Synthesis and structure–Activity data of some new epibatidine analogues Original Research Article

The high-pressure Diels–Alder reaction of N-carbomethoxypyrroles and phenyl vinyl sulfone affords versatile intermediates for the palladium-catalyzed preparation of new epibatidine analogues. Structure–activity relationships of new epibatidine analogues are presented. High affinities of Ki=0.81 and 2.6 nM for the [3H]-cytisine rat brain nicotinic acetylcholine binding sites were found for the 5-pyrimidinyl and the 5-(2-amino)-pyrimidinyl epibatidine analogues, respectively.