[Synthesis of homochiral 5,9-epoxybenzocyclooctenes with amino substitutents: relationship between structure and CNS activity].
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.
Wünsch
B
B
Institut für Pharmazie, Universität München.
Zott
M
M
Höfner
G
G
D000700:Analgesics / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D001522:Behavior, Animal / Q000187:drug effects; D002491:Central Nervous System Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D006993:Hypnotics and Sedatives / Q000138:chemical synthesis / Q000494:pharmacology; D051379:Mice; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000700:Analgesics; D002491:Central Nervous System Agents; D006993:Hypnotics and Sedatives; D011083:Polycyclic Compounds
Synthese homochiraler 5,9-Epoxybenzocyclooctene mit Aminsubstituenten: Zusammenhang zwischen Struktur und ZNS-Aktivität.