2-(11H-dibenzo<1,4>dioxepin-11-yl)-4,5-dihydro-1H-imidazole | 136093-67-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(11H-dibenzo<1,4>dioxepin-11-yl)-4,5-dihydro-1H-imidazole
• 英文别名: 2-(6H-benzo[b][1,4]benzodioxepin-6-yl)-4,5-dihydro-1H-imidazole
• CAS: 136093-67-9
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: AVVNTZBKWRZUKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  42.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(2-hydroxyphenoxy)-α-bromobenzeneacetic acid 在 吡啶 、 ammonium hydroxide 、 硫酸 、 sodium hydride 、 三氟乙酸酐 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 69.0h， 生成 2-(11H-dibenzo<1,4>dioxepin-11-yl)-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  Synthesis of new fenmetazole analogues with potential mixed α2-adrenergic antagonistic activity and noradrenaline-uptake inhibiting properties

  摘要：

  In the search for new antidepressants with a rapid onset of action, fenmetazole analogues, bearing a second phenyl ring in a position previously shown not to be detrimental to affinity and selectivity for the alpha-2-adrenoreceptors, were synthesized in an attempt to combine NA-uptake inhibition and blockade of the alpha-2-adrenoreceptors in the same molecule. Some of the new molecules showed enhanced affinity and selectivity for the alpha-2-adrenoreceptors compared to fenmetazole. Surprisingly, introduction of a phenyl ring in the structure of fenmetazole changed the agonistic action of the parent compound toward the alpha-1-adrenoreceptors into an antagonistic effect. However, none of the new derivatives showed in vitro NA-uptake inhibitory potency substantially different from the low activity of fenmetazole in this test.

  DOI：

  10.1016/0223-5234(91)90031-h

文献信息

• Synthesis of new fenmetazole analogues with potential mixed α2-adrenergic antagonistic activity and noradrenaline-uptake inhibiting properties
  作者：P Melloni、A Della Torre、M Meroni、P Pevarello、M Varasi、A Bonsignori、M Cini、F Vaghi、P Dostert

  DOI：10.1016/0223-5234(91)90031-h

  日期：1991.3

  In the search for new antidepressants with a rapid onset of action, fenmetazole analogues, bearing a second phenyl ring in a position previously shown not to be detrimental to affinity and selectivity for the alpha-2-adrenoreceptors, were synthesized in an attempt to combine NA-uptake inhibition and blockade of the alpha-2-adrenoreceptors in the same molecule. Some of the new molecules showed enhanced affinity and selectivity for the alpha-2-adrenoreceptors compared to fenmetazole. Surprisingly, introduction of a phenyl ring in the structure of fenmetazole changed the agonistic action of the parent compound toward the alpha-1-adrenoreceptors into an antagonistic effect. However, none of the new derivatives showed in vitro NA-uptake inhibitory potency substantially different from the low activity of fenmetazole in this test.