title: [Structural study of substituted benzamides with antidopaminergic D-2 activity. Comparison with orthopramides with 5HT-3 antiserotoninergic profile].
abstract: Crystallographic results coupled with theoretical calculations, NMR analyses, and molecular graphic design have been used to investigate the three-dimensional structures of different Na(+)-dependent D-2 antagonists. Three putative pharmacophoric elements, a nitrogen lone pair, a phenyl ring, and a carbonyl moiety, are similarly oriented in all these compounds. Moreover, a stereoelectronic model can be deducted from the molecular electrostatic potential maps. Conversely, for Na(+)-independent analogs, the two latter pharmacophoric elements play a subordinate role, but two electron regions are systematically localized on the other side of the molecule. The three pharmacophoric elements of the Na(+)-dependent D-2 antagonists have been identified in the 5HT-3 antiserotoninergic drugs, but only in terms of chemical functions.
authors.affiliation: Laboratoire de Chimie Moléculaire Structurale, Facultés Universitaires Notre-Dame de la Paix, Namur, Belgique.
authors.forename: S
authors.initials: S
authors.lastname: Collin
mesh_terms: D001549:Benzamides / Q000138:chemical synthesis* / Q000494:pharmacology; D003460:Crystallization; D018492:Dopamine Antagonists; D015195:Drug Design; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D017448:Receptors, Dopamine D2; D012702:Serotonin Antagonists / Q000494:pharmacology*
chemical_list: D001549:Benzamides; D018492:Dopamine Antagonists; D017448:Receptors, Dopamine D2; D012702:Serotonin Antagonists
vernacular_title: Etude structurale de benzamides substitués à activité antidopaminergique D-2. Comparison avec des orthopramides au profil antiserotonrgique 5HT-3.