5-Fluoro-1-(3,4,5-trimethoxy-benzyl)-1,2,3,4-tetrahydro-isoquinoline-6,7-diol; hydrochloride | 104716-86-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 5-Fluoro-1-(3,4,5-trimethoxy-benzyl)-1,2,3,4-tetrahydro-isoquinoline-6,7-diol; hydrochloride
• 英文别名: 5-Fluoro-1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol;hydrochloride
• CAS: 104716-86-1
• 化学式: C₁₉H₂₂FNO₅*ClH
• 分子量: 399.847
• InChiKey: YLGWHXLCNDGBHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  80.2
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6,7-Bis-benzyloxy-5-fluoro-1-(3,4,5-trimethoxy-benzyl)-1,2,3,4-tetrahydro-isoquinoline; hydrochloride 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、310.27 kPa 条件下， 反应 8.0h， 以65%的产率得到5-Fluoro-1-(3,4,5-trimethoxy-benzyl)-1,2,3,4-tetrahydro-isoquinoline-6,7-diol; hydrochloride
  参考文献：
  名称：

  5-Fluoro- and 8-fluorotrimetoquinol: selective .beta.2-adrenoceptor agonists

  摘要：

  The 5-fluoro and 8-fluoro analogues of trimetoquinol, TMQ, have been synthesized and evaluated for beta 2- and beta 1-adrenoceptor activity in guinea pig trachea and atria, respectively. The fluoro analogues of TMQ maintained potent beta 2-adrenoceptor agonist activity but had reduced beta 1-adrenoceptor agonist activity. The changes in beta 1-activity of these compounds were correlated to differences in phenolic pKa's. The beta 1- and beta 2-adrenoceptor actions of 2 and 3 were blocked in a competitive manner by propranolol. The enhanced beta 2/beta 1 selectivity for the analogues was found to be 8-fluoro analogue 3 greater than 5-fluoro analogue 2 greater than trimetoquinol (1).

  DOI：

  10.1021/jm00384a015

文献信息

• CLARK M. T.; ADEJARE A.; SHAMS G.; FELLER D. R.; MILLER D. D., J. MED. CHEM., 30,(1987) N 1, 86-90
  作者：CLARK M. T.、 ADEJARE A.、 SHAMS G.、 FELLER D. R.、 MILLER D. D.

  DOI：——

  日期：——