1251920-18-9Relevant academic research and scientific papers
Synthesis, structural, conformational and pharmacological study of some amides derived from 3-methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9α-amine
Iriepa,Bellanato,Gálvez,Gil-Alberdi
, p. 190 - 195 (2010)
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, 1H and 13C 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 CDCl3 a preferred flattened chair-chair conformation with the N-CH3 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{double bond, long}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, 1H and 13C 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{double bond, long}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.
