Synthesis and pharmacological evaluation of novel 9- and 10-substituted cytisine derivatives. Nicotinic ligands of enhanced subtype selectivity

J Med Chem. 2006 May 4;49(9):2673-6. doi: 10.1021/jm051196m.

Abstract

We report the synthesis and pharmacological properties of several cytisine derivatives. Among them, two 10-substituted derivatives showed much higher selectivities for the alpha4beta2 nAChR subtype in binding assays than cytisine. The 9-vinyl derivative was found to have a very similar agonist activity profile to that of cytisine.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkaloids / chemical synthesis
  • Alkaloids / chemistry*
  • Alkaloids / pharmacology*
  • Azocines / chemical synthesis
  • Azocines / chemistry
  • Azocines / pharmacology
  • Cholinergic Agonists / chemical synthesis
  • Cholinergic Agonists / chemistry
  • Cholinergic Agonists / pharmacology
  • Hydrophobic and Hydrophilic Interactions
  • Ligands
  • Molecular Structure
  • Nicotine / chemical synthesis
  • Nicotine / chemistry*
  • Nicotine / classification
  • Nicotine / pharmacology*
  • Quinolizines / chemical synthesis
  • Quinolizines / chemistry
  • Quinolizines / pharmacology
  • Receptors, Cholinergic / metabolism

Substances

  • Alkaloids
  • Azocines
  • Cholinergic Agonists
  • Ligands
  • Quinolizines
  • Receptors, Cholinergic
  • cytisine
  • Nicotine