European Journal of Medicinal Chemistry p. 231 - 240 (1997)
Update date:2022-07-30
Topics:
Macchia, B.
Macchia, M.
Martinelli, A.
Martinotti, E.
Orlandini, E.
et al.
Previous drug-receptor interaction mechanism studies at the molecular level of adrenergic drugs made it possible to construct two three-dimensional molecular models, A and B, using conformationally restrained cyclic analogues of natural catecholamines, including 3-(3,4-dihydroxyphenyl)-3-piperidinol (3-DPP, 3); these models offer useful information about the steric requirements for the direct activation of α1- and α2-adrenergic receptors, respectively.In order to gain further knowledge about the steric requirements of these receptors, we also synthesized 3-(3,4-dihydroxyphenyl)-c-2-methyl-r-3-piperidinol (2-MDPP, 8) and the 3-(3,4-dihydroxyphenyl)-c- and -t-6-methyl-r-3-piperidinols (6-MDPPs 9 and 10); these differ from the 3-DPP 3 used for the construction of the molecular models exclusively in the presence of a methyl in the 2 or 6 position of the heterocyclic ring.The configuration and conformation of the MDPPs 8-10 were assigned by 1H-NMR and IR studies, and confirmed by conformational analysis performed by means of theoretical calculations.The α1- and α2-adrenergic properties were evaluated in vitro both by radioligand binding assays and by functional tests on isolated preparations.The results obtained made it possible to obtain a more refined steric definition of the A and B models. - Keywords: 3-piperidinol derivative; adrenergic α-stimulating activity; conformational analysis; molecular model.
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