2-benzyl-3-(cyclohexylmethyl)-3H-imidazo[4,5-g]quinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-benzyl-3-(cyclohexylmethyl)-3H-imidazo[4,5-g]quinoline
• 英文别名: 2-Benzyl-3-(cyclohexylmethyl)imidazo[4,5-g]quinoline；2-benzyl-3-(cyclohexylmethyl)imidazo[4,5-g]quinoline
• 化学式: C₂₄H₂₅N₃
• 分子量: 355.483
• InChiKey: SNAQTJWQFSAWIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环己甲胺 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~100.0 ℃ 、303.99 kPa 条件下， 反应 14.0h， 生成 2-benzyl-3-(cyclohexylmethyl)-3H-imidazo[4,5-g]quinoline
  参考文献：
  名称：

  Synthesis, cytotoxicity and antiviral evaluation of new series of imidazo[4,5-g]quinoline and pyrido[2,3-g]quinoxalinone derivatives

  摘要：

  Linear aromatic N-tricyclic compounds with promising antiviral activity and minimal cytotoxicity were prepared and analyzed in the last years. Specifically, the pyrido[2,3-g]quinoxalinone nucleus was found endowed with high potency against several pathogenic RNA viruses as etiological agents of important veterinary and human pathologies. Following our research program on new antiviral agents we have designed, synthesized and assayed new series of imidazo[4,5-g]quinoline and pyrido[2,3-g]quinoxalinone derivatives. Lead compounds 1-4 were further modified to enhance their antiviral activity and reduce their cytotoxicity. Thus, different substituents were introduced on N atom at position 1 or the 0 atom at position 2 of the leads; contextually, several groups were inserted on the nitrogen atom at position 7 of diaminoquinoline intermediates. Title compounds were tested in cell-based assays for cytotoxicity and antiviral activity against RNA virus families containing single-stranded (either positive-sense (ssRNA+) or negative-sense (ssRNA-)), and double-stranded genomes (dsRNA), and against two representatives of DNA virus families. Some derivatives emerged as potential leads for further development as antiviral agents against some viruses of public health significance, such as RSV, Reo, BVDV and HCV. Particularly, compounds 4, 11b, 11c, 13c, 15a,18 and 21 resulted active against BVDV at concentrations ranging from 1.3 to 5 mu M. Compound 21 was also evaluated for its activity on the BVDV RdRp. Compound 4 was also tested as potential anti-HCV compound in a subgenomic replication assay. Molecular simulation results provided a molecular rationale for the anti-BVDV activity of these compounds. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.002

文献信息

• Synthesis, cytotoxicity and antiviral evaluation of new series of imidazo[4,5-g]quinoline and pyrido[2,3-g]quinoxalinone derivatives
  作者：Irene Briguglio、Roberta Loddo、Erik Laurini、Maurizio Fermeglia、Sandra Piras、Paola Corona、Paolo Giunchedi、Elisabetta Gavini、Giuseppina Sanna、Gabriele Giliberti、Cristina Ibba、Pamela Farci、Paolo La Colla、Sabrina Pricl、Antonio Carta

  DOI：10.1016/j.ejmech.2015.10.002

  日期：2015.11

  Linear aromatic N-tricyclic compounds with promising antiviral activity and minimal cytotoxicity were prepared and analyzed in the last years. Specifically, the pyrido[2,3-g]quinoxalinone nucleus was found endowed with high potency against several pathogenic RNA viruses as etiological agents of important veterinary and human pathologies. Following our research program on new antiviral agents we have designed, synthesized and assayed new series of imidazo[4,5-g]quinoline and pyrido[2,3-g]quinoxalinone derivatives. Lead compounds 1-4 were further modified to enhance their antiviral activity and reduce their cytotoxicity. Thus, different substituents were introduced on N atom at position 1 or the 0 atom at position 2 of the leads; contextually, several groups were inserted on the nitrogen atom at position 7 of diaminoquinoline intermediates. Title compounds were tested in cell-based assays for cytotoxicity and antiviral activity against RNA virus families containing single-stranded (either positive-sense (ssRNA+) or negative-sense (ssRNA-)), and double-stranded genomes (dsRNA), and against two representatives of DNA virus families. Some derivatives emerged as potential leads for further development as antiviral agents against some viruses of public health significance, such as RSV, Reo, BVDV and HCV. Particularly, compounds 4, 11b, 11c, 13c, 15a,18 and 21 resulted active against BVDV at concentrations ranging from 1.3 to 5 mu M. Compound 21 was also evaluated for its activity on the BVDV RdRp. Compound 4 was also tested as potential anti-HCV compound in a subgenomic replication assay. Molecular simulation results provided a molecular rationale for the anti-BVDV activity of these compounds. (C) 2015 Elsevier Masson SAS. All rights reserved.