Studies on Antispasmodics. IV. Synthesis and Anticholinergic Activity of Diarylhydroxymethylquinolizidine Methohalides

Abstract

1-, 2-, and 3-Diarylhydroxymethylquinolizidine methohalides (4-8) were synthesized by quaternization of the corresponding tertiary amines (9-13) in order to develop new antispasmodics. Complete stereoselectivity was observed in the quaternization of the amines (9-13). The stereochemistry of these methohalides was confirmed by the chemical shift of N⁺-methyl signals in the ¹H- and ¹³C-nuclear magnetic resonance spectra. Some of these methohalides exhibited potent anticholinergic activities. Some structure-activity relationships are also discussed.