2-(4-Amino-phenyl)-1-(2,4-dichloro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester | 850339-34-3

• 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-Amino-phenyl)-1-(2,4-dichloro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester
• 英文别名: ethyl 2-(4-aminophenyl)-1-(2,4-dichlorophenyl)imidazole-4-carboxylate
• CAS: 850339-34-3
• 化学式: C₁₈H₁₅Cl₂N₃O₂
• 分子量: 376.242
• InChiKey: CTWMONZOQPBQSN-UHFFFAOYSA-N

物化性质

• 熔点：
  217-219 °C(Solv: chloroform (67-66-3); methanol (67-56-1))
• 沸点：
  572.8±60.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-Amino-phenyl)-1-(2,4-dichloro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester 在 盐酸 、 sodium nitrite 、 potassium iodide 作用下， 反应 5.5h， 以74%的产率得到1-(2,4-Dichloro-phenyl)-2-(4-iodo-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis, Structure−Activity Relationships at the GABA_A Receptor in Rat Brain, and Differential Electrophysiological Profile at the Recombinant Human GABA_A Receptor of a Series of Substituted 1,2-Diphenylimidazoles

  摘要：

  A series of new 1,2-diphenylimidazole derivatives (la-x) were synthesized and evaluated for their ability to potentiate gamma-aminobutyric acid (GABA)-evoked currents in Xenopus laevis oocytes expressing recombinant human GABAA receptors. Many of these compounds enhanced GABA action with potencies (EC50 = 0.19-19,mu M) and efficacies (maximal efficacies of up to 640%) similar to or greater than those of anesthetics such as etomidate, propofol, and alphaxalone. Structure- activity relationship analysis revealed that the presence of an ester moiety in the imidazole ring was required for full agonist properties, while modifications made in the phenyl rings affected potency and efficacy, with ethyl 2-(4-bromophenyl)-l-(2,4-dichlorophenyl)-1H4-imidazolecarboxylate showing the highest potency. These compounds potentiated the [H-3]GABA binding to rat brain membranes, suggesting a site of interaction different from that of GABA. As for etomidate, mutation of asparagine-265 in the beta 2 subunit of the GABA(A) receptor into serine reduced the ability of derivative 1i to modulate the GABA function.

  DOI：

  10.1021/jm049120y
• 作为产物：
  描述：

  对硝基苯甲腈 在 盐酸 、 三甲基铝 、 碳酸氢钠 、 对甲苯磺酸 、 tin(ll) chloride 作用下， 以 甲醇 、 异丙醇 、 甲苯 为溶剂， 反应 4.0h， 生成 2-(4-Amino-phenyl)-1-(2,4-dichloro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis, Structure−Activity Relationships at the GABA_A Receptor in Rat Brain, and Differential Electrophysiological Profile at the Recombinant Human GABA_A Receptor of a Series of Substituted 1,2-Diphenylimidazoles

  摘要：

  A series of new 1,2-diphenylimidazole derivatives (la-x) were synthesized and evaluated for their ability to potentiate gamma-aminobutyric acid (GABA)-evoked currents in Xenopus laevis oocytes expressing recombinant human GABAA receptors. Many of these compounds enhanced GABA action with potencies (EC50 = 0.19-19,mu M) and efficacies (maximal efficacies of up to 640%) similar to or greater than those of anesthetics such as etomidate, propofol, and alphaxalone. Structure- activity relationship analysis revealed that the presence of an ester moiety in the imidazole ring was required for full agonist properties, while modifications made in the phenyl rings affected potency and efficacy, with ethyl 2-(4-bromophenyl)-l-(2,4-dichlorophenyl)-1H4-imidazolecarboxylate showing the highest potency. These compounds potentiated the [H-3]GABA binding to rat brain membranes, suggesting a site of interaction different from that of GABA. As for etomidate, mutation of asparagine-265 in the beta 2 subunit of the GABA(A) receptor into serine reduced the ability of derivative 1i to modulate the GABA function.

  DOI：

  10.1021/jm049120y