Quantum mechanic calculations have been done on a set of 3,8-diazabicyclo[3.2.1]octane derivatives in order to elucidate their electronic structure in relation to the affinity towards the μ-opioid receptors. The conformations are compared with morphine, chosen for its μ-affinity and structural rigidity. The X-Ray crystal and molecular structures of 3-p-nitrocinnamyl-8-propionyl-3,8-diazabicyclo[3.2.1]octane (1b) and of two higher homologs 8-n-butyroyl- (1c) and pivaloyl- (1d) have been compared with the theoretical results.

Structural and conformational studies of 3,8-diazabyciclo[3.2.1]octane derivatives, selective agonists of µ-opioid receptors / R. Artali, D. Barlocco, G. Bombieri, G. Cignarella, F. Meneghetti. - In: HETEROCYCLES. - ISSN 0385-5414. - 53:11(2000), pp. 2403-2413. [10.3987/COM-00-8995]

Structural and conformational studies of 3,8-diazabyciclo[3.2.1]octane derivatives, selective agonists of µ-opioid receptors

R. Artali
Primo
;
D. Barlocco
Secondo
;
G. Bombieri;G. Cignarella
Penultimo
;
F. Meneghetti
Ultimo
2000

Abstract

Quantum mechanic calculations have been done on a set of 3,8-diazabicyclo[3.2.1]octane derivatives in order to elucidate their electronic structure in relation to the affinity towards the μ-opioid receptors. The conformations are compared with morphine, chosen for its μ-affinity and structural rigidity. The X-Ray crystal and molecular structures of 3-p-nitrocinnamyl-8-propionyl-3,8-diazabicyclo[3.2.1]octane (1b) and of two higher homologs 8-n-butyroyl- (1c) and pivaloyl- (1d) have been compared with the theoretical results.
Settore CHIM/08 - Chimica Farmaceutica
2000
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/66089
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