7-Aza analogs of the analgetic agent azabicyclane. Synthesis and pharmacologic analysis.
Three 3,7-diazabicyclo[3.3.1]nonane derivatives (4) with a structural similarity to the analgetic agent azabicyclane (1) were prepared. The amino alcohol 4a was found to prefer a conformation wherein the six-membered ring to which the hydroxyl group is syn is in the boat form. These three compounds had increased basicity in comparison with 1 due to various forces stabilizing their monocationic states. Compounds 4a-c did not show analgetic activity at the dose levels tested.
D000700:Analgesics / Q000138:chemical synthesis*; D000818:Animals; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D019086:Bridged Bicyclo Compounds, Heterocyclic; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D005769:Gastrointestinal Motility / Q000187:drug effects; D051379:Mice; D008968:Molecular Conformation; D011809:Quinones / Q000037:antagonists & inhibitors; D011930:Reaction Time / Q000187:drug effects; D013035:Spasm / Q000517:prevention & control
D000700:Analgesics; D001372:Aza Compounds; D001643:Bridged Bicyclo Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D001952:Bridged-Ring Compounds; D011809:Quinones; C000109:azabicyclane