抄録
As part of study on the structure-activity relationships of phenylazabicycloalkane analgetics, the title compound (I) has been synthesized. Structure (I) could be regarded as a piperidine analog of 1-phenyl-6-azabicyclo [3. 2. 1] octane (II), a known partial agonist, and also as a conformationally constrained analog of the 3-phenyl-piperidine analygetics (XIX). From the keto ester (III), I was obtained by the sequence of reactions outlined in Chart 2. Neither by the AcOH writhing nor by the hot-plate method, I exhibited appreciable analgetic activity. In contrast, the N-methyl compounds (XIV and XV) showed narcotic antagonist activity, with the former being the more active. Replacement of the N-methyl group of XV by a propyl and an allyl group (XVIIIa, d) resulted in an increase in the antagonist activity. Their activity was about one-tenth that of nalorphine.
