4-methyl-1-(2-nitrophenyl)-1H-imidazole | 924709-37-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-methyl-1-(2-nitrophenyl)-1H-imidazole
• 英文别名: 4-Methyl-1-(2-nitrophenyl)imidazole
• CAS: 924709-37-5
• 化学式: C₁₀H₉N₃O₂
• 分子量: 203.2
• InChiKey: QZVNULAPUFTIIR-UHFFFAOYSA-N

物化性质

• 沸点：
  386.7±25.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-1-(2-nitrophenyl)-1H-imidazole 在 T406石油添加剂 、 palladium 10% on activated carbon 、 氢气 、 对甲苯磺酸 作用下， 以 乙醇 、 甲苯 为溶剂， 20.0~25.0 ℃ 、310.27 kPa 条件下， 生成 3-methyl-4-(4-nitrophenyl)imidazo[1,5-a]quinoxaline
  参考文献：
  名称：

  Selective synthesis of 4,5-dihydroimidazo- and imidazo[1,5-a]quinoxalines via modified Pictet–Spengler reaction

  摘要：

  An efficient tandem approach for the selective synthesis of 4,5-dihydroimidazo[1,5-a]quinoxalines 6a-g and imidazo[1,5-a]quinoxalines 7a-h by the reaction of 2-imidazolyl anilines 4a-c with aryl aldehydes 5a-k under mild reaction conditions is described. Introduction of electron releasing alkyl groups in substrates 4a-b was found to be instrumental for the success of the reaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.052
• 作为产物：
  描述：

  4-甲基咪唑 、 2-硝基碘苯 在 copper(l) iodide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以52%的产率得到4-methyl-1-(2-nitrophenyl)-1H-imidazole
  参考文献：
  名称：

  Fragment-Based Discovery of a Qualified Hit Targeting the Latency-Associated Nuclear Antigen of the Oncogenic Kaposi’s Sarcoma-Associated Herpesvirus/Human Herpesvirus 8

  摘要：

  The latency-associated nuclear antigen (LANA) is required for latent replication and persistence of Kaposi's sarcoma-associated herpesvirus/human herpesvirus 8. It acts via replicating and tethering the virus episome to the host chromatin and exerts other functions. We conceived a new approach for the discovery of antiviral drugs to inhibit the interaction between LANA and the viral genome. We applied a biophysical screening cascade and identified the first LANA binders from small, structurally diverse compound libraries. Starting from a fragment-sized scaffold, we generated optimized hits via fragment growing using a dedicated fluorescence-polarization-based assay as the structure activity-relationship driver. We improved compound potency to the double-digit micromolar range. Importantly, we qualified the resulting hit through orthogonal methods employing EMSA, STD-NMR, and MST methodologies. This optimized hit provides an ideal starting point for subsequent hit-to-lead campaigns providing evident target-binding, suitable ligand efficiencies, and favorable physicochemical properties.

  DOI：

  10.1021/acs.jmedchem.8b01827

文献信息

• Lewis Acid-Catalyzed Selective Synthesis of Diversely Substituted Indolo- and Pyrrolo[1,2-a]quinoxalines and Quinoxalinones by Modified Pictet-Spengler Reaction
  作者：Akhilesh K. Verma、Rajeev R. Jha、V. Kasi Sankar、Trapti Aggarwal、Rajendra P. Singh、Ramesh Chandra

  DOI：10.1002/ejoc.201101013

  日期：2011.12

  An efficient tandem process for the selective synthesis of 1,2-annulated α-fused quinoxalines using benzotriazole methodology by a modified Pictet–Spengler reaction is described. The approach involves the reaction of arylamines 4 with aromatic aldehydes 5 to furnish 6-endo-dig-cyclized products. Dihydroquinoxalines 6 were selectively obtained by using AlCl3 in tetrahydrofuran (THF) at room temperature

  描述了使用苯并三唑方法通过改进的 Pictet-Spengler 反应选择性合成 1,2-环化 α-稠合喹喔啉的有效串联工艺。该方法涉及芳胺 4 与芳香醛 5 的反应，以提供 6-endo-dig-环化产物。通过在室温下在四氢呋喃 (THF) 中使用 AlCl3 两小时，选择性地获得二氢喹喔啉 6。然而，10 小时后，喹喔啉 7 仅以极好的收率获得。还合成了一系列生物学上重要的氟和哌嗪基取代的喹喔啉。这种开发的方法还提供了一种新型串联合成喹喔啉酮 9 的途径。
• Novel compounds possessing potent cAMP and cGMP phosphodiesterase inhibitory activity. Synthesis and cardiovascular effects of a series of imidazo[1,2-a]quinoxalinones and imidazo[1,5-a]quinoxalinones and their aza analogs
  作者：David D. Davey、P. W. Erhardt、E. H. Cantor、S. S. Greenberg、W. R. Ingebretsen、J. Wiggins

  DOI：10.1021/jm00113a002

  日期：1991.9

  A series of novel imidazoquinoxalinones and their aza analogues were prepared by the cyclization of o-amino(H-1-imidazol-1-yl)aryls and heteroaryls with carbonyldiimidazole. The compounds were screened for inhibition of Type I and Type IV phosphodiesterases (PDE's) and evaluated for their vasorelaxant and positive inotropic activities in vitro. In general, compounds having potent PDE inhibitory activity also possessed good inotropic and vasodilator activity, although linear correlations between these activities could not be established.