2,4(5)-diphenylimidazole hydrochloride | 53316-52-2

• 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)-diphenylimidazole hydrochloride
• 英文别名: 2,4-diphenyl-1(3)H-imidazole; hydrochloride；2,4-Diphenyl-1(3)H-imidazol; Hydrochlorid；2,4-Diphenyl-imidazol Hydrochlorid；2,5-diphenyl-1H-imidazole;hydrochloride
• CAS: 53316-52-2
• 化学式: C₁₅H₁₂N₂*ClH
• 分子量: 256.735
• InChiKey: HBVOSRPDQHKAIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  18
• 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：
  28.7
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,4-二苯基咪唑 在 盐酸 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 2,4(5)-diphenylimidazole 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

文献信息

• Minovici, Chemische Berichte, 1896, vol. 29, p. 2100
  作者：Minovici

  DOI：——

  日期：——
• Burtles; Pyman, Journal of the Chemical Society, 1923, vol. 123, p. 362,364
  作者：Burtles、Pyman

  DOI：——

  日期：——
• 2,4(5)-Diarylimidazoles as inhibitors of hNaV1.2 sodium channels: Pharmacological evaluation and structure–property relationships
  作者：Marco Fantini、Mirko Rivara、Valentina Zuliani、Christopher L. Kalmar、Federica Vacondio、Claudia Silva、Aparna R. Baheti、Natasha Singh、Ellen C. Merrick、Ravi S. Katari、Giuseppe Cocconcelli、Chiara Ghiron、Manoj K. Patel

  DOI：10.1016/j.bmc.2009.03.067

  日期：2009.5

  Sodium (Na) channels continue to represent an important target for the development of novel anticonvulsants. We have synthesized and evaluated a series of 2,4(5)-diarylimidazoles for inhibition of the human neuronal Na(V)1.2 Na channel isoform. Starting with the unsubstituted lead compound previously published 3, SAR studies were performed introducing substituents with different physico-chemical properties. Lipophilicity (log D-7.4) and basicity (pK(a)) of the compounds were measured and submitted for QSPR investigations. Some of the active compounds described had IC50 values that were considerably lower than our lead compound. In particular, the m-CF3 disubstituted 22 was the most active compound, inhibiting hNa(V)1.2 currents within the nanomolar concentration range (IC50 = 200 nM). In comparison, lamotrigine and phenytoin, two clinically used anticonvulsant drugs known to inhibit Na channels, had IC50's values that were greater than 100 mu M. (C) 2009 Elsevier Ltd. All rights reserved.