[CNS-agents: synthesis and properties of 3-anilino-8-oxatropanes].
Reaction of the 8-oxabicyclooctenone and -octanone derivatives 3 and 4 with aniline and metal hydrides yields the 3 alpha-isomers of the aniline derivatives 7 and 8, preferably. The configuration can be determined by NMR-spectroscopy and by cyclization to the scopoline analogue 9b. Depending on the N-substitution the pyran rings of the alpha-isomers are flattened (7,8) or deformed to give a boat conformation (10,11,13). The conformationally restricted aniline derivative 18 can be obtained from 4 with 2-aminobenzaldehyde and diborane, trans-configuration is preferred in 18. Some substrates reveal CNS-effects in mice.
Eiden
F
F
Institut für Pharmazie und Lebensmittelchemie, Ludwig-Maximilians-Universität München.
Kainz
A
A
D000700:Analgesics / Q000138:chemical synthesis / Q000494:pharmacology; D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D002491:Central Nervous System Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D051379:Mice; D011714:Pyrans / Q000138:chemical synthesis* / Q000494:pharmacology; D014326:Tropanes / Q000138:chemical synthesis* / Q000494:pharmacology
D000700:Analgesics; D000814:Aniline Compounds; D002491:Central Nervous System Agents; D011714:Pyrans; D014326:Tropanes
ZNS-Wirkstoffe: Synthese und Eigenschaften von 3-Anilino-8-oxatropanen.