Summary
Replacing the tetrahydrofuran ring in muscarine by tetrahydrothiophene results in a markedly reduced biological activity. This may be explained by the inability of the sulfur atom to form hydrogen bonds with the cholinergic receptor group. The increase in ring size also affects the position and biological function of the neighbouring methyl group. Aromaticity of the furan ring has little effect on biological activity of muscarine, in contrast to the striking decrease which occurs when methyl or trimethylammonium groups are incis-position with respect to the hydroxy-group.
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Waser, P.G. Struktur und Wirkung von muscarinähnlichen Verbindungen. Experientia 16, 347–349 (1960). https://doi.org/10.1007/BF02157893
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DOI: https://doi.org/10.1007/BF02157893