4-(2,4-bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridine-8-carbonyl)piperazin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-(2,4-bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridine-8-carbonyl)piperazin-2-one
• 英文别名: 4-[2,4-Bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridine-8-carbonyl]piperazin-2-one；4-[2,4-bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridine-8-carbonyl]piperazin-2-one
• 化学式: C₁₇H₁₁F₆N₅O₂
• 分子量: 431.297
• InChiKey: JLQWXTBSDZWCLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  79.6
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  六氟乙酰丙酮 在 硫酸 、 水 、 溶剂黄146 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 lithium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 30.0h， 生成 4-(2,4-bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridine-8-carbonyl)piperazin-2-one
  参考文献：
  名称：

  Discovery of Imidazo[1,2-α][1,8]naphthyridine Derivatives as Potential HCV Entry Inhibitor

  摘要：

  RO8191 represents a newly discovered small-molecule IFN-like agent that displays potent anti-HCV activity. With it as lead, a series of compounds bearing an imidazo[1,2-alpha][1,8]naphthyridine core and an amide bond-linked side chain were designed and synthesized. These compounds were evaluated on HCV cell culture system (HCVcc-hRluc-JFH1), and some of them exhibited remarkable anti-HCV activity (EC50 = 0.017-0.159 mu M) and low toxicity (CC50 > 25 mu M). Moreover, it was revealed that these newly identified anti-HCV agents exert their antiviral effect through a distinct mechanism of action from that of RO8191 by targeting the viral entry process. Thus, our study provides a starting point for the development of potential HCV entry inhibitor.

  DOI：

  10.1021/acsmedchemlett.5b00159

文献信息

• Discovery of Imidazo[1,2-α][1,8]naphthyridine Derivatives as Potential HCV Entry Inhibitor
  作者：Huan Wang、Shuo Wang、Lili Cheng、Ligong Chen、Yongguang Wang、Jie Qing、Shengdian Huang、Yuanhao Wang、Xiaoqiang Lei、Yunfei Wu、Zhilong Ma、Linqi Zhang、Yefeng Tang

  DOI：10.1021/acsmedchemlett.5b00159

  日期：2015.9.10

  RO8191 represents a newly discovered small-molecule IFN-like agent that displays potent anti-HCV activity. With it as lead, a series of compounds bearing an imidazo[1,2-alpha][1,8]naphthyridine core and an amide bond-linked side chain were designed and synthesized. These compounds were evaluated on HCV cell culture system (HCVcc-hRluc-JFH1), and some of them exhibited remarkable anti-HCV activity (EC50 = 0.017-0.159 mu M) and low toxicity (CC50 > 25 mu M). Moreover, it was revealed that these newly identified anti-HCV agents exert their antiviral effect through a distinct mechanism of action from that of RO8191 by targeting the viral entry process. Thus, our study provides a starting point for the development of potential HCV entry inhibitor.