Coaxing a Pyridine Nucleus To Give Up Its Aromaticity: Synthesis and Pharmacological Characterization of Novel Conformationally Restricted Analogues of Nicotine …
A series of novel nicotine and anabasine related conformationally restricted compounds including those with π-bonds in the connecting tether were synthesized following the hitherto unprecedented phenylsulfanyl group assisted generation of pyridine o- quinodimethane intermediates and their trapping by an intramolecular Diels-Alder reaction. Pharmacological characterization of some of these analogues at activating α3β4 nAChRs ...