1,2-bis(4-methoxyphenyl)-4-(trifluoromethyl)-1H-imidazole | 868861-19-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,2-bis(4-methoxyphenyl)-4-(trifluoromethyl)-1H-imidazole
• 英文别名: 1,2-Bis(4-methoxyphenyl)-4-(trifluoromethyl)imidazole
• CAS: 868861-19-2
• 化学式: C₁₈H₁₅F₃N₂O₂
• 分子量: 348.325
• InChiKey: DYHDNJPXQRRBFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-bis(4-methoxyphenyl)-4-(trifluoromethyl)-1H-imidazole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以32%的产率得到4-[1-(4-Hydroxyphenyl)-4-(trifluoromethyl)imidazol-2-yl]phenol
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of 1H-Imidazoles as Ligands for the Estrogen Receptor and Cytotoxic Inhibitors of the Cyclooxygenase

  摘要：

  The 1H-imidazoles 7a-e were synthesized and tested for biological activity in vitro. The results pointed to a clear structure-activity relationship. The introduction of an ethyl chain at C5 of the 1,2,4-tris(4-hydroxyphenyl)-1H-imidazole 7a caused hormonal activity in estrogen receptor positive MCF-7-2a cells. An o-chlorine substituent in the phenolic rings at C2 and C4 as realized in 7b and 7c increased the antiproliferative effects against human breast cancer cell lines MCF-7 and MDA-MB 231. Additionally, both compounds showed strong inhibitory effects on cyclooxygenase enzymes. Therefore, a mode of action including the interference in the arachidonic acid cascade might be possible.

  DOI：

  10.1021/jm050190u
• 作为产物：
  描述：

  4-甲氧基苯甲腈 在 potassium carbonate 、 sodium amide 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 27.0h， 生成 1,2-bis(4-methoxyphenyl)-4-(trifluoromethyl)-1H-imidazole
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of 1H-Imidazoles as Ligands for the Estrogen Receptor and Cytotoxic Inhibitors of the Cyclooxygenase

  摘要：

  The 1H-imidazoles 7a-e were synthesized and tested for biological activity in vitro. The results pointed to a clear structure-activity relationship. The introduction of an ethyl chain at C5 of the 1,2,4-tris(4-hydroxyphenyl)-1H-imidazole 7a caused hormonal activity in estrogen receptor positive MCF-7-2a cells. An o-chlorine substituent in the phenolic rings at C2 and C4 as realized in 7b and 7c increased the antiproliferative effects against human breast cancer cell lines MCF-7 and MDA-MB 231. Additionally, both compounds showed strong inhibitory effects on cyclooxygenase enzymes. Therefore, a mode of action including the interference in the arachidonic acid cascade might be possible.

  DOI：

  10.1021/jm050190u