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

Authors
Artali, R Barlocco, D Bombieri, G Cignarella, G Meneghetti, F
Citation
R. Artali et al., Structural and conformational studies of 3,8-diazabicyclo[3.2.1]octane derivatives, selective agonists of mu-opioid receptors, HETEROCYCLE, 53(11), 2000, pp. 2403
Citations number
12
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
53
Issue
11
Year of publication
2000
Database
ISI
SICI code
0385-5414(20001101)53:11<2403:SACSO3>2.0.ZU;2-X
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 mu -opioid receptors. The conformatio ns are compared with morphine, chosen for its mu -affinity and structural r igidity. The X-Ray crystal and molecular structures of 3-p-nitrocinnamyl-8- propionyl-3,8-diazabicyclo[3.2.1]octane (Ib) and of two higher homologs 8-n -butyroyl- (1c) and pivaloyl- (1d) have been compared with the theoretical results.