2,3,4,4a,5,9b-Hexahydro-1H-indeno[1,2-b]pyridines: potential antidepressants

The synthesis of various diastereoisomeric H4a,H5-cis,H4a,H9b-cis- and H4a,H5-trans,H4a,H9b-cis-2,3,4,4a,5,9b-hexahydro -1H-indeno[1,2-b]pyridines is described, as well as the evaluation of their antidepressant potency. Elucidation of structure-activity relationships revealed the H4a,H5-trans compou...

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Veröffentlicht in:	Journal of medicinal chemistry 1984-04, Vol.27 (4), p.432-439
Hauptverfasser:	Kunstmann, Rudolf, Lerch, Ulrich, Gerhards, Hermann, Leven, Margret, Schacht, Ulrich
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Antidepressive Agents - chemical synthesis Biogenic Amines - metabolism Biological Transport - drug effects Blepharoptosis - drug therapy Brain - metabolism Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Indenes - chemical synthesis Indenes - pharmacology Indenes - therapeutic use Indicators and Reagents Kinetics Mice Motor Activity - drug effects Organic chemistry Preparations and properties Pyridines - chemical synthesis Pyridines - pharmacology Pyridines - therapeutic use Rats Structure-Activity Relationship Synaptosomes - drug effects Synaptosomes - metabolism Tetrabenazine - toxicity
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Zusammenfassung:	The synthesis of various diastereoisomeric H4a,H5-cis,H4a,H9b-cis- and H4a,H5-trans,H4a,H9b-cis-2,3,4,4a,5,9b-hexahydro -1H-indeno[1,2-b]pyridines is described, as well as the evaluation of their antidepressant potency. Elucidation of structure-activity relationships revealed the H4a,H5-trans compounds as being by far the more active of the two series of diastereoisomers. Pharmacological and biochemical data suggest that these compounds are potential antidepressants with central stimulating properties, which are characterized by strong norepinephrine and dopamine reuptake inhibition.
ISSN:	0022-2623 1520-4804
DOI:	10.1021/jm00370a004