7-amino-6-(cyclohexyl(methyl)amino)quinoxalin-2(1H)-one | 1325215-84-6

• 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: 7-amino-6-(cyclohexyl(methyl)amino)quinoxalin-2(1H)-one
• 英文别名: 7-amino-6-[cyclohexyl(methyl)amino]-1H-quinoxalin-2-one
• CAS: 1325215-84-6
• 化学式: C₁₅H₂₀N₄O
• 分子量: 272.35
• InChiKey: LNVJTDQHQVCHOZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-amino-6-(cyclohexyl(methyl)amino)quinoxalin-2(1H)-one 在 吡啶 、 水 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 丙酮 为溶剂， 反应 10.0h， 生成 1-(7-(cyclohexyl(methyl)amino)-3-oxo-3,4-dihydroquinoxalin-6-yl)-3-(4-fluorobenzyl)guanidine
  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 为溶剂， 反应 11.0h， 生成 7-amino-6-(cyclohexyl(methyl)amino)quinoxalin-2(1H)-one
  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

• Silver‐Enabled General Radical Difluoromethylation Reaction with TMSCF ₂ H
  作者：Jun Yang、Shengqing Zhu、Fang Wang、Feng‐Ling Qing、Lingling Chu

  DOI：10.1002/anie.202014587

  日期：2021.2.19

  A silver‐mediated oxidative difluoromethylation of styrenes and vinyl trifluoroborates with TMSCF2H is reported for the first time. This method enables direct and facile access to CF2H‐alkenes from abundant alkenes with excellent functional‐group compatibility. Moreover, this Ag/TMSCF2H protocol could further enable a series of radical difluoromethylation reactions of a wide array of substrates, offering

  首次报道了用TMSCF 2 H对苯乙烯和三氟硼酸乙烯基酯进行银介导的氧化二氟甲基化。这种方法可以从丰富的烯烃中直接和轻松地获得CF 2 H-烯烃，并且具有出色的官能团相容性。此外，该Ag / TMSCF 2 H方案可以进一步实现一系列底物的一系列自由基二氟甲基化反应，从而为构建多样化的C-CF 2 H键提供通用和互补的平台。
• 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.