• Article

Synthesis, nicotinic acetylcholine receptor binding, and antinociceptive properties of 2-exo-2-(2 '-substituted-3 ' phenyl-5 '-pyridinyl)-7-azabicyclo[2.2.1]heptanes. Novel nicotinic antagonist

A series of 2'-substituted-3'-phenyl epibatidine analogues were synthesized and evaluated for inhibition of binding at nicotine acetylcholine receptors and for antinociceptive properties in mice. The introduction of a bulky phenyl group at the T-position exerted a profound influence on both receptor binding and antinociceptive effects. Substitution of different groups at the 2'-position distinguished between agonist and antagonist properties. These results demonstrate that structural requirements for receptor activities and recognition are distinctively different.

Citation

Carroll, F., Lee, J., Navarro, H., Brieaddy, L., Abraham, P., Damaj, M. I., & Martin, B. R. (2001). Synthesis, nicotinic acetylcholine receptor binding, and antinociceptive properties of 2-exo-2-(2 '-substituted-3 ' phenyl-5 '-pyridinyl)-7-azabicyclo[2.2.1]heptanes. Novel nicotinic antagonist. Journal of Medicinal Chemistry, 44(24), 4039-4041.