1-[4-(3,5-dimethylphenoxy)-5-iodo-2-methyl-6-oxo-1,6-dihydropyridin-3-ylmethyl]-1H-imidazole-4,5-dicarbonitrile | 1185189-56-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[4-(3,5-dimethylphenoxy)-5-iodo-2-methyl-6-oxo-1,6-dihydropyridin-3-ylmethyl]-1H-imidazole-4,5-dicarbonitrile
• 英文别名: 1-[[4-(3,5-dimethylphenoxy)-5-iodo-2-methyl-6-oxo-1H-pyridin-3-yl]methyl]imidazole-4,5-dicarbonitrile
• CAS: 1185189-56-3
• 化学式: C₂₀H₁₆IN₅O₂
• 分子量: 485.284
• InChiKey: REIFVAZPGNUJLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,5-二氰基咪唑 、 5-chloromethyl-3-iodo-6-methyl-4-(3,5-dimethylpheoxy)pyridin-2(1H)-one 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 1-[4-(3,5-dimethylphenoxy)-5-iodo-2-methyl-6-oxo-1,6-dihydropyridin-3-ylmethyl]-1H-imidazole-4,5-dicarbonitrile
  参考文献：
  名称：

  Synthesis and Biological Evaluation of C-5 Methyl Substituted 4-Arylthio and 4-Aryloxy-3-Iodopyridin-2(1H)-one Type Anti-HIV Agents

  摘要：

  A series of C-5 methyl substituted 4-arylthio- and 4-aryloxy-3-iodopyridin-2(1H)-ones hits been synthesized its new pyridinone analogues for their evaluation as anti-HIV inhibitors. The optimization at the 5-position wits developed through an efficient use of the key intermediates 5-ethoxycarbonyl- and 5-cyano-pyridin-2(1H)-ones (14 and 15). Biological studies revealed that several compounds show potent HIV-1 reverse transcriptase inhibitory properties, for example, compounds 93 and 99 are active at 0.6-50 nM against wild type HIV-1 and a panel of major simple/double HIV mutant strains.

  DOI：

  10.1021/jm900802y