5,10-dioxo-N¹,N⁶-di-p-tolyl-5,10-dihydrodiimidazo[1,5-a:1',5'-d]pyrazine-1,6-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: 5,10-dioxo-N¹,N⁶-di-p-tolyl-5,10-dihydrodiimidazo[1,5-a:1',5'-d]pyrazine-1,6-dicarboxamide
• 英文别名: N,N'-di-4-methylphenyl-5,10-dioxo-5H,10H-diimidazo[1,5-a:1',5'-d]pyrazine-1,6-dicarboxamide；4-N,10-N-bis(4-methylphenyl)-2,8-dioxo-1,5,7,11-tetrazatricyclo[7.3.0.03,7]dodeca-3,5,9,11-tetraene-4,10-dicarboxamide
• 化学式: C₂₄H₁₈N₆O₄
• 分子量: 454.445
• InChiKey: AYZNEKOCJFYFGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,10-dioxo-N¹,N⁶-di-p-tolyl-5,10-dihydrodiimidazo[1,5-a:1',5'-d]pyrazine-1,6-dicarboxamide 、 肼 以75%的产率得到
  参考文献：
  名称：

  IVANOV, EH. I.;BOGATSKIJ, A. V.;IVANOVA, R. YU., YKP. XIM. ZH., 1983, 49, N 12, 1301-1306

  摘要：

  DOI：
• 作为产物：
  描述：

  咪唑-4,5-二羧酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 、 N,N-二乙基苯胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 16.0h， 生成 5,10-dioxo-N¹,N⁶-di-p-tolyl-5,10-dihydrodiimidazo[1,5-a:1',5'-d]pyrazine-1,6-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

• Imidazole-4,5-dicarboxamide Derivatives with Antiproliferative Activity against HL-60 Cells
  作者：Elisabeth M. Perchellet、Jean-Pierre Perchellet、Paul W. Baures

  DOI：10.1021/jm050160r

  日期：2005.9.1

  5-dicarboxamides (I45DCs) were prepared and tested in order to determine their antiproliferative activity against HL-60 cells. The design of the I45DCs was based in part on the structures of trisubstituted purines complexed with cyclin dependent kinase 2 (cdk2), a protein important in regulating the G1/S transition in the cell cycle, and the intramolecular hydrogen bond in I45DCs that predisposes the conformation

  制备并测试了一系列N，N'-二取代的咪唑-4,5-二甲酰胺（I45DCs），以确定它们对HL-60细胞的抗增殖活性。I45DC的设计部分基于与细胞周期蛋白依赖性激酶2（cdk2）复合的三取代嘌呤的结构，一种在细胞周期中调节G1 / S过渡的重要蛋白质以及I45DCs中的分子内氢键模仿取代的腺苷的构象。通过MTS线粒体功能测定法测定的IC50在2.5-25 microM范围内，本研究中的大多数I45DC抑制HL-60细胞的增殖。I45DC的SAR与cdk2的ATP结合位点中预期的氢键相互作用一致。因此，
• 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.
• IVANOV, EH. I.;BOGATSKIJ, A. V.;IVANOVA, R. YU., YKP. XIM. ZH., 1983, 49, N 12, 1301-1306
  作者：IVANOV, EH. I.、BOGATSKIJ, A. V.、IVANOVA, R. YU.

  DOI：——

  日期：——