activities. Among them, 16 compounds significantly inhibited HIV-1 IIIB replication with EC50 values lower than 66 nM. Particularly, compound 7a was the most potent inhibitor against HIV-1 wild-type and double RT mutant HIV-1 strain K103N/Y181C, with an EC50 value of 2.5 nM (SI = 13,740) and 0.33 μM (SI = 107), respectively. Unexpectedly, compound 8c was found to show moderate anti-HIV-2 potency (EC50 = 5.57 μM). Preliminary structure-activity relationships (SARs) and molecular modeling of these new analogues were also discussed in detail.