title: [Conformationally restricted pethidine analogs. 5. Synthesis and pharmacologic testing of cis-B-10b-acyl-1,2,3,4,4a,5,6,10b- octahydrobenzo(f)isoquinolines].
abstract: Cyanophenylcyclobuten (1a) gave the corresponding cis-B-configurated 10b-acyloctahydrobenzo[f] isoquinolines 3a-f by Grignard reaction. Cis-B-3b was demethylated to yield the secondary base 3g, which in turn was realkylated to the homologous allyl- and isopentenyl derivatives 3h and 3i. In the writing test the desoxyketobemidon analogon cis-B-3b exhibits a remarkable activity, whereas 3a, c-e are somewhat weaker and 3h and 3i are inactive.
authors.affiliation: Institut für Pharmazie und Lebensmittelchemie, Universität München.
authors.forename: E
authors.initials: E
authors.lastname: Reimann
authors.forename: H D
authors.initials: HD
authors.lastname: Benend
authors.forename: G
authors.initials: G
authors.lastname: Höfner
mesh_terms: D000700:Analgesics / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D008614:Meperidine / Q000031:analogs & derivatives* / Q000494:pharmacology*; D051379:Mice; D008968:Molecular Conformation; D009020:Morphine / Q000494:pharmacology; D009270:Naloxone / Q000494:pharmacology; D010147:Pain Measurement / Q000187:drug effects; D011804:Quinolines / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000700:Analgesics; D011804:Quinolines; D009270:Naloxone; D009020:Morphine; D008614:Meperidine
vernacular_title: Pethidin-Analoga mit eingeschränkter Konformationsbeweglichkeit. 5. Mitteilung: Synthese und pharmacokologische Prüfung von cis-B-10b-Acyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]ischinolinen.