2-(7-phenyl-2,3-dihydro-1,4-benzodioxin-2-yl)-4,5-dihydro-1H-imidazole | 1043534-02-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 2-(7-phenyl-2,3-dihydro-1,4-benzodioxin-2-yl)-4,5-dihydro-1H-imidazole
• 英文别名: 2-(6-phenyl-2,3-dihydro-1,4-benzodioxin-3-yl)-4,5-dihydro-1H-imidazole
• CAS: 1043534-02-6
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: CENDKGWAICPCEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  联苯-3,4-二醇 、 乙二胺 、 2-氯丙烯腈 在 potassium carbonate 、 盐酸 作用下， 以 丙酮 、 甲醇 、 氯仿 为溶剂， 反应 30.0h， 生成 2-(7-phenyl-2,3-dihydro-1,4-benzodioxin-2-yl)-4,5-dihydro-1H-imidazole 、 2-(6-phenyl-2,3-dihydro-1,4-benzodioxin-2-yl)-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  α₂-Adrenoreceptors Profile Modulation. 4. From Antagonist to Agonist Behavior

  摘要：

  The goal of the present study was to modulate the receptor interaction properties of known alpha(2)-adrenoreceptor (AR) antagonists to obtain novel alpha(2)-AR agonists with desirable subtype selectivity. Therefore, a phenyl group or one of its bioisosteres or aliphatic moieties with similar steric hindrance were introduced into the aromatic ring of the antagonist lead basic structure. The functional properties of the novel compounds allowed our previous observations to be confirmed. The high efficacy of 7, 12, and 13 as alpha(2)-AR agonists and the significant alpha(2C)-AR subtype selective activation displayed by 11 and 15 demonstrated that favorable interactions to induce alpha(2)-AR activation were formed between the pendant groups of the ligands and the aromatic cluster present in transmembrane domain 6 of the binding site cavity of the receptors.

  DOI：

  10.1021/jm800250z

文献信息

• α₂-Adrenoreceptors Profile Modulation. 4. From Antagonist to Agonist Behavior
  作者：Francesco Gentili、Claudia Cardinaletti、Cristian Vesprini、Antonio Carrieri、Francesca Ghelfi、Aniket Farande、Mario Giannella、Alessandro Piergentili、Wilma Quaglia、Jonne M. Laurila、Anna Huhtinen、Mika Scheinin、Maria Pigini

  DOI：10.1021/jm800250z

  日期：2008.7.1

  The goal of the present study was to modulate the receptor interaction properties of known alpha(2)-adrenoreceptor (AR) antagonists to obtain novel alpha(2)-AR agonists with desirable subtype selectivity. Therefore, a phenyl group or one of its bioisosteres or aliphatic moieties with similar steric hindrance were introduced into the aromatic ring of the antagonist lead basic structure. The functional properties of the novel compounds allowed our previous observations to be confirmed. The high efficacy of 7, 12, and 13 as alpha(2)-AR agonists and the significant alpha(2C)-AR subtype selective activation displayed by 11 and 15 demonstrated that favorable interactions to induce alpha(2)-AR activation were formed between the pendant groups of the ligands and the aromatic cluster present in transmembrane domain 6 of the binding site cavity of the receptors.