N-(7-(cyclohexyl(methyl)amino)-3-oxo-3,4-dihydroquinoxalin-6-ylcarbamothioyl)benzamide | 1325215-81-3

• 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: N-(7-(cyclohexyl(methyl)amino)-3-oxo-3,4-dihydroquinoxalin-6-ylcarbamothioyl)benzamide
• 英文别名: N-[[7-[Cyclohexyl(methyl)amino]-3-oxo-4H-quinoxalin-6-yl]carbamothioyl]benzamide
• CAS: 1325215-81-3
• 化学式: C₂₃H₂₅N₅O₂S
• 分子量: 435.55
• InChiKey: FTWIBUGWDLHHEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(7-(cyclohexyl(methyl)amino)-3-oxo-3,4-dihydroquinoxalin-6-ylcarbamothioyl)benzamide 在 水 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.0h， 生成 4-(2-(7-(cyclohexyl(methyl)amino)-3-oxo-3,4-dihydroquinoxalin-6-ylamino)thiazol-4-yl)benzonitrile
  参考文献：
  名称：

  Quinoxalin-2(1H)-One Derivatives As Inhibitors Against Hepatitis C Virus

  摘要：

  Hepatitis C virus (HCV) infection is a serious problem worldwide, but no effective drugs are currently available. Through screening of our privileged structure library, quinoxalin-2(1H)-one derivative N-(7-(cyclohexyl(methyl)amino)-3-oxo-3,4-dihydroquinoxalin-6-ylcarbamothioyl)benzamide (compound 1) was identified as potent HCV inhibitor in vitro. Subsequently, a structure-activity relationship analysis was carried out that showed N-(7-(cyclohexyl(methyl)amino)-3-oxo-3,4-dihydroquinoxalin-6-ylcarbamothioyl)-furan-2-carboxamide (compound 11, EC(50) = 1.8 mu M, SI = 9.6), 6-(cyclohexyl-(methyl)amino)-7-(4-phenylthiazol-2-ylamino)quinoxalin-2(1H)-one (compound 33, EC(50) = 1.67 mu M, SI = 37.4), 2-(cyclohexyl(methyl)amino)-3-(4-phenylthiazol-2-ylamino)-7,8,9,10-tetrahydro-5H-pyrido[1,2-a]quinoxalin-6(6aH)-one (compound 60, EC(50) = 1.19 mu M, SI = 9.27), 8-(cyclohexyl(methyl)amino)-7-(4-phenylthiazol-2-ylamino)pyrrolo[1,2-a] quinoxalin-4(5H)-one (compound 65, EC(50) = 1.82 mu m, SI = 9.9), and 6-(diethylamino)-7-(4-phenylthiazol-2-ylamino)quinoxalin-2(1H)-one (compound 78, EC(50) = 1.27 mu M, SI = 17.9) acted against HCV. The data from the structure activity relationship study suggests that quinoxalin-2(1H)-one derivatives exhibited potent activity against HCV.

  DOI：

  10.1021/jm200394x
• 作为产物：
  描述：

  methyl 2-(5-fluoro-2,4-dinitrophenylamino)acetate 在 palladium 10% on activated carbon 、 甲酸铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 反应 15.0h， 生成 N-(7-(cyclohexyl(methyl)amino)-3-oxo-3,4-dihydroquinoxalin-6-ylcarbamothioyl)benzamide
  参考文献：
  名称：

  Quinoxalin-2(1H)-One Derivatives As Inhibitors Against Hepatitis C Virus

  摘要：

  Hepatitis C virus (HCV) infection is a serious problem worldwide, but no effective drugs are currently available. Through screening of our privileged structure library, quinoxalin-2(1H)-one derivative N-(7-(cyclohexyl(methyl)amino)-3-oxo-3,4-dihydroquinoxalin-6-ylcarbamothioyl)benzamide (compound 1) was identified as potent HCV inhibitor in vitro. Subsequently, a structure-activity relationship analysis was carried out that showed N-(7-(cyclohexyl(methyl)amino)-3-oxo-3,4-dihydroquinoxalin-6-ylcarbamothioyl)-furan-2-carboxamide (compound 11, EC(50) = 1.8 mu M, SI = 9.6), 6-(cyclohexyl-(methyl)amino)-7-(4-phenylthiazol-2-ylamino)quinoxalin-2(1H)-one (compound 33, EC(50) = 1.67 mu M, SI = 37.4), 2-(cyclohexyl(methyl)amino)-3-(4-phenylthiazol-2-ylamino)-7,8,9,10-tetrahydro-5H-pyrido[1,2-a]quinoxalin-6(6aH)-one (compound 60, EC(50) = 1.19 mu M, SI = 9.27), 8-(cyclohexyl(methyl)amino)-7-(4-phenylthiazol-2-ylamino)pyrrolo[1,2-a] quinoxalin-4(5H)-one (compound 65, EC(50) = 1.82 mu m, SI = 9.9), and 6-(diethylamino)-7-(4-phenylthiazol-2-ylamino)quinoxalin-2(1H)-one (compound 78, EC(50) = 1.27 mu M, SI = 17.9) acted against HCV. The data from the structure activity relationship study suggests that quinoxalin-2(1H)-one derivatives exhibited potent activity against HCV.

  DOI：

  10.1021/jm200394x

文献信息

• Quinoxalin-2(1<i>H</i>)-One Derivatives As Inhibitors Against Hepatitis C Virus
  作者：Rui Liu、Zhuhui Huang、Michael G. Murray、Xiaoyong Guo、Gang Liu

  DOI：10.1021/jm200394x

  日期：2011.8.25

  Hepatitis C virus (HCV) infection is a serious problem worldwide, but no effective drugs are currently available. Through screening of our privileged structure library, quinoxalin-2(1H)-one derivative N-(7-(cyclohexyl(methyl)amino)-3-oxo-3,4-dihydroquinoxalin-6-ylcarbamothioyl)benzamide (compound 1) was identified as potent HCV inhibitor in vitro. Subsequently, a structure-activity relationship analysis was carried out that showed N-(7-(cyclohexyl(methyl)amino)-3-oxo-3,4-dihydroquinoxalin-6-ylcarbamothioyl)-furan-2-carboxamide (compound 11, EC(50) = 1.8 mu M, SI = 9.6), 6-(cyclohexyl-(methyl)amino)-7-(4-phenylthiazol-2-ylamino)quinoxalin-2(1H)-one (compound 33, EC(50) = 1.67 mu M, SI = 37.4), 2-(cyclohexyl(methyl)amino)-3-(4-phenylthiazol-2-ylamino)-7,8,9,10-tetrahydro-5H-pyrido[1,2-a]quinoxalin-6(6aH)-one (compound 60, EC(50) = 1.19 mu M, SI = 9.27), 8-(cyclohexyl(methyl)amino)-7-(4-phenylthiazol-2-ylamino)pyrrolo[1,2-a] quinoxalin-4(5H)-one (compound 65, EC(50) = 1.82 mu m, SI = 9.9), and 6-(diethylamino)-7-(4-phenylthiazol-2-ylamino)quinoxalin-2(1H)-one (compound 78, EC(50) = 1.27 mu M, SI = 17.9) acted against HCV. The data from the structure activity relationship study suggests that quinoxalin-2(1H)-one derivatives exhibited potent activity against HCV.