Preparation of 7-(1,3,4-oxadiazolyl)-6,14-endo-etheno-6,7,8, 14-tetrahydrothebaines and related compounds as potential analgesics.
General procedures for the preparation of 7 alpha-(2-substituted-1,3, 4-oxadiazol-5-yl)-6,14-endo-etheno-6,7,8,14-tetrahydrothebaines are described. Substituents include alkyl, aryl, amino, cycloamino, and alkylthio functions. Many of these and related compounds show analgesic activity intermediate between codeine and morphine in the Hendershot and Forsaith writhing test. An unsuccessful attempt was made to synthesize 7 beta-(1,3,4-oxadiazol-2-yl)-6,14-endo-etheno-6,7,8,14- tetrahydrothebaine.
D000698:Analgesia; D000700:Analgesics / Q000138:chemical synthesis*; D000818:Animals; D004353:Drug Evaluation, Preclinical / Q000379:methods; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010069:Oxadiazoles / Q000138:chemical synthesis*; D051381:Rats; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship; D013797:Thebaine / Q000138:chemical synthesis*
D000700:Analgesics; D007202:Indicators and Reagents; D010069:Oxadiazoles; D013797:Thebaine