2-(4-nitrophenyl)-4(5)-phenylimidazole | 36783-89-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-nitrophenyl)-4(5)-phenylimidazole
• 英文别名: 4(5)-phenyl-2-(4-nitrophenyl)-1H-imidazole；2-(4-nitrophenyl)-4-phenyl-1H-imidazole；2-(4-nitrophenyl)-5-phenyl-1H-imidazole
• CAS: 36783-89-8
• 化学式: C₁₅H₁₁N₃O₂
• 分子量: 265.271
• InChiKey: NVMIEUCZOPTAMD-UHFFFAOYSA-N

物化性质

• 熔点：
  172-173 °C
• 沸点：
  541.5±33.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-nitrophenyl)-4(5)-phenylimidazole 在 盐酸 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 2-(4-nitrophenyl)-4(5)-phenylimidazole hydrochloride
  参考文献：
  名称：

  Anticonvulsant activity of 2,4(1H)-diarylimidazoles in mice and rats acute seizure models

  摘要：

  2,4(1H)-Diarylimidazoles have been previously shown to inhibit hNaV1.2 sodium (Na) channel currents. Since many of the clinically used anticonvulsants are known to inhibit Na channels as an important mechanism of their action, these compounds were tested in two acute rodent seizure models for anticonvulsant activity (MES and scMet) and for sedative and ataxic side effects. Compounds exhibiting antiepileptic activity were further tested to establish a dose response curve (ED(50)). The experimental data identified four compounds with anticonvulsant activity in the MES acute seizure rodent model (compound 10, ED(50) = 61.7 mg/kg; compound 13, ED(50) = 46.8 mg/kg, compound 17, ED(50) = 129.5 mg/kg and compound 20, ED(50) = 136.7 mg/kg). Protective indexes (PI = TD(50)/ED(50)) ranged from 2.1 (compound 10) to greater than 3.6 (compounds 13, 17 and 20). All four compounds were shown to inhibit hNaV1.2 in a dose dependant manner. Even if a correlation between sodium channel inhibition and anticonvulsant activity was unclear, these studies identify four Na channel antagonists with anticonvulsant activity, providing evidence that these derivatives could be potential drug candidates for development as safe, new and effective antiepileptic drugs (AEDs). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.029
• 作为产物：
  描述：

  4-硝基苯甲酰氯 在 吡啶 、 dibromobis(triphenylphosphine)nickel(II) 、 sodium sulfate 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 甲苯 为溶剂， 反应 36.0h， 生成 2-(4-nitrophenyl)-4(5)-phenylimidazole
  参考文献：
  名称：

  通过C-C偶联和C-N缩合级联反应进行镍催化的2,4-二取代的咪唑的构建

  摘要：

  开发了一种方便的Ni（II）催化的C-C和C-N级联偶联反应，可直接使用各种2,4-二取代的咪唑。反应范围涵盖了各种芳基和脂肪族取代基，显示出中等至优异的收率。卤素和公差Ñ含杂环基团的演示此方法作进一步的合成探索的多功能性。

  DOI：

  10.1002/adsc.201900096

文献信息

• Modular Synthesis of Di- and Trisubstituted Imidazoles from Ketones and Aldehydes: A Route to Kinase Inhibitors
  作者：Ian de Toledo、Thiago A. Grigolo、James M. Bennett、Jonathan M. Elkins、Ronaldo A. Pilli

  DOI：10.1021/acs.joc.9b01844

  日期：2019.11.1

  A one-pot and modular approach to the synthesis of 2,4(5)-disubstituted imidazoles was developed based on ketone oxidation, employing catalytic HBr and DMSO, followed by imidazole condensation with aldehydes. This methodology afforded twenty-nine disubstituted NH-imidazoles (23%-85% yield). A three-step synthesis of 20 kinase inhibitors was achieved by employing this oxidation-condensation protocol

  基于酮氧化，采用催化HBr和DMSO，然后通过咪唑与醛的缩合反应，开发了一种单罐模块化方法，用于合成2,4（5）-二取代的咪唑。该方法提供了二十九个二取代的NH-咪唑（23％-85％的产率）。通过采用这种氧化-缩合方案，然后在咪唑环中进行溴化和Suzuki偶联，得到三取代的NH-咪唑（23％-69％，三步法），实现了三步合成20种激酶抑制剂的过程。该方法还用于合成已知抑制剂GSK3037619A。
• Efficient and Practical Synthesis of 4(5)-Aryl-1<i>H</i>-imidazoles and 2,4(5)-Diaryl-1<i>H</i>-imidazoles via Highly Selective Palladium-Catalyzed Arylation Reactions
  作者：Fabio Bellina、Silvia Cauteruccio、Renzo Rossi

  DOI：10.1021/jo701496p

  日期：2007.10.1

  be efficiently and selectively prepared by PdCl2(dppf)-catalyzed Suzuki−Miyaura reaction of commercially available 4(5)-bromo-1H-imidazole with arylboronic acids under phase-transfer conditions. On the other hand, N-unprotected 4(5)-aryl-1H-imidazoles can undergo highly selective Pd(OAc)2-catalyzed and CuI-mediated direct C-2-arylation with a variety of aryl bromides and iodides under base-free and

  通过PdCl 2（dppf）催化的Suzuki-Miyaura反应可在相转移条件下对市售4（5）-bromo-1 H-咪唑与芳基硼酸进行反应，可有效地选择性制备4（5）-Aryl-1 H-咪唑条件。另一方面，N-未保护的4（5）-芳基-1 H-咪唑可在碱下与多种芳基溴化物和碘化物进行高选择性Pd（OAc）2催化和CuI介导的直接C-2-芳基化无和无配体的条件下，以适度到良好的产率生产2,4（5）-二芳基-1 H-咪唑。在用于制备2,4（5）-二芳基-1 H-咪唑的实验条件下未观察到N-芳基化副产物。
• Husain, Asif; Drabu, Sushma; Kumar, Nitin, Acta poloniae pharmaceutica, 2009, vol. 66, # 3, p. 243 - 248
  作者：Husain, Asif、Drabu, Sushma、Kumar, Nitin

  DOI：——

  日期：——
• Dye-sensitized Photooxidation of 2,4-Disubstituted Imidazoles: The Formation of Isomeric Imidazolinones
  作者：Mikio Suzuki、Shigeo Kai

  DOI：10.3987/com-96-7452

  日期：——
• A Practical Synthesis of 2,4(5)-Diarylimidazoles from Simple Building Blocks
  作者：Valentina Zuliani、Giuseppe Cocconcelli、Marco Fantini、Chiara Ghiron、Mirko Rivara

  DOI：10.1021/jo070187d

  日期：2007.6.1

  A simple and efficient approach to selectively obtain 2,4(5)-diarylimidazoles suppressing formation of 2-aroyl-4(5)-arylimidazoles is described. The yield of each of the two products strongly depends on the reaction conditions employed. This reaction provides a simple method to prepare small libraries of biologically active compounds by parallel synthesis.