4-(3,5-dimethylphenylsulfanyl)-5-iodo-2-methyl-6-oxo-1,6-dihydropyridin-3-ylcarbonitrile | 1185189-92-7

• 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-iodo-2-methyl-6-oxo-1,6-dihydropyridin-3-ylcarbonitrile
• 英文别名: 4-(3,5-dimethylphenyl)sulfanyl-5-iodo-2-methyl-6-oxo-1H-pyridine-3-carbonitrile
• CAS: 1185189-92-7
• 化学式: C₁₅H₁₃IN₂OS
• 分子量: 396.252
• InChiKey: NXGGBSFHQISKRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3,5-dimethylphenylsulfanyl)-5-iodo-2-methyl-6-oxo-1,6-dihydropyridin-3-ylcarbonitrile 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 以50%的产率得到5-aminomethyl-4-(3,5-dimethylphenylsulfanyl)-3-iodo-6-methyl-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
• 作为产物：
  描述：

  4-(3,5-dimethylphenylsulfanyl)-2-methyl-6-oxo-1,6-dihydropyridin-3-ylcarbonitrile 在 N-碘代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以61%的产率得到4-(3,5-dimethylphenylsulfanyl)-5-iodo-2-methyl-6-oxo-1,6-dihydropyridin-3-ylcarbonitrile
  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.