Conformationally restrained fentanyl analogues. 2. Synthesis and analgetic evaluation of perhydro-1,6-naphthyridin-2-ones.
Conformational flexibility of the N-acyl portion of fentanyl-type analgetics was restricted through the synthesis of novel perhydro-1,6-naphthyridin-2-one derivatives. Neither the cis-fused derivative (5a), the trans-fused derivative(5b), nor the enamide 8a possessed analgetic activity in the mouse tail-flick assay, reaffirming the sensitivity of this portion of 4-anilidopiperidine analgetics to conformational restraint.
D000698:Analgesia; D000700:Analgesics / Q000138:chemical synthesis*; D000818:Animals; D004353:Drug Evaluation, Preclinical; D005283:Fentanyl / Q000494:pharmacology; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D051379:Mice; D008968:Molecular Conformation; D009287:Naphthyridines / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
D000700:Analgesics; D007202:Indicators and Reagents; D009287:Naphthyridines; D005283:Fentanyl