2-(4-trifluoromethylphenyl)-4(5)-phenylimidazole

• 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-trifluoromethylphenyl)-4(5)-phenylimidazole
• 英文别名: 4(5)-phenyl-2-[(4-trifluoromethyl)phenyl]-1H-imidazole；4-phenyl-2-(4-(trifluoromethyl)phenyl)-1H-imidazole；5-phenyl-2-[4-(trifluoromethyl)phenyl]-1H-imidazole
• 化学式: C₁₆H₁₁F₃N₂
• 分子量: 288.272
• InChiKey: AYCBAFIFGGURIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-trifluoromethylphenyl)-4(5)-phenylimidazole 在 盐酸 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 2-(4-trifluoromethylphenyl)-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-(三氟甲基)苄胺肟 、 苯乙炔 在 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以65%的产率得到2-(4-trifluoromethylphenyl)-4(5)-phenylimidazole
  参考文献：
  名称：

  碱促环胺肟与炔烃：简单获得 2,4-二取代咪唑

  摘要：

  已开发出通过 Cs2CO3 促进的酰胺肟与 DMSO 中末端炔烃的环化有效构建咪唑环。该协议为在无过渡金属和无配体的条件下以良好的收率合成 2,4-二取代咪唑提供了一种简单的合成路线, 具有高原子利用率。内部炔烃也可以进行环化，得到 2,4,5-三取代的咪唑。

  DOI：

  10.3390/molecules25163621

文献信息

• 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。
• 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.
• Base-Promoted Annulation of Amidoximes with Alkynes: Simple Access to 2,4-Disubstituted Imidazoles
  作者：Hina Mehmood、Muhammad Asif Iqbal、Le Lu、Ruimao Hua

  DOI：10.3390/molecules25163621

  日期：——

  of imidazole ring by a Cs2CO3-promoted annulation of amidoximes with terminal alkynes in DMSO has been developed. This protocol provides a simple synthetic route with high atom-utilization for the synthesis of 2,4-disubstituted imidazoles in good yields under transition-metal-free and ligand-free conditions. Internal alkynes can also undergo the annulation to give 2,4,5-trisubstituted imidazoles.

  已开发出通过 Cs2CO3 促进的酰胺肟与 DMSO 中末端炔烃的环化有效构建咪唑环。该协议为在无过渡金属和无配体的条件下以良好的收率合成 2,4-二取代咪唑提供了一种简单的合成路线, 具有高原子利用率。内部炔烃也可以进行环化，得到 2,4,5-三取代的咪唑。
• Anticonvulsant activity of 2,4(1H)-diarylimidazoles in mice and rats acute seizure models
  作者：Valentina Zuliani、Marco Fantini、Aradhya Nigam、James P. Stables、Manoj K. Patel、Mirko Rivara

  DOI：10.1016/j.bmc.2010.09.029

  日期：2010.11.15

  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.