6533b7d5fe1ef96bd1263cba
RESEARCH PRODUCT
Muscarinic Properties of Compounds Related to Arecaidine Propargyl Ester
Ulrich MoserGerd DannhardtErnst MutschlerCaren HildebrandtGünter LambrechtVincenzo TumiattiJahn Wehrlesubject
MaleDouble bondStereochemistryArecolineGuinea PigsCholinergic AgentsIn Vitro Techniqueschemistry.chemical_compoundVas DeferensIleumDrug DiscoveryMuscarinic acetylcholine receptorAnimalsMoietySingle bondReceptorReceptor Muscarinic M3chemistry.chemical_classificationReceptor Muscarinic M2Receptor Muscarinic M1HeartMuscle SmoothArecaidineTriple bondMyocardial ContractionReceptors MuscarinicchemistryPropargylFemaleRabbitsMuscle Contractiondescription
A series of new analogues of the arecaidine propargyl ester (CAS 35516-99-5, APE, 1a) with alcohols consisting of 4 or 5 carbon atoms were investigated at muscarinic receptor subtypes. The muscarinic activity of the quaternary and tertiary salts of the APE-related compounds were assayed on the isolated guinea-pig ileum (M 3 receptor subtype) and guinea-pig left atria (M 2 receptor subtype) as well as on rabbit isolated vas deferens (M 1 receptor subtype). The structural variations made in the APE molecule, replacing the triple bond in the ester side chain with structures such as double bond, an allene moiety, a single bond, a cyclopropyl group or two triple bonds should alter the selectivity and potency in favour of the M 2 subtype. Enhanced, though modest, selectivity for M 2 receptors was achieved with the 2-butynyl ester 2a. The other structural variations resulted in a loss of potency, but not necessarily of efficacy.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2011-12-28 | Arzneimittelforschung |