1-(2,4-difluorophenyl)-1-(4-bromophenyl)-2-(1-imidazolyl)-1-ethanol | 142657-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2,4-difluorophenyl)-1-(4-bromophenyl)-2-(1-imidazolyl)-1-ethanol
• 英文别名: 1-(4-Bromophenyl)-1-(2,4-difluorophenyl)-2-imidazol-1-ylethanol
• CAS: 142657-49-6
• 化学式: C₁₇H₁₃BrF₂N₂O
• 分子量: 379.204
• InChiKey: CWNRDWMRRVRLQR-UHFFFAOYSA-N

物化性质

• 沸点：
  561.4±50.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(三甲基锡烷基)-吡啶 、 1-(2,4-difluorophenyl)-1-(4-bromophenyl)-2-(1-imidazolyl)-1-ethanol 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以13%的产率得到1-(2,4-difluorophenyl)-2-imidazol-1-yl-1-(4-pyridin-3-ylphenyl)ethanol
  参考文献：
  名称：

  Novel 1-(pyridylphenyl)-1-phenyl-2-imidazolylethanols with topical antiinflammatory activity

  摘要：

  The synthesis, biological evaluation, and structure-activity relationships of a series of 1-(pyridylphenyl)-1-phenyl-2-imidazolylethanols are described. These compounds show potent dose-dependent topical antiinflammatory activity in murine models of skin inflammation. This effect is likely due to inhibition of cytochrome P450 and consequent reduction in levels of 12R-HETE in the skin. These compounds were examined for their ability to inhibit the oxidative metabolism of arachidonic acid; they specifically inhibit the formation of prostacyclins in mouse macrophages. To study the effects of structure on the in vivo activity, three general features of the molecules were varied: the position of attachment of the pyridine nucleus (A), the second aromatic residue (B), and the nitrogen base on the ethanol chain (C). 1-[4-(4-Pyridyl)phenyl]-1-(4-fluorophenyl)-2-imidazolylethanol (2a, DuP 983) shows a very attractive profile of antiinflammatory activity and has been selected for clinical evaluation as a topical antiinflammatory agent.

  DOI：

  10.1021/jm00095a009
• 作为产物：
  描述：

  4-溴苯基锂 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 1-(2,4-difluorophenyl)-1-(4-bromophenyl)-2-(1-imidazolyl)-1-ethanol
  参考文献：
  名称：

  Novel 1-(pyridylphenyl)-1-phenyl-2-imidazolylethanols with topical antiinflammatory activity

  摘要：

  The synthesis, biological evaluation, and structure-activity relationships of a series of 1-(pyridylphenyl)-1-phenyl-2-imidazolylethanols are described. These compounds show potent dose-dependent topical antiinflammatory activity in murine models of skin inflammation. This effect is likely due to inhibition of cytochrome P450 and consequent reduction in levels of 12R-HETE in the skin. These compounds were examined for their ability to inhibit the oxidative metabolism of arachidonic acid; they specifically inhibit the formation of prostacyclins in mouse macrophages. To study the effects of structure on the in vivo activity, three general features of the molecules were varied: the position of attachment of the pyridine nucleus (A), the second aromatic residue (B), and the nitrogen base on the ethanol chain (C). 1-[4-(4-Pyridyl)phenyl]-1-(4-fluorophenyl)-2-imidazolylethanol (2a, DuP 983) shows a very attractive profile of antiinflammatory activity and has been selected for clinical evaluation as a topical antiinflammatory agent.

  DOI：

  10.1021/jm00095a009

文献信息

• Novel 1-(pyridylphenyl)-1-phenyl-2-imidazolylethanols with topical antiinflammatory activity
  作者：Stephen W. Wright、Richard R. Harris、Robert J. Collins、Ronald L. Corbett、Alicia M. Green、Eric A. Wadman、Douglas G. Batt

  DOI：10.1021/jm00095a009

  日期：1992.8

  The synthesis, biological evaluation, and structure-activity relationships of a series of 1-(pyridylphenyl)-1-phenyl-2-imidazolylethanols are described. These compounds show potent dose-dependent topical antiinflammatory activity in murine models of skin inflammation. This effect is likely due to inhibition of cytochrome P450 and consequent reduction in levels of 12R-HETE in the skin. These compounds were examined for their ability to inhibit the oxidative metabolism of arachidonic acid; they specifically inhibit the formation of prostacyclins in mouse macrophages. To study the effects of structure on the in vivo activity, three general features of the molecules were varied: the position of attachment of the pyridine nucleus (A), the second aromatic residue (B), and the nitrogen base on the ethanol chain (C). 1-[4-(4-Pyridyl)phenyl]-1-(4-fluorophenyl)-2-imidazolylethanol (2a, DuP 983) shows a very attractive profile of antiinflammatory activity and has been selected for clinical evaluation as a topical antiinflammatory agent.