[Synthesis, stereochemistry and analgesic action of 3,7-diazabicyclo[3.3.1] nonan-9-ones and 1,3-diazaadamantan-6-ones].
The 1,3-diazaadamantan-6-ones 13-18 are synthesized from the 4-piperidones 1-3. Different conditions lead to stereoisomeric structures. The 3,7-diazabicyclo[3.3.1]nonan-9-ones 8 and 9 show similar geometrical isomerisms. The configuration is determined by means of 1H-NMR and 13C-NMR spectroscopic data. Whereas the diazabicyclo[3.3.1]nonanones 7 and 12 show opioid-like effects, the diazaadamantanone 13 is a peripheral analgesic.
Samhammer
A
A
Holzgrabe
U
U
Haller
R
R
D000218:Adamantane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000700:Analgesics / Q000138:chemical synthesis*; D000818:Animals; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D051379:Mice; D013237:Stereoisomerism
D000700:Analgesics; D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds; D000218:Adamantane
Synthese, Stereochemie und analgetische Wirkung von 3,7-Diazabicyclo[3.3.1]nonan-9-onen und 1,3-Diazaadamantan-6-onen.