title: Synthesis and pharmacological activity of 2,3,4,5,-tetrahydro-1,5-methano-1H-3-benzazepines.
abstract: 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.
mesh_terms: D000700:Analgesics / Q000138:chemical synthesis*; D000818:Animals; D001552:Benzazepines / Q000138:chemical synthesis* / Q000494:pharmacology; D051379:Mice; D009020:Morphine / Q000037:antagonists & inhibitors; D011930:Reaction Time / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000700:Analgesics; D001552:Benzazepines; D009020:Morphine