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Synthesis, structural and conformational study of some esters derived from 3-methyl-3-azabicyclo[3.2.1]octan-8(α and β)-ols

AutorIriepa, I.; Bellanato, Juana
Palabras claveBicyclic α- and β-esters
3-Methyl-3-azabicyclo[3.2.1]octan-8α(and β)-ols
NMR spectroscopy
Conformational analysis
Analgesic and antipyretic activities
Fecha de publicación16-may-2014
CitaciónJournal of Molecular Structure 1073: 31- 36 (2015)
Resumen© 2014 Elsevier B.V. All rights reserved. Abstract A series of α and β-esters bearing a 3-methyl-3-azabicyclo[3.2.1]octane moiety as well as methyl and aryl substituents were synthesized and studied by 1H and 13C NMR spectroscopies. In CDCl3 solution, at room temperature, a chair-envelope conformation for the bicycle moiety with the N-CH3 group in equatorial position with respect to the chair ring is proposed for both, α and β-esters. The chair conformation of the piperidine ring is puckered at C8 in the α-epimers and it is flattened at N3, in the β-epimers. Free rotation of the acyloxy group around the C8O bond has also been deduced. Analgesic activity of four of these substances was studied. 8β-Benzoyloxy-3-methyl-3-azabicyclo[3.2.1]octane demonstrated significant analgesic activity in the hot plate test compared to morphine. By measuring the rectal temperature in mice, results also showed a significant antipyretic activity of this compound.
Descripción6 pags.; 1 sch.; 4 tabs.
Versión del editorhttp://dx.doi.org/10.1016/j.molstruc.2014.05.022
Identificadoresdoi: 10.1016/j.molstruc.2014.05.022
issn: 0022-2860
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