Synthesis and pharmacological activity of 6-aryl-2-azabicyclo[4.2.1]nonanes.
A series of 6-phenyl-, 6-(m-methoxyphenyl)-, and 6-(m-hydroxyphenyl)-2-azabicyclo[4.2.1]nonanes was synthesized by a sequence involving alkylation of an appropriate 2-arylcyclopentanone with an aminoalkyl substituent. Subsequent ring closure at the other alpha position on the cyclopentanone ring and Wolff-Kishner reduction afforded the title compound. Several derivatives of these materials showed activity in an antinociceptive assay comparable to codeine. Most analogues were either inactive or toxic.
D000700:Analgesics / Q000138:chemical synthesis*; D000818:Animals; D001372:Aza Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D051379:Mice; D009043:Motor Activity / Q000187:drug effects; D011930:Reaction Time / Q000187:drug effects
D000700:Analgesics; D001372:Aza Compounds; D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds