N⁵-(4-fluorophenyl)-N⁴-(4-methyl-2-(thiophen-3-yl)phenyl)-1H-imidazole-4,5-dicarboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N⁵-(4-fluorophenyl)-N⁴-(4-methyl-2-(thiophen-3-yl)phenyl)-1H-imidazole-4,5-dicarboxamide
• 英文别名: 4-N-(4-fluorophenyl)-5-N-(4-methyl-2-thiophen-3-ylphenyl)-1H-imidazole-4,5-dicarboxamide
• 化学式: C₂₂H₁₇FN₄O₂S
• 分子量: 420.467
• InChiKey: AUKIURKRHKWAMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-溴-4-甲基苯胺 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.5h， 生成 N⁵-(4-fluorophenyl)-N⁴-(4-methyl-2-(thiophen-3-yl)phenyl)-1H-imidazole-4,5-dicarboxamide
  参考文献：
  名称：

  Synthesis and evaluation of imidazole-4,5- and pyrazine-2,3-dicarboxamides targeting dengue and yellow fever virus

  摘要：

  The results of a high-throughput screening assay using the dengue virus-2 replicon showed that the imidazole 4,5-dicarboxamide (I45DC) derivative (15a) has a high dengue virus inhibitory activity. Based on 15a as a lead compound, a novel class of both disubstituted I45DCs and the resembling pyrazine 2,3-dicarboxamides (P23DC5) were synthesized. Here, we report on their in vitro inhibitory activity against dengue virus (DENV) and yellow fever virus (YFV). Some of these first generation compounds have shown activity against both viruses in the micromolar range. Within this series, compound 15b was observed to display the highest antiviral potency against YFV with an EC50 = 1.85 mu M. In addition, compounds 20a and 20b both potently inhibited replication of DENV (EC50 = 0.93 mu M) in Vero cells. (c) 2014 The Authors. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2014.09.062

文献信息

• Synthesis and evaluation of imidazole-4,5- and pyrazine-2,3-dicarboxamides targeting dengue and yellow fever virus
  作者：Milind Saudi、Joanna Zmurko、Suzanne Kaptein、Jef Rozenski、Johan Neyts、Arthur Van Aerschot

  DOI：10.1016/j.ejmech.2014.09.062

  日期：2014.11

  The results of a high-throughput screening assay using the dengue virus-2 replicon showed that the imidazole 4,5-dicarboxamide (I45DC) derivative (15a) has a high dengue virus inhibitory activity. Based on 15a as a lead compound, a novel class of both disubstituted I45DCs and the resembling pyrazine 2,3-dicarboxamides (P23DC5) were synthesized. Here, we report on their in vitro inhibitory activity against dengue virus (DENV) and yellow fever virus (YFV). Some of these first generation compounds have shown activity against both viruses in the micromolar range. Within this series, compound 15b was observed to display the highest antiviral potency against YFV with an EC50 = 1.85 mu M. In addition, compounds 20a and 20b both potently inhibited replication of DENV (EC50 = 0.93 mu M) in Vero cells. (c) 2014 The Authors. Published by Elsevier Masson SAS.