Synthesis of homochiral 5,9-epoxybenzocyclooctenes with aminosubstituents: Relationship between structure and CNS-activity

Article abstract of DOI:10.1002/ardp.19933261011

This paper deals with the synthesis and psychopharmacological effects of variations of the sedative and analgesic tricyclic amines 3a and 3b: Starting with the homochiral ketone 4 the amines 5 (primary amino group in equatorial position), 7 (axially oriented dimethylamino group), 9 (additional phenyl residue in position 7), 13b, and 14b (equatorially and axially arranged dimethylaminomethyl group) and 23 and 24 (axial amino group shifted to position 9) are prepared. BBr₃ cleaves the phenolic ethers of the secondary amine (±)-3a to yield the aminodiphenol (±)-10. - Keeping mice under observation for behavioral anomalies (Irwin screen) and analgesic activity (writhing test) shows, that the amines 5, 7, 9, (±)-10, 13b, 14b, and 23 do not reach the sedative and analgesic effects of the amines 3a and 3b, described by us.