4-(3,5-dimethylphenylsulfanyl)-3-iodo-6-methyl-5-(3-phenyl-[1,2,4]triazol-4-ylmethyl)pyridin-2(1H)-one | 1185190-97-9

• 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)-3-iodo-6-methyl-5-(3-phenyl-[1,2,4]triazol-4-ylmethyl)pyridin-2(1H)-one
• 英文别名: 4-(3,5-dimethylphenyl)sulfanyl-3-iodo-6-methyl-5-[(3-phenyl-1,2,4-triazol-4-yl)methyl]-1H-pyridin-2-one
• CAS: 1185190-97-9
• 化学式: C₂₃H₂₁IN₄OS
• 分子量: 528.416
• InChiKey: URTUTWWCVZFORQ-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：
  0.17
• 拓扑面积：
  85.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-苯基-1H-1,2,4-噻唑 、 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 1.5h， 以60 mg的产率得到4-(3,5-dimethylphenylsulfanyl)-3-iodo-6-methyl-5-(3-phenyl-[1,2,4]triazol-4-ylmethyl)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

文献信息

• Synthesis and Biological Evaluation of C-5 Methyl Substituted 4-Arylthio and 4-Aryloxy-3-Iodopyridin-2(1<i>H</i>)-one Type Anti-HIV Agents
  作者：Jérôme Guillemont、Abdellah Benjahad、Said Oumouch、Laurence Decrane、Patrice Palandjian、Daniel Vernier、Laurence Queguiner、Koen Andries、Marie-Pierre de Béthune、Kurt Hertogs、David S. Grierson、Chi Hung Nguyen

  DOI：10.1021/jm900802y

  日期：2009.12.10

  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.