PMID: 7674Jun 1, 1976

10-Hydroxy-4-methyl-2,3,4,5,6,7-hexahydro-1,6-methano-1H-4-benzazonine derivatives (homobenzomorphans) as analgesics

Journal of Medicinal Chemistry
S Shiotani, T Kometani

Abstract

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).

Related Concepts

Opioids
Benzomorphan
Isocodeine
Lethal Dose 50
Morphinans
Morphine Sulfate (2: 1), Pentahydrate
In Vivo NMR Spectroscopy
Reaction Time
Structure-Activity Relationship

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