cis-2-(5-phenyl-1,4-dioxan-2-yl)-4,5-dihydro-1H-imidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: cis-2-(5-phenyl-1,4-dioxan-2-yl)-4,5-dihydro-1H-imidazole
• 英文别名: 2-[(2R,5R)-5-phenyl-1,4-dioxan-2-yl]-4,5-dihydro-1H-imidazole
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: MPFNVJVLRBBPHX-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  cis-5-phenyl-1,4-dioxane-2-carboxylic acid 在 硫酸 、 三甲基铝 作用下， 以 甲苯 为溶剂， 反应 9.0h， 生成 cis-2-(5-phenyl-1,4-dioxan-2-yl)-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  Favourable involvement of α2A-adrenoreceptor antagonism in the I2-imidazoline binding sites-mediated morphine analgesia enhancement

  摘要：

  Aim of the present study was to obtain novel alpha(2)-adrenoreceptor (alpha(2)-AR) antagonists, possibly endowed with subtype-selectivity. Therefore, inspired by the non subtype-selective alpha(2)-AR antagonist idazoxan, we designed 1,4-dioxane derivatives bearing an aromatic area in position 5 or 6 and the imidazoline nucleus in position 2. Among the novel molecules 1-6, compound 2, with a trans stereochemical relationship between 5-phenyl and 2-imidazoline groups, was able to antagonize the sole alpha(2A)-subtype. Moreover, 2 showed an affinity at I-2-imidazoline binding sites (I-2-IBS) comparable to that at alpha(2A)-AR. In in vivo studies 2 strongly increased morphine analgesia. This interesting behaviour appeared to be induced by the favourable involvement of alpha(2A)-AR antagonism in the I-2-IBS-mediated morphine analgesia enhancement. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.016