Abstract
A new approach has been proposed for simplification of the morphine molecule in order to obtain new potential μ- and δ-opiate receptor ligands. The reaction of 1,2,5-trimethyl-4-piperidone and 2,2-di-methyl-4-tetrahydropyrone with substituted benzalacetones under Robinson ring fusion conditions gave decahydroisoquinoline and decahydroisochromene derivatives. A thorough conformational analysis of these products was carried out. The effect of the products on the functional activity of opiate receptors on the mouse vas deferens isolated organ (MVD) model was studied. Prior screening showed that 8-(p-dimethylaminophenyl)-4a-hydroxy-2,3,8a-trimethyldecahydro-6-isoquinolone displays opiate activity and has agonist properties.
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