Quantitative structure-activity relationships of nicotine analogues as neuronal nicotinic acetylcholine receptor ligands

Bioorg Med Chem. 1996 Dec;4(12):2211-7. doi: 10.1016/s0968-0896(96)00233-7.

Abstract

Quantitative structure-activity relationships of 34 pyrrolidine-modified nicotine agonists are investigated for their binding affinity toward neuronal nicotinic acetylcholine receptor. The results indicate that a large substituent at the R1, R2, and R3 position is detrimental to the binding affinity. Likewise, a large substituent at the R2 alpha or R3 alpha position as well as a hydrogen bond accepting substituent at the R2 beta position are not beneficial to the binding.

MeSH terms

  • Binding Sites
  • Hydrogen Bonding
  • Models, Biological
  • Models, Molecular
  • Nicotine / analogs & derivatives*
  • Nicotine / chemistry*
  • Nicotine / metabolism
  • Receptors, Nicotinic / chemistry
  • Receptors, Nicotinic / metabolism*
  • Regression Analysis
  • Structure-Activity Relationship

Substances

  • Receptors, Nicotinic
  • Nicotine