2-phenyl-4(5)-(3-methoxyphenyl)imidazole

• 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-phenyl-4(5)-(3-methoxyphenyl)imidazole
• 英文别名: 2-phenyl-4-(3'-methoxyphenyl)imidazole；3-methoxy-1-(2-phenylimidazol-4-yl)benzene；4-(3-methoxyphenyl)-2-phenyl-1H-imidazole；5-(3-methoxyphenyl)-2-phenyl-1H-imidazole
• 化学式: C₁₆H₁₄N₂O
• 分子量: 250.3
• InChiKey: WEYUTGFDGHKVAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenyl-4(5)-(3-methoxyphenyl)imidazole 在 盐酸 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 2-phenyl-4(5)-(3-methoxyphenyl)imidazole 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：

  3-甲氧基苯乙酮 在 磺酰氯 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 11.0h， 生成 2-phenyl-4(5)-(3-methoxyphenyl)imidazole
  参考文献：
  名称：

  신규 이미다졸 화합물, 표면 처리제, 프린트 회로 기판 및 그 제조 방법

  摘要：

  (과제) 该发明提供了一种适用于表面处理剂，其具有高溶解度的有机酸溶液，抑制了因处理液的pH变化或蒸发而导致的咪唑类化合物的沉淀，并且可以稳定地继续使用于受到印刷版或软蚀刻处理中杂质离子的掺入。 (解决方案) 提供了一种由下述一般式表示的新型咪唑类化合物。其中，R1代表氢，直链或支链的1-11碳的烷基基团。R2代表独立的1-11碳的直链或支链的烷氧基团。R3代表独立的1-11碳的直链或支链的烷基、氯或溴。m是1到4的整数，n是0到4的整数。 新型咪唑类化合物 表面处理剂 印刷电路板

  公开号：

  KR101642378B1

文献信息

• Base-Mediated Syntheses of Di- and Trisubstituted Imidazoles from Amidine Hydrochlorides and Bromoacetylenes
  作者：Xiao Yun Chen、Ulli Englert、Carsten Bolm

  DOI：10.1002/chem.201502707

  日期：2015.9.14

  A new transition metal‐free method for the preparation of substituted imidazoles from easy‐to‐handle amidine hydrochlorides and bromoacetylenes has been developed. The reactions proceed in air and use inexpensive K2CO3 as base. Additions of 2,2′‐bipyridine and water have beneficial effects on the product yields. Various di‐ and trisubstituted imidazoles have been prepared in good yields (up to 88 %)

  已开发出一种新的无过渡金属的方法，该方法由易于处理的am盐酸盐和溴乙炔制备取代的咪唑。反应在空气中进行，并使用廉价的K 2 CO 3作为碱。添加2,2'-联吡啶和水对产品收率有有利影响。各种二，三取代的咪唑均以高收率（高达88％）制备。
• Identification and characterization of diarylimidazoles as hybrid inhibitors of butyrylcholinesterase and amyloid beta fibril formation
  作者：Daniela Karlsson、Adyary Fallarero、Gerda Brunhofer、Przemyslaw Guzik、Michaela Prinz、Ulrike Holzgrabe、Thomas Erker、Pia Vuorela

  DOI：10.1016/j.ejps.2011.11.004

  日期：2012.1

  In this contribution, a chemical collection of aromatic compounds was screened for inhibition on butyrylcholinesterase (BChE)'s hydrolase activity using Ellman's reaction. A set of diarylimidazoles was identified as highly selective inhibitors of BChE hydrolase activity and amyloid beta (A beta) fibril formation. New derivatives were synthesized resulting in several additional hits, from which the most active was 6c, 4-(3-ethylthiophenyl)-2-(3-thieny1)-1H-imidazole, an uncompetitive inhibitor of BChE hydrolase activity (IC50 BChE = 0.10 mu M; K-i = 0.073 +/- 0.011 mu M) acting also on Ap fibril formation (IC50 = 5.8 mu M). With the aid of structure-activity relationship (SAR) studies, chemical motifs influencing the BChE inhibitory activity of these imidazoles were proposed. These bifunctional inhibitors represent good tools in basic studies of BChE and/or promising lead molecules for AD therapy. (C) 2011 Elsevier B.V. All rights reserved.
• 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.
• CERTAIN DIARYLIMIDAZOLE DERIVATIVES; A NEW CLASS OF NPY SPECIFIC LIGANDS
  申请人：NEUROGEN CORPORATION

  公开号：EP0996443A1

  公开（公告）日：2000-05-03
• US6121260A
  申请人：——

  公开号：US6121260A

  公开（公告）日：2000-09-19