{1-[4-(3,5-dimethylphenylsulfanyl)-5-iodo-2-methyl-6-oxo-1,6-dihydropyridin-3-ylmethyl]-5-methyl-1H-[1,2,4]triazol-3-yl}acetonitrile | 1185190-42-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: {1-[4-(3,5-dimethylphenylsulfanyl)-5-iodo-2-methyl-6-oxo-1,6-dihydropyridin-3-ylmethyl]-5-methyl-1H-[1,2,4]triazol-3-yl}acetonitrile
• 英文别名: 2-[1-[[4-(3,5-dimethylphenyl)sulfanyl-5-iodo-2-methyl-6-oxo-1H-pyridin-3-yl]methyl]-5-methyl-1,2,4-triazol-3-yl]acetonitrile
• CAS: 1185190-42-4
• 化学式: C₂₀H₂₀IN₅OS
• 分子量: 505.382
• InChiKey: NYMWMCISZHGGRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-chloromethyl-3-iodo-6-methyl-4-(3,5-dimethylphenylsulfanyl)pyridin-2(1H)-one 、 2-(5-甲基-4H-1,2,4-噻唑-3-基)乙腈 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以62 mg的产率得到{1-[4-(3,5-dimethylphenylsulfanyl)-5-iodo-2-methyl-6-oxo-1,6-dihydropyridin-3-ylmethyl]-5-methyl-1H-[1,2,4]triazol-3-yl}acetonitrile
  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