4-(3,5-dimethylphenylsulfanyl)-5-(5-furan-2-yl-3-methyl-[1,2,4]triazol-1-ylmethyl)-3-iodo-6-methylpyridin-2(1H)-one | 1185190-93-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(3,5-dimethylphenylsulfanyl)-5-(5-furan-2-yl-3-methyl-[1,2,4]triazol-1-ylmethyl)-3-iodo-6-methylpyridin-2(1H)-one
• 英文别名: 4-(3,5-dimethylphenyl)sulfanyl-5-[[5-(furan-2-yl)-3-methyl-1,2,4-triazol-1-yl]methyl]-3-iodo-6-methyl-1H-pyridin-2-one
• CAS: 1185190-93-5
• 化学式: C₂₂H₂₁IN₄O₂S
• 分子量: 532.405
• InChiKey: JKYQBIAHWAYHOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  98.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-furan-2-yl-3-methyl-1H-[1,2,4]triazole 、 5-chloromethyl-3-iodo-6-methyl-4-(3,5-dimethylphenylsulfanyl)pyridin-2(1H)-one 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以100 mg的产率得到4-(3,5-dimethylphenylsulfanyl)-5-(3-furan-2-yl-5-methyl-[1,2,4]triazol-1-ylmethyl)-3-iodo-6-methylpyridin-2(1H)-one
  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