Paper Report for: Eberlein_1988_J.Med.Chem_31_1169
Reference
Title: Tricyclic compounds as selective antimuscarinics. 2. Structure-activity relationships of M1-selective antimuscarinics related to pirenzepine Eberlein WG, Engel WW, Trummlitz G, Schmidt G, Hammer R Ref: Journal of Medicinal Chemistry, 31:1169, 1988 : PubMed
In order to gain some insight into those structural features that control M1 selectivity, a selected set of pirenzepine analogues has been studied in which both the tricyclic ring system and the basic side chain have been varied. Binding studies were conducted in rat tissue homogenates from cerebral cortex (M1) and gastric fundus (M2). The ratio of IC50 values of the test compounds in the two different tissues was taken as a measure of M1 receptor selectivity. Several derivatives, especially those with flexible side chains, i.e. high degree of freedom of rotation around single bonds, proved to be nonselective. Among semirigid compounds only those containing 6-membered ring systems (11, 13, 14, and 15) showed significant M1 selectivity. Principles of structure-activity and structure-selectivity are discussed.
        
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Eberlein WG, Engel WW, Trummlitz G, Schmidt G, Hammer R (1988) Tricyclic compounds as selective antimuscarinics. 2. Structure-activity relationships of M1-selective antimuscarinics related to pirenzepine Journal of Medicinal Chemistry31: 1169-74
Eberlein WG, Engel WW, Trummlitz G, Schmidt G, Hammer R (1988) Journal of Medicinal Chemistry31: 1169-74