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Paper | Regular issue | Vol 53, No. 11, 2000, pp.2403-2413
Published online, 1st January, 1970
DOI: 10.3987/COM-00-8995
Structural and Conformational Studies of 3,8-Diazabicyclo[3.2.1]octane Derivatives, Selective Agonists of μ-Opioid Receptors

Roberto Artali, Daniela Barlocco, Gabriella Bombieri,* Giorgio Cignarella,* and Fiorella Meneghetti

*Istituto di Chimica Farmaceutica e Tossicologica, Università di Milano, Viale Abruzzi, 42, 20131-I Milano, Italy


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 m-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.