2,4-bis(2-chloro-4-methoxyphenyl)-1-(4-methoxyphenyl)-5-methyl-1H-imidazole | 935750-30-4

• 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-bis(2-chloro-4-methoxyphenyl)-1-(4-methoxyphenyl)-5-methyl-1H-imidazole
• 英文别名: 2,4-Bis(2-chloro-4-methoxyphenyl)-1-(4-methoxyphenyl)-5-methylimidazole
• CAS: 935750-30-4
• 化学式: C₂₅H₂₂Cl₂N₂O₃
• 分子量: 469.367
• InChiKey: TZVLUNJOLNVDMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-bis(2-chloro-4-methoxyphenyl)-1-(4-methoxyphenyl)-5-methyl-1H-imidazole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以78%的产率得到2,4-bis(2-chloro-4-hydroxyphenyl)-1-(4-hydroxyphenyl)-5-methyl-1H-imidazole
  参考文献：
  名称：

  Structure−Activity Relationship Study To Understand the Estrogen Receptor-Dependent Gene Activation of Aryl- and Alkyl-Substituted 1H-Imidazoles

  摘要：

  A series of C5-substituted 1,2,4-triaryl-1H-imidazoles was synthesized. Their gene-activating properties were determined on estrogen receptor alpha positive MCF-7 breast cancer cells, stably transfected with the plasmid ERE(wtc)luc (MCF-7-2a cells). The influence of 4-OH and 2-Cl substituents on the phenyl rings as well as the significance of a methyl, ethyl, or phenyl group at C5 on the estrogen receptor binding and the resulting gene activation in MCF-7-2a cells was studied. The alkyl and aryl groups at C5 of 1,2,4-tris(4-hydroxyphenyl)-1H-imidazole 1 increased the transactivation, while chlorine atoms on the phenyl rings diminished this effect. 5-Ethyl-1,2,4-tris(4-hydroxyphenyl)-1H-imidazole 9 was identified as the most active compound. Its excellent transcriptional activity did not only depend on the C5 ethyl group, but also on the three hydroxyl groups of the phenyl rings. Compounds (11-14) with a reduced number of hydroxyl groups displayed distinctly lower gene activation.

  DOI：

  10.1021/jm061106t
• 作为产物：
  描述：

  2-氯-4-羟基苯甲醛 在 lead(IV) acetate 氨 、 potassium carbonate 、 sodium amide 作用下， 以 氯仿 、 水 、 甲苯 为溶剂， 反应 78.0h， 生成 2,4-bis(2-chloro-4-methoxyphenyl)-1-(4-methoxyphenyl)-5-methyl-1H-imidazole
  参考文献：
  名称：

  Structure−Activity Relationship Study To Understand the Estrogen Receptor-Dependent Gene Activation of Aryl- and Alkyl-Substituted 1H-Imidazoles

  摘要：

  A series of C5-substituted 1,2,4-triaryl-1H-imidazoles was synthesized. Their gene-activating properties were determined on estrogen receptor alpha positive MCF-7 breast cancer cells, stably transfected with the plasmid ERE(wtc)luc (MCF-7-2a cells). The influence of 4-OH and 2-Cl substituents on the phenyl rings as well as the significance of a methyl, ethyl, or phenyl group at C5 on the estrogen receptor binding and the resulting gene activation in MCF-7-2a cells was studied. The alkyl and aryl groups at C5 of 1,2,4-tris(4-hydroxyphenyl)-1H-imidazole 1 increased the transactivation, while chlorine atoms on the phenyl rings diminished this effect. 5-Ethyl-1,2,4-tris(4-hydroxyphenyl)-1H-imidazole 9 was identified as the most active compound. Its excellent transcriptional activity did not only depend on the C5 ethyl group, but also on the three hydroxyl groups of the phenyl rings. Compounds (11-14) with a reduced number of hydroxyl groups displayed distinctly lower gene activation.

  DOI：

  10.1021/jm061106t