Novel 4-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)methylbenzofuran derivatives as selective alpha(2C)-adrenergic receptor antagonists

Bioorg Med Chem Lett. 2007 Mar 15;17(6):1616-21. doi: 10.1016/j.bmcl.2006.12.094. Epub 2007 Jan 25.

Abstract

The synthesis of a series of 4-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)methyl-2-arylbenzofuran and 4-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)methylbenzofuran-2-carboxamide derivatives as novel alpha(2C)-adrenergic receptor antagonists are described. Their affinity at three different human alpha(2)-adrenergic receptors is reported, and some of these compounds exhibited high affinity for the alpha(2C)-adrenergic receptor with high subtype selectivity. Among them, compound 10e has been found to show the anti-L-dopa-induced dyskinetic activity in marmosets. The structure-activity relationship of these compounds is also discussed.

MeSH terms

  • Adrenergic alpha-2 Receptor Antagonists*
  • Adrenergic alpha-Antagonists / chemical synthesis*
  • Adrenergic alpha-Antagonists / pharmacology*
  • Animals
  • Benzofurans / chemical synthesis*
  • Benzofurans / pharmacology*
  • Callithrix
  • Dopamine Agents / pharmacology
  • Dyskinesia, Drug-Induced / physiopathology
  • Humans
  • Indicators and Reagents
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / pharmacology*
  • Levodopa / antagonists & inhibitors
  • Levodopa / pharmacology
  • Receptors, Adrenergic, alpha-2
  • Structure-Activity Relationship

Substances

  • 4-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)methylbenzofuran
  • ADRA2C protein, human
  • Adrenergic alpha-2 Receptor Antagonists
  • Adrenergic alpha-Antagonists
  • Benzofurans
  • Dopamine Agents
  • Indicators and Reagents
  • Isoquinolines
  • Receptors, Adrenergic, alpha-2
  • Levodopa