2-(4-chlorophenyl)-4(5)-(3-trifluoromethylphenyl)imidazole | 162701-76-0

• 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-chlorophenyl)-4(5)-(3-trifluoromethylphenyl)imidazole
• 英文别名: 2-(4-Chlorophenyl)-4(5)-(3-trifluoromethylphenyl)-imidazole；2-(4-chlorophenyl)-5-[3-(trifluoromethyl)phenyl]-1H-imidazole
• CAS: 162701-76-0
• 化学式: C₁₆H₁₀ClF₃N₂
• 分子量: 322.717
• InChiKey: NEKKFGFJEMKNNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 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-chlorophenyl)-4(5)-(3-trifluoromethylphenyl)imidazole 在 盐酸 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 2-(4-chlorophenyl)-4(5)-(3-trifluoromethylphenyl)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

文献信息

• IMIDAZOLE DERIVATIVE, PROCESS FOR PRODUCING THE SAME, AND PEST CONTROL DRUG
  申请人：NIPPON SODA CO., LTD.

  公开号：EP0712847A1

  公开（公告）日：1996-05-22

  An imidazole derivative represented by general formula [I], which has insecticidal, acaricidal and agrohorticultural bactericidal activities, wherein R¹ represents phenyl which may be substituted by halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆-alkoxy-substituted C₁-C₆ alkoxy, optionally substituted phenyl, optionally substituted pyridyl, optionally substituted phenoxy, optionally substituted pyridyloxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₆ alkynyloxy, C₂-C₆ haloalkylnyloxy, nitro, C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylsulfonyl, di(C₁-C₆ alkyl) sulfamoyl, cyano, C₁-C₆ alkoxycarbonyl or C₁-C₆ alkylcarbonyl, or which may be fused with a benzene ring to form naphthyl; R² represents C₁-C₆ alkoxycarbonyl, C₁-C₆-alkoxy-substituted C₁-C₆ alkoxycarbonyl, cyano r¹r²NCO (wherein r¹ and r² represent each hydrogen, C₁-C₆ alkyl or optionally substituted phenyl), C₁-C₆ alkylthiocarbonyl, C₁-C₆ alkoxycarboimidoyl, carboxy, halogen, C₁-C₆ haloalkyl, formyl or nitro; R³ represents hydrogen, optionally halogenated phenyl, C₁-C₆ haloalkyl, C₁-C₁₂ alkyl, benzoyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbonyl, aralkyl or C₃-C₇ cycloalkyl; and R⁴ represents hydrogen, C₁-C₆ alkyl (which may be substituted by C₁-C₆ alkoxy, optionally substituted aralkyloxy, C₁-C₆-alkoxy-substituted C₁-C₆ alkoxy, C₁-C₆ acyloxy, C₁-C₆ alkoxycarbonyloxy, C₁-C₆ acylamido, C₂-C₆ alkenyloxy, C₂-C₆ alkynyloxy, r³SOn (wherein r³ represents C₁-C₆ alkyl or optionally substituted phenyl, and n represents an integer of 0 to 2), optionally substituted benzoyl, C₁-C₆ alkoxycarbonyl, di(C₁-C₆ alkyl) phosphinyl, cyano or thiocyanato), aralkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ alkylcarbonyl or cyano, provided R² and R⁴ may form together a ring.

  通式[I]代表的咪唑衍生物，具有杀虫、杀螨剂和农用园艺杀菌活性，其中 R¹ 代表可被卤素取代的苯基、C₁-C₆烷基、C₁-C₆卤代烷基、C₁-C₆烷氧基、C₁-C₆卤代烷氧基、C₁-C₆-烷氧基取代的 C₁-C₆烷氧基、任选取代的苯基、任选取代的吡啶基、C₂-C₆烯氧基、C₂-C₆卤代烯氧基、C₂-C₆炔氧基、C₂-C₆卤代炔氧基、硝基、C₁-C₆烷硫基、C₁-C₆烷基亚磺酰基、C₁-C₆烷基磺酰基、二（C₁-C₆烷基）氨基磺酰基、氰基、C₁-C₆烷氧基羰基或 C₁-C₆烷基羰基，或可与苯环融合形成萘基；R² 代表 C₁-C₆烷氧基羰基、C₁-C₆-烷氧基取代的 C₁-C₆ 烷氧基羰基、氰基 r¹r²NCO（其中 r¹ 和 r² 各自代表氢、C₁-C₆烷基或任选取代的苯基）、C₁-C₆烷硫基羰基、C₁-C₆烷氧基羰酰亚胺基、羧基、卤素、C₁-C₆卤代烷基、甲酰基或硝基；R³ 代表氢、任选卤代苯基、C₁-C₆卤代烷基、C₁-C₁₂烷基、苯甲酰基、C₁-C₆烷氧基羰基、C₁-C₆烷基羰基、芳基或 C₃-C₇ 环烷基；R⁴ 代表氢、C₁-C₆ 烷基（可被 C₁-C₆烷氧基、任选取代的芳烷氧基取代、C₁-C₆-烷氧基取代的 C₁-C₆烷氧基、C₁-C₆酰氧基、C₁-C₆烷氧基羰基氧基、C₁-C₆酰氨基、C₂-C₆烯氧基、C₂-C₆炔氧基、r³SOn（其中 r³ 代表 C₁-C₆烷基或任选取代的苯基，n 代表 0 至 2 的整数）、任选取代的苯甲酰基、C₁-C₆烷氧羰基、二（C₁-C₆烷基）膦酰基、氰基或硫氰酸基）、芳烷基、C₂-C₆烯基、C₂-C₆炔基、C₁-C₆烷基羰基或氰基，条件是 R² 和 R⁴ 可共同形成一个环。