Synthesis and pharmacological activity of 2,3,4,5-tetrahydro-1,5-methano-1H-3-benzazepines

2,3,4,5-Tetrahydro-1,5-methano-1H-3benzazepine (4) has been synthesized from 2,3-dioxobenzonorbornene. Oxidative cleavage of the diketone to cis-1,3-indandicarboxylic acid, followed by closure to the corresponding amhydride, conversion to the imide, and lithium aluminum hydride reduction, gave 4. Co...

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Veröffentlicht in:	Journal of medicinal chemistry 1979-04, Vol.22 (4), p.455-457
Hauptverfasser:	Mazzocchi, Paul H, Stahly, Barbara C
Format:	Artikel
Sprache:	eng
Schlagworte:	Analgesics - chemical synthesis Animals Benzazepines - chemical synthesis Benzazepines - pharmacology Mice Morphine - antagonists & inhibitors Reaction Time - drug effects Structure-Activity Relationship
Online-Zugang:	Volltext
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Zusammenfassung:	2,3,4,5-Tetrahydro-1,5-methano-1H-3benzazepine (4) has been synthesized from 2,3-dioxobenzonorbornene. Oxidative cleavage of the diketone to cis-1,3-indandicarboxylic acid, followed by closure to the corresponding amhydride, conversion to the imide, and lithium aluminum hydride reduction, gave 4. Compound 4 and its N-derivatives show no analgesic activity in the mouse hot-plate assay and little antagonist activity in a tail-flick assay.
ISSN:	0022-2623 1520-4804
DOI:	10.1021/jm00190a020