Conformationally restrained fentanyl analogs. 2. Synthesis and analgetic evaluation of perhydro-1,6-naphthyridin-2-ones
- 1 October 1984
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 27 (10) , 1271-1275
- https://doi.org/10.1021/jm00376a007
Abstract
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, the trans-fused derivative nor the enamide possessed analgetic activity in the mouse tail-flick assay, reaffirming the sensitivity of this portion of 4-anilidopiperidine analgetics to conformational restraint.This publication has 11 references indexed in Scilit:
- Opiate receptor interaction of compounds derived from or structurally related to fentanylJournal of Medicinal Chemistry, 1981
- Synthesis and stereochemistry of 7-phenyl-2-propionanilidobenzo[a]quinolizidine derivatives. Structural probes of fentanyl analgesicsJournal of Medicinal Chemistry, 1981
- Evaluation of 2-Azabicyclo[2.2.2]loctane Analogs of 4-Anilidopiperidine AnalgesicsJournal of Pharmaceutical Sciences, 1980
- 4-Anilidopiperidine analgesics. 3. 1-Substituted 4-(propananilido)perhydroazepines as ring-expanded analogsJournal of Medicinal Chemistry, 1980
- 4-Anilidopiperidine analgesics. 2. A study of the conformational aspects of the analgesic activity of the 4-anilidopiperidines utilizing isomeric N-substituted 3-(propananilido)nortropane analogsJournal of Medicinal Chemistry, 1979
- Synthese und pharmakologische Prüfung von Pyridin‐Analoga des FentanylsArchiv der Pharmazie, 1978
- Synthesis of some conformationally restricted analogs of fentanylJournal of Medicinal Chemistry, 1977
- N-[4-(Methoxymethyl)-1-(2-phenylethyl)-4-piperidinyl]-N-phenylpropanamideActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1976
- Potentielle Analgetika, 5. Mitt.: Über die Synthese und pharmakologische Wirkung cyclischer Analoga des FentanylsArchiv der Pharmazie, 1975
- A SIMPLIFIED METHOD OF EVALUATING DOSE-EFFECT EXPERIMENTS1949