I. Iriepa, J. Bellanato, E. Gálvez
Jul 15, 2010
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0
Influential Citations
4
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Journal
Journal of Molecular Structure
Abstract
Abstract Some mono-substituted amides ( 2 – 5 ) derived from 3-methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9α-amine were synthesized and studied by IR, 1 H and 13 C NMR spectroscopy. The crystal structure of 3-methyl-2,4-diphenyl-9α-(3,5-dichlorobenzamido)-3-azabicyclo[3.3.1]nonane ( 3 ) was determined by X-ray diffraction. NMR data showed that all compounds adopt in CDCl 3 a preferred flattened chair–chair conformation with the N -CH 3 group in equatorial disposition. X-ray data agreed with this conformation in the case of compound 3 . IR data revealed that compounds 2 and 3 present a C O⋯HN intermolecular bond in the solid state. This conclusion was also confirmed by X-ray data of compound 3 . In the case of compound 5 , IR results suggested intermolecular NH⋯N-heterocyclic bonding. On the contrary, in the pyrazine derivative ( 4 ), IR, 1 H and 13 C NMR data showed the presence of an intramolecular NH⋯N1″-heterocyclic hydrogen bond in the solid state and solution. Moreover, NMR and IR data showed a preferred trans disposition for the NH–C O group. NMR also revealed free rotation of the –NH–CO–R group around C9–NH bond. Pharmacological assays on mice were drawn to evaluate analgesic activity.