[Structure and conformation-activity relationships of cyclic acetylcholine analogues / 12th communication: Synthesis and cholinergic properties of stereoisomeric 3-acetoxythiacyclohexanes (author's transl)].
In the course of investigations of structure and conformation-activity relationships of cyclic acetylcholine analogues, both the enantiomers of trans-3-acetoxy-1-methylthioniacyclohexane were prepared. These two esters and the corresponding racemate of the cis-ester were tested for nicotine- and muscarine-like activity. The stereoisomeric cyclic analogues differ substantially in pharmacological activity. The cis-sulfonium ester shows the highest nicotinic potency (1/25 the nicotinic potency of acetylcholine), and the (+)-trans-ester has no agonistic properties when tested at nicotinic receptors, but it shows the highest muscarinic potency in this series.
D000109:Acetylcholine / Q000031:analogs & derivatives* / Q000494:pharmacology; D000818:Animals; D001794:Blood Pressure / Q000187:drug effects; D055598:Chemical Phenomena; D002621:Chemistry; D003510:Cyclohexanes / Q000494:pharmacology*; D003512:Cyclohexanones / Q000494:pharmacology*; D006168:Guinea Pigs; D066298:In Vitro Techniques; D008968:Molecular Conformation; D009119:Muscle Contraction / Q000187:drug effects; D011896:Rana temporaria; D051381:Rats; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D003510:Cyclohexanes; D003512:Cyclohexanones; D000109:Acetylcholine
Struktur-und Konformations-Wirkungs-Beziehungen heteroxyklischer Acetylcholin-analoga. 12. Mitteilung: Synthese und cholinerge Eigenschaften stereoisomerer 3-Acetoxythiacyclohexame).