Enantioselectivity of Muscarinic Antagonists. 2,2-Dicyclohexyl-5-((dimethylamino)methyl)-1,3-oxathiolane Methiodide and Related 3-oxide.

The enantiomers of three chiral muscarinic antagonists carrying a 1,3-oxathiolane nucleus were prepared and theirabsolute configuration established. The enantioselectivity and tissue selectivity of such compounds were studiedon rat bladder and guinea pig ileum and heart. The results show that introduction of a sulfoxide function bringsabout a small but definite enantioselectivity in the 1,3-oxathiolane compound (2), which in itself does not showenantioselectivity among the tissues studied. The results obtained point to differences among cardiac and ilealmuscarinic receptors. Comparison of the absolute configuration related shows that the most potent isomersof both series share the same absolute stereochemistry.