5-(2-aminomethylmorpholin-4-ylmethyl)-4-(3,5-dimethylphenylsulfanyl)-3-iodo-6-methylpyridin-2(1H)-one | 1185190-91-3

• 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-(2-aminomethylmorpholin-4-ylmethyl)-4-(3,5-dimethylphenylsulfanyl)-3-iodo-6-methylpyridin-2(1H)-one
• 英文别名: 5-[[2-(aminomethyl)morpholin-4-yl]methyl]-4-(3,5-dimethylphenyl)sulfanyl-3-iodo-6-methyl-1H-pyridin-2-one
• CAS: 1185190-91-3
• 化学式: C₂₀H₂₆IN₃O₂S
• 分子量: 499.416
• InChiKey: ZTPFJRIWBSVPCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  92.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 5-(2-aminomethylmorpholin-4-ylmethyl)-4-(3,5-dimethylphenylsulfanyl)-3-iodo-6-methylpyridin-2(1H)-one 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 水 为溶剂， 以116 mg的产率得到5-(2-dimethylaminomethylmorpholin-4-ylmethyl)-4-(3,5-dimethylphenylsulfanyl)-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
• 作为产物：
  描述：

  tert-butyl {4-[4-(3,5-dimethyl-phenylsulfanyl)-5-iodo-2-methyl-6-oxo-1,6-dihydropyridin-3-ylmethyl]-morpholin-2-ylmethyl}-carbamate 在 盐酸 作用下， 以 水 、 异丙醇 为溶剂， 反应 0.5h， 生成 5-(2-aminomethylmorpholin-4-ylmethyl)-4-(3,5-dimethylphenylsulfanyl)-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