(R)-(-)-2-(3,4,α-trihydroxybenzyl)imidazoline hydrochloride | 75847-71-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (R)-(-)-2-(3,4,α-trihydroxybenzyl)imidazoline hydrochloride
• 英文别名: 4-[(R)-4,5-dihydro-1H-imidazol-2-yl(hydroxy)methyl]benzene-1,2-diol;hydrochloride
• CAS: 75847-71-1
• 化学式: C₁₀H₁₂N₂O₃*ClH
• 分子量: 244.678
• InChiKey: AKQBHQAYJIKOLI-SBSPUUFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.55
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  85.1
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (+/-)-2-<3,4-bis(benzyloxy)-α-hydroxybenzyl>imidazoline 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (R)-(-)-2-(3,4,α-trihydroxybenzyl)imidazoline hydrochloride
  参考文献：
  名称：

  Optically active catecholimidazolines: a study of steric interactions at .alpha.-adrenoreceptors

  摘要：

  The optical isomers and deoxy form of 2-(3,4, alpha-trihydroxybenzyl)imidazoline hydrochloride were examined for their alpha-adrenergic activity on rat aorta. The rank order of stimulant activity was deoxy (2) congruent to (R)-(-)-1 greater than (S)-(+)-1. This is in contrast to catecholamines in which the order of activity is (R)-(-)-epinephrine greater than (S)-(+)-epinephrine = epinine (deoxyepinephrine). The relative order of potency for the isomers of 2-(3,4, alpha-trihydroxybenzyl)imidazoline is different than that predicted by the Easson--Stedman theory for stereoisomers of catecholamines. Also, substitution of the deoxy compound 2 with substituents, methyl or benzyl, in the 4-position lowers the alpha-adrenergic agonist activity, and differences observed between optical isomers were small.

  DOI：

  10.1021/jm00361a005

文献信息

• Optically active catecholimidazolines: a study of steric interactions at .alpha.-adrenoreceptors
  作者：Duane D. Miller、Akihiko Hamada、Edward C. Craig、Gary G. Christoph、Judith C. Galluci、Peter J. Rice、Jon W. Banning、Popat N. Patil

  DOI：10.1021/jm00361a005

  日期：1983.7

  The optical isomers and deoxy form of 2-(3,4, alpha-trihydroxybenzyl)imidazoline hydrochloride were examined for their alpha-adrenergic activity on rat aorta. The rank order of stimulant activity was deoxy (2) congruent to (R)-(-)-1 greater than (S)-(+)-1. This is in contrast to catecholamines in which the order of activity is (R)-(-)-epinephrine greater than (S)-(+)-epinephrine = epinine (deoxyepinephrine). The relative order of potency for the isomers of 2-(3,4, alpha-trihydroxybenzyl)imidazoline is different than that predicted by the Easson--Stedman theory for stereoisomers of catecholamines. Also, substitution of the deoxy compound 2 with substituents, methyl or benzyl, in the 4-position lowers the alpha-adrenergic agonist activity, and differences observed between optical isomers were small.