1,1-dimethylethyl cis-4,5-dihydro-2-(1,2,3,4-tetrahydro-1,3-dimethyl-2-quinolinyl)-1H-imidazole-1-carboxylate | 108797-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1,1-dimethylethyl cis-4,5-dihydro-2-(1,2,3,4-tetrahydro-1,3-dimethyl-2-quinolinyl)-1H-imidazole-1-carboxylate
• CAS: 108797-21-3
• 化学式: C₁₉H₂₇N₃O₂
• 分子量: 329.442
• InChiKey: WTYMITYRWVBOBD-CJNGLKHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  45.14
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl cis-4,5-dihydro-2-(1,2,3,4-tetrahydro-1,3-dimethyl-2-quinolinyl)-1H-imidazole-1-carboxylate 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以2.45 g的产率得到cis-2-(4,5-dihydro-1H-imidazol-2-yl)-1,2,3,4-tetrahydro-1,3-dimethylquinoline
  参考文献：
  名称：

  .alpha.2-Adrenergic agonists/antagonists: the synthesis and structure-activity relationships of a series of indolin-2-yl and tetrahydroquinolin-2-yl imidazolines

  摘要：

  The synthesis and alpha 2-adrenergic activity of a series of indolin-2-yl and tetrahydroquinolin-2-yl imidazolines are described. The indolin-2-yl imidazoline 4b was found to possess potent alpha 2-adrenergic agonist and antagonist activity. The modification of the substituents on the indoline ring of 4b has led to the separation of these activities. Substitution on the aromatic ring of 4b with halogen or increasing the size of the N-alkyl substituent of 4b gave alpha 2-adrenergic antagonists without agonist activity. The N-allylindoline 4d is more potent than idazoxan in vitro and is equipotent in vivo, but is less receptor selective (alpha 2 vs. alpha 1) than idazoxan. The cis-1,3-dimethylindolin-2-yl imidazoline 6a is an alpha 2-adrenergic agonist equal in potency to clonidine in vitro, while the trans-1,3-dimethylindolin-2-yl imidazoline 6b is a moderately potent alpha 2-adrenergic antagonist.

  DOI：

  10.1021/jm00392a005
• 作为产物：
  描述：

  2-(4,5-dihydro-1H-imidazol-2-yl)-3-methylquinoline 在 platinum(IV) oxide 盐酸 、 氢气 、 sodium cyanoborohydride 、 溶剂黄146 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 乙腈 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 8.5h， 生成 1,1-dimethylethyl cis-4,5-dihydro-2-(1,2,3,4-tetrahydro-1,3-dimethyl-2-quinolinyl)-1H-imidazole-1-carboxylate
  参考文献：
  名称：

  .alpha.2-Adrenergic agonists/antagonists: the synthesis and structure-activity relationships of a series of indolin-2-yl and tetrahydroquinolin-2-yl imidazolines

  摘要：

  The synthesis and alpha 2-adrenergic activity of a series of indolin-2-yl and tetrahydroquinolin-2-yl imidazolines are described. The indolin-2-yl imidazoline 4b was found to possess potent alpha 2-adrenergic agonist and antagonist activity. The modification of the substituents on the indoline ring of 4b has led to the separation of these activities. Substitution on the aromatic ring of 4b with halogen or increasing the size of the N-alkyl substituent of 4b gave alpha 2-adrenergic antagonists without agonist activity. The N-allylindoline 4d is more potent than idazoxan in vitro and is equipotent in vivo, but is less receptor selective (alpha 2 vs. alpha 1) than idazoxan. The cis-1,3-dimethylindolin-2-yl imidazoline 6a is an alpha 2-adrenergic agonist equal in potency to clonidine in vitro, while the trans-1,3-dimethylindolin-2-yl imidazoline 6b is a moderately potent alpha 2-adrenergic antagonist.

  DOI：

  10.1021/jm00392a005