2-tert-butyl-N-[(4-fluorophenyl)methyl]-5,6-dihydroxy-pyrimidine-4-carboxamide | 940315-31-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-tert-butyl-N-[(4-fluorophenyl)methyl]-5,6-dihydroxy-pyrimidine-4-carboxamide
• 英文别名: 2-tert-butyl-N-[(4-fluorophenyl)methyl]-5-hydroxy-6-oxo-1H-pyrimidine-4-carboxamide
• CAS: 940315-31-1
• 化学式: C₁₆H₁₈FN₃O₃
• 分子量: 319.336
• InChiKey: UJZVTGOPYAKBIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  90.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  三甲基乙腈 在 盐酸羟胺 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成 2-tert-butyl-N-[(4-fluorophenyl)methyl]-5,6-dihydroxy-pyrimidine-4-carboxamide
  参考文献：
  名称：

  Design and synthesis of novel pyrimidone analogues as HIV-1 integrase inhibitors

  摘要：

  A series of novel pyrimidone analogues have been designed and synthesized as HIV-1 integrase (IN) inhibitors. This study demonstrated that introducing a substituent in the N1-position of the pyrimidone scaffold does not significantly influence IN inhibitory activity. Molecular docking studies showed these compounds could occupy the IN active site and form pi-pi interactions with viral DNA nucleotides DC16 and DA17 to displace reactive viral DNA 3'OH and block intasome activity. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.018

文献信息

• HIV INTEGRASE INHIBITORS
  申请人：Naidu B. Narasimhulu

  公开号：US20070129379A1

  公开（公告）日：2007-06-07

  The invention encompasses a series bicyclic pyrimidinone compounds of Formula I which inhibit HIV integrase and prevent viral integration into human DNA. This action makes the compounds useful for treating HIV infection and AIDS. The invention also encompasses pharmaceutical compositions and methods for treating those infected with HIV.

  这项发明涵盖了一系列公式I的双环嘧啶酮化合物，这些化合物抑制HIV整合酶并防止病毒整合到人类DNA中。这种作用使得这些化合物对治疗HIV感染和艾滋病有用。该发明还涵盖了用于治疗HIV感染者的药物组合物和方法。
• [EN] PYRIMIDINE DERIVATIVES AS HIV INTEGRASE INHIBITORS<br/>[FR] DERIVES DE LA PYRIMIDINE, INHIBITEURS DE L'INTEGRASE DU VIH
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2007064619A1

  公开（公告）日：2007-06-07

  [EN] The invention encompasses a series bicyclic pyrimidinone compounds of Formula I which inhibit HIV integrase and prevent viral integration into human DNA. This action makes the compounds useful for treating HIV infection and AIDS. The invention also encompasses pharmaceutical compositions and methods for treating those infected with HIV. Formula (I)
  [FR] L'invention porte sur une série de composés bicycliques de pyrimidinone de formule (I) qui inhibent l'intégrase du VIH et empêchent l'intégration du virus à l'ADN humain. Cette action rend ces composés utiles pour traiter les infections par le VIH et le SIDA. L'invention porte également sur des préparations pharmaceutiques et des méthodes de traitement des patients infectés par le VIH.
• Design and synthesis of novel pyrimidone analogues as HIV-1 integrase inhibitors
  作者：Shenghui Yu、Tino Wilson Sanchez、Yang Liu、Yanzhen Yin、Nouri Neamati、Guisen Zhao

  DOI：10.1016/j.bmcl.2013.09.018

  日期：2013.11

  A series of novel pyrimidone analogues have been designed and synthesized as HIV-1 integrase (IN) inhibitors. This study demonstrated that introducing a substituent in the N1-position of the pyrimidone scaffold does not significantly influence IN inhibitory activity. Molecular docking studies showed these compounds could occupy the IN active site and form pi-pi interactions with viral DNA nucleotides DC16 and DA17 to displace reactive viral DNA 3'OH and block intasome activity. (c) 2013 Elsevier Ltd. All rights reserved.