A series of 1,3-dioxolane-based ligands, bearing hydroxymethyl or ester functionalities, was synthesized and tested as potential muscarinic antagonists. The compounds display moderate to low affinity for the three receptor subtypes M(1)-M(3), with some of them showing a significant selectivity for the M(3) subtype. The configurational and conformational properties were studied using NOE experiments and vicinal coupling constants. The LH and C-13 NMR chemical shifts show stereochemically dependent trends. Quantitative analysis of conformer populations showed that the exocyclic CH2N+(CH3)(3) group is prevalently in a pseudo-axial orientation in the cis isomers and in a pseudo-equatorial orientation in the trans isomers. Copyright

Synthesis, NMR spectroscopy study, and antimuscarinic activity of a series of 2-(acyloxymethyl)-1,3-dioxolanes / L., Malmusi; Mucci, Adele; Schenetti, Luisa; U., Gulini; G., Marucci; Brasili, Livio. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 0968-0896. - STAMPA. - 4:(1996), pp. 2071-2080.

Synthesis, NMR spectroscopy study, and antimuscarinic activity of a series of 2-(acyloxymethyl)-1,3-dioxolanes

MUCCI, Adele;SCHENETTI, Luisa;BRASILI, Livio
1996

Abstract

A series of 1,3-dioxolane-based ligands, bearing hydroxymethyl or ester functionalities, was synthesized and tested as potential muscarinic antagonists. The compounds display moderate to low affinity for the three receptor subtypes M(1)-M(3), with some of them showing a significant selectivity for the M(3) subtype. The configurational and conformational properties were studied using NOE experiments and vicinal coupling constants. The LH and C-13 NMR chemical shifts show stereochemically dependent trends. Quantitative analysis of conformer populations showed that the exocyclic CH2N+(CH3)(3) group is prevalently in a pseudo-axial orientation in the cis isomers and in a pseudo-equatorial orientation in the trans isomers. Copyright
1996
4
2071
2080
Synthesis, NMR spectroscopy study, and antimuscarinic activity of a series of 2-(acyloxymethyl)-1,3-dioxolanes / L., Malmusi; Mucci, Adele; Schenetti, Luisa; U., Gulini; G., Marucci; Brasili, Livio. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 0968-0896. - STAMPA. - 4:(1996), pp. 2071-2080.
L., Malmusi; Mucci, Adele; Schenetti, Luisa; U., Gulini; G., Marucci; Brasili, Livio
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/306326
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