title: Synthesis and structure-activity data of some new epibatidine analogues.
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.
authors.affiliation: Department of Organic Chemistry, NSR Center for Molecular Structure, Design, and Synthesis, University of Nijmegen, The Netherlands. J.P.G.Seerden@chem.rug.nl
authors.forename: J P
authors.initials: JP
authors.lastname: Seerden
authors.forename: M T
authors.initials: MT
authors.lastname: Tulp
authors.forename: H W
authors.initials: HW
authors.lastname: Scheeren
authors.forename: C G
authors.initials: CG
authors.lastname: Kruse
mesh_terms: D000470:Alkaloids / Q000378:metabolism; D000818:Animals; D001392:Azocines; D001667:Binding, Competitive; D001921:Brain / Q000378:metabolism; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D002462:Cell Membrane / Q000378:metabolism; D015195:Drug Design; D007202:Indicators and Reagents; D007700:Kinetics; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D018722:Nicotinic Agonists / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D011807:Quinolizines; D051381:Rats; D011978:Receptors, Nicotinic / Q000187:drug effects / Q000378:metabolism*; D013329:Structure-Activity Relationship; D000093843:Quinolizidine Alkaloids
chemical_list: D000470:Alkaloids; D001392:Azocines; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007202:Indicators and Reagents; D018722:Nicotinic Agonists; D011725:Pyridines; D011807:Quinolizines; D011978:Receptors, Nicotinic; C004712:cytisine; D000093843:Quinolizidine Alkaloids; C082748:epibatidine