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Synthesis and structure-activity data of some new epibatidine analogues
J P Seerden1, M T Tulp, H W Scheeren
1Department of Organic Chemistry, NSR Center for Molecular Structure, Design, and Synthesis, University of Nijmegen, The Netherlands. J.P.G.Seerden@chem.rug.nl
Bioorganic & Medicinal Chemistry
|January 9, 1999
Abstract:
The high-pressure Diels-Alder reaction of N-carbomethyoxypyrroles 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.