2-(4(5)-phenylimidazol-2-yl)benzofuran | 1086462-15-8

• 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(5)-phenylimidazol-2-yl)benzofuran
• 英文别名: 2-(1-benzofuran-2-yl)-5-phenyl-1H-imidazole
• CAS: 1086462-15-8
• 化学式: C₁₇H₁₂N₂O
• 分子量: 260.295
• InChiKey: UWKHQZKCGYBCHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯基丙醇水合物 、 苯并[b]呋喃-2-甲醛 在 ammonium acetate 作用下， 以 甲醇 为溶剂， 生成 2-(4(5)-phenylimidazol-2-yl)benzofuran
  参考文献：
  名称：

  2,4（5）-Diarylimidazoles：对抗hNa（v）1.2的新型钠通道阻滞剂的合成和生物学评估。

  摘要：

  通过简单有效的合成方法制备了少量的新型2,4（5）-二芳基咪唑，并将其评估为hNa（v）1.2钠通道电流的潜在抑制剂。该系列的一个成员（4）表现出对Na（v）1.2电流的强烈抑制作用，作为一种有前途的先导化合物，可用于进一步的结构-活性关系研究，以开发新型钠通道阻滞剂。

  DOI：

  10.1016/j.bmcl.2008.09.036

文献信息

• 2,4(5)-Diarylimidazoles: Synthesis and biological evaluation of a new class of sodium channel blockers against hNav1.2
  作者：Mirko Rivara、Aparna R. Baheti、Marco Fantini、Giuseppe Cocconcelli、Chiara Ghiron、Christopher L. Kalmar、Natasha Singh、Ellen C. Merrick、Manoj K. Patel、Valentina Zuliani

  DOI：10.1016/j.bmcl.2008.09.036

  日期：2008.10

  4(5)-diarylimidazoles were prepared through a simple and efficient synthesis and evaluated as potential inhibitors of hNa(v)1.2 sodium channel currents. One member of this series (4) exhibited profound inhibition of Na(v)1.2 currents, emerging as a promising lead compound for further structure-activity relationship studies for the development of novel sodium channel blockers.

  通过简单有效的合成方法制备了少量的新型2,4（5）-二芳基咪唑，并将其评估为hNa（v）1.2钠通道电流的潜在抑制剂。该系列的一个成员（4）表现出对Na（v）1.2电流的强烈抑制作用，作为一种有前途的先导化合物，可用于进一步的结构-活性关系研究，以开发新型钠通道阻滞剂。
• 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.