Synthesis of 3,6-diazabicyclo[3.1.1]heptanes as novel ligands for neuronal nicotinic acetylcholine receptors

Bioorg Med Chem Lett. 2008 Dec 1;18(23):6147-50. doi: 10.1016/j.bmcl.2008.10.002. Epub 2008 Oct 5.

Abstract

Alpha series of novel 3,6-diazabicyclo[3.1.1]heptane derivatives 4a-f was synthesized and their affinity and selectivity towards alpha4beta2 and alpha7 nAChR subtypes were evaluated. The results of the current study revealed a number of compounds (4a, 4b and 4c) having a very high affinity for alpha4beta2 (K(i) at alpha4beta2 ranging from 0.023 to 0.056 nM) versus alpha7 nAChR subtypes; among these compounds, the 3-(6-bromopyridin-3-yl)-3,6-diazabicyclo[3.1.1]heptane 4c was found to be the most alpha7alpha4beta2 selective term in receptor binding assays (alpha7alpha4beta2=1295). Moreover, compound 4d also had high affinity for the alpha4beta2 nAChR subtype (K(i)=1.2 nM) with considerably high selectivity (alpha7/alpha4beta2=23300).

MeSH terms

  • Binding Sites
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Bridged Bicyclo Compounds, Heterocyclic / pharmacology*
  • Heptanes / chemical synthesis*
  • Heptanes / chemistry
  • Heptanes / pharmacology*
  • Ligands
  • Molecular Structure
  • Nicotine / metabolism
  • Nicotinic Agonists / chemical synthesis*
  • Nicotinic Agonists / chemistry
  • Nicotinic Agonists / pharmacology*
  • Receptors, Nicotinic / drug effects*
  • Structure-Activity Relationship

Substances

  • 3-(6-bromopyridin-3-yl)-3,6-diazabicyclo(3.1.1)heptane
  • Bridged Bicyclo Compounds, Heterocyclic
  • Heptanes
  • Ligands
  • Nicotinic Agonists
  • Receptors, Nicotinic
  • nicotinic receptor alpha4beta2
  • Nicotine