The potent cholinergic agonist (i)-cis-2-methyl-5-[(dimethylamino)methyl]-1,3-oxathiolamnee thiodide [ (+l] wasresolved into enantiomeric forms. Their absolute configurations were established by a synthetic pathway that alsoallowed the synthesis of the corresponding diastereomeric (+)- and (-)-trans-2-methyl-5-[(dimethylamino)-methyl]-l,3-oxathiolane methiodide [(+)- and (-)-lo]. Compound (+)-lw, hich is the most potent of the four isomers,showed the same absolute configuration as L-(+)-muscarine and (+)-cis-dioxolane. The four isomers were testedon guinea pig ileum and frog rectus abdominis, and their muscarinic and nicotinic potency (EPMR) and selectivitywere determined. The relationships between stereoisomerism and potency are discussed.

Resolution, Absolute Configuration and Cholinergic Enantioselectivity of (+) and (-) cis-2-Methyl-5-dimethylaminomethyl-1,3-oxathiolane Methiodide / Teodori, E.; Gualtieri, F.; Angeli, P.; Brasili, Livio; Giannella, M. PIGINI M.. - In: JOURNAL OF MEDICINAL CHEMISTRY. - ISSN 0022-2623. - STAMPA. - 29:(1986), pp. 1610-1615.

Resolution, Absolute Configuration and Cholinergic Enantioselectivity of (+) and (-) cis-2-Methyl-5-dimethylaminomethyl-1,3-oxathiolane Methiodide.

BRASILI, Livio;
1986

Abstract

The potent cholinergic agonist (i)-cis-2-methyl-5-[(dimethylamino)methyl]-1,3-oxathiolamnee thiodide [ (+l] wasresolved into enantiomeric forms. Their absolute configurations were established by a synthetic pathway that alsoallowed the synthesis of the corresponding diastereomeric (+)- and (-)-trans-2-methyl-5-[(dimethylamino)-methyl]-l,3-oxathiolane methiodide [(+)- and (-)-lo]. Compound (+)-lw, hich is the most potent of the four isomers,showed the same absolute configuration as L-(+)-muscarine and (+)-cis-dioxolane. The four isomers were testedon guinea pig ileum and frog rectus abdominis, and their muscarinic and nicotinic potency (EPMR) and selectivitywere determined. The relationships between stereoisomerism and potency are discussed.
29
1610
1615
Resolution, Absolute Configuration and Cholinergic Enantioselectivity of (+) and (-) cis-2-Methyl-5-dimethylaminomethyl-1,3-oxathiolane Methiodide / Teodori, E.; Gualtieri, F.; Angeli, P.; Brasili, Livio; Giannella, M. PIGINI M.. - In: JOURNAL OF MEDICINAL CHEMISTRY. - ISSN 0022-2623. - STAMPA. - 29:(1986), pp. 1610-1615.
Teodori, E.; Gualtieri, F.; Angeli, P.; Brasili, Livio; Giannella, M. PIGINI M.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11380/449050
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