Relation between structure and cholinergic activity. I. Synthesis and muscarinic activity of 5‐alkyl‐2‐methyl‐4‐trimethylammoniomethyl‐1,3‐dioxolane iodides
- 1 January 1972
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 91 (8) , 989-1001
- https://doi.org/10.1002/recl.19720910813
Abstract
The preparation and muscarinic activities of a number of 5‐alkyl substituted analogues of the dioxolane of Fourneau are described. Muscarinic activity decreases rapidly when the alkyl chain lengthens, moreover a change from parasympathomimetic into parasympatholytic activity occurs. The stereochemical aspects with regard to the 5‐position are considered. The synthesis and cholinolytic effect of 2‐methyl‐c‐5‐propyl‐r‐4‐trimethylammoniomethyl‐1,3‐dioxolane iodide and the corresponding 4,5‐trans compound are described.Keywords
This publication has 11 references indexed in Scilit:
- Cholinergic receptor. II. Monosubstituted and bicyclic derivatives of cis-2-methyl-4-dimethylaminomethyl-1,3-dioxolane methiodideJournal of Medicinal Chemistry, 1969
- Configurational equilibria in 2,4,5-trisubstituted 1,3-dioxolanesTetrahedron Letters, 1969
- Cholinergic Receptor I. Cholinomimetic Activities of Some Analogs of cis-2-Methyl-4-dimethylaminomethyl-1,3-dioxolane MethiodideJournal of Pharmaceutical Sciences, 1968
- Aspects of stereochemistry. Part XXIII. Configuration of some 2,4-disubstituted derivatives of 1,3-dioxolanJournal of the Chemical Society C: Organic, 1966
- Stereochemistry of the Interaction of Enantiometic 1,3-Dioxolane Analogs of Muscarone with Cholinergic Receptors1Journal of Medicinal Chemistry, 1963
- STUDIES ON THE CHEMICAL BASIS FOR CHOLINOMIMETIC AND CHOLINOLYTIC ACTIVITY: PART I. THE SYNTHESIS AND CONFIGURATION OF QUATERNARY SALTS IN THE 1,3-DIOXOLANE AND OXAZOLINE SERIESCanadian Journal of Chemistry, 1962
- Mikromethode zur Bestimmung der Ringstruktur des Zuckerrestes bei NucleosidenHelvetica Chimica Acta, 1955
- STUDIES ON THE STRUCTURE‐ACTION RELATIONSHIPS OF THE CHOLINE GROUPBritish Journal of Pharmacology and Chemotherapy, 1952
- The Structure-Action Relationships of the Choline GroupScience, 1949