5-chloromethyl-3-iodo-6-methyl-4-(3,5-dimethylphenylsulfanyl)pyridin-2(1H)-one | 1185188-76-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-chloromethyl-3-iodo-6-methyl-4-(3,5-dimethylphenylsulfanyl)pyridin-2(1H)-one
• 英文别名: 5-(chloromethyl)-4-(3,5-dimethylphenyl)sulfanyl-3-iodo-6-methyl-1H-pyridin-2-one
• CAS: 1185188-76-4
• 化学式: C₁₅H₁₅ClINOS
• 分子量: 419.714
• InChiKey: SHIPETBTUUUCDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloromethyl-3-iodo-6-methyl-4-(3,5-dimethylphenylsulfanyl)pyridin-2(1H)-one 、 异丙硫醇 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 4-(3,5-dimethylphenylsulfanyl)-3-iodo-5-isopropylthiomethyl-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
• 作为产物：
  描述：

  5-hydroxymethyl-3-iodo-6-methyl-4-(3,5-dimethylphenylsulfanyl)pyridin-2(1H)-one 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 5-chloromethyl-3-iodo-6-methyl-4-(3,5-dimethylphenylsulfanyl)pyridin-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