Details

Autor(en) / Beteiligte

• Mavromoustakos, T
• Yang, DP
• Theodoropoulou, E
• Makriyannis, A

Titel

Studies of the conformational properties of the cannabimimetic aminoalkylindole pravadoline using NMR and molecular modeling

Ist Teil von

• European journal of medicinal chemistry, 1995, Vol.30 (3), p.227-234

Ort / Verlag

Oxford: Elsevier Masson SAS

Erscheinungsjahr

1995

Quelle

Elsevier Journal Backfiles on ScienceDirect (DFG Nationallizenzen)

Beschreibungen/Notizen

• The conformation of the cannabimimetic aminoalkylindole (AAI) pravadoline was studied using a combination of 2D-NMR techniques and computational molecular modeling. This conformation of pravadoline was then compared with that of the analgesic nonclassical cannabinoid (NCC) CP-55940. The pair of more potent and more conformationally restrained analogs WIN 55212-2 and CP-55944 were also included in the comparison study. The results showed that the apparent structural dissimilarities between the AAIs and the NCCs can be reconciled when a closer examination of their preferred conformations is undertaken. Such a study revealed that there is a good correspondence between their respective pharmacophoric groups when the molecules are properly superimposed. Furthermore, the polar and nonpolar groups that determine their amphipathic properties are arranged on the same side of each of these four molecules.