10-Hydroxy-4-methyl-2,3,4,5,6,7-hexahydro-1,6-methano-1H-4-benzazonine derivatives (homobenzomorphans) as analgesics.
Six 10-hydroxy-4-methyl-2,3,4,5,6,7-hexahydro-1,6-methano-1H-4-benzazonine derivatives 17a-f have been synthesized as potential analgesics. The synthesis of these compounds involved conversion of 4-(2-dimethylaminoethyl)-6-methoxy alpha tetralone derivatives 12a-f to their N-methyl analogues and the subsequent intramolecular mannich reaction with formaldehyde to give the 7-keto C-ring homobenzomorphans 14a-f from which 17a-f, respectively, were obtained. Compounds 17a-f are as potent as morphine as analgesics (mice).
D000701:Analgesics, Opioid / Q000138:chemical synthesis*; D000818:Animals; D001575:Benzomorphans / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D003061:Codeine / Q000494:pharmacology; D007928:Lethal Dose 50; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D009019:Morphinans / Q000138:chemical synthesis*; D009020:Morphine / Q000494:pharmacology; D011930:Reaction Time / Q000187:drug effects; D013329:Structure-Activity Relationship
D000701:Analgesics, Opioid; D001575:Benzomorphans; D009019:Morphinans; D009020:Morphine; D003061:Codeine