3-(4-phenyl-1H-imidazol-2-yl)pyridine | 59282-86-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-phenyl-1H-imidazol-2-yl)pyridine
• 英文别名: 3-(4(5)-phenylimidazol-2-yl)pyridine；4-phenyl-2-(3-pyridyl)imidazole；3-(4-phenyl-1(3)H-imidazol-2-yl)-pyridine；3-(4-phenyl-1H-imidazol-2-yl)-pyridine；3-(5-phenyl-1H-imidazol-2-yl)pyridine
• CAS: 59282-86-9
• 化学式: C₁₄H₁₁N₃
• 分子量: 221.261
• InChiKey: LTCDTRSZRYCRBC-UHFFFAOYSA-N

物化性质

• 熔点：
  201-203 °C
• 沸点：
  493.7±28.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 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：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-phenyl-1H-imidazol-2-yl)pyridine 、 碘甲烷 在 sodium hydride 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 3.0h， 生成 3-(1-methyl-4-phenyl-1H-imidazol-2-yl)-pyridine
  参考文献：
  名称：

  Neurokinin-3 receptor modulators: diaryl imidazole derivatives

  摘要：

  该发明涉及一般式I的化合物： 其中变量如本文所定义。还提供包含这种化合物的药物组合物，以及治疗对神经激肽-3受体调节敏感的患者的方法。本文提供的NK-3受体调节剂也可用作定位NK-3受体的探针。

  公开号：

  US20050148601A1
• 作为产物：
  描述：

  苯乙烯 在 碘 、 potassium carbonate 、 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 3-(4-phenyl-1H-imidazol-2-yl)pyridine
  参考文献：
  名称：

  Direct preparation of thiazoles, imidazoles, imidazopyridines and thiazolidines from alkenes

  摘要：

  通过两步酮亚胺化/环化方案，一系列杂环化合物，包括噻唑、咪唑、咪唑并吡啶、噻唑烷和二甲氧基吲哚，已直接从烯烃合成。烯烃起始原料可通过多种不同且成熟的途径轻松获得，并能以优异的产率和区域选择性制备多种杂环化合物。

  DOI：

  10.1039/c1ob06587d

文献信息

• Direct Preparation of Heteroaromatic Compounds from Alkenes
  作者：Timothy Donohoe、Mikhail Kabeshov、Akshat Rathi、Ian Smith

  DOI：10.1055/s-0030-1259034

  日期：2010.12

  A series of aromatic heterocycles, thiazoles, imidazoles, and dimethoxyindoles, can be synthesised directly from alkenes via a ketoiodination-cyclisation protocol. The alkene starting materials are themselves easily accessible by many different and well-established approaches, and allow access to various aromatic heterocycles with excellent yields and regioselectivity.

  一系列芳香杂环、噻唑、咪唑和二甲氧基吲哚，可以通过酮碘化-环化方案直接从烯烃合成。烯烃原料本身很容易通过许多不同的和完善的方法获得，并允许以优异的产率和区域选择性获得各种芳族杂环。
• 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。
• Structure–activity relationship studies on 2-heteroaryl-4-arylimidazoles NPY5 receptor antagonists
  作者：Richard L. Elliott、Robert M. Oliver、Janet A. LaFlamme、Melissa L. Gillaspy、Marlys Hammond、Richard F. Hank、Tristan S. Maurer、Demetria L. Baker、Paul A. DaSilva-Jardine、Ralph W. Stevenson、Christine M. Mack、James V. Cassella

  DOI：10.1016/s0960-894x(03)00747-9

  日期：2003.10

  A series of 2-heteroaryl-4-arylimidazoles with potent in vitro activity at the NPY5 receptor was developed. Introduction of electron-withdrawing groups on the 4-aryl ring led to a significant improvement of in vitro potency. Several analogues from this series had anorectic activity in rodent feeding models, but were also found to have undesired behavioral effects in spontaneous locomotor activity. (C) 2003 Elsevier Ltd. All rights reserved.
• 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.
• 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.