Structure—Activity Relationship of Local Anesthetics Based on Alkynylpiperidine Derivatives

Abstract

The influence of the nature of the acyl (propionyl and benzoyl) moiety and the piperidine ring C4 substituent on the activity of several alkynylpiperidine derivatives was studied. The presence of an alkyl (hexyl) radical on the triple bond of the piperidine ring C4 substituent in the infiltration anesthesia model had a positive effect on the anesthesia index and the duration of both total and general anesthesia as compared to lidocaine, novocaine, and trimecaine taken as reference drugs. The ester of 4-(octyn-1-yl)piperidol-1-propionic acid was the most active anesthetic among the studied compounds. Modification of the triple bond (exhaustive hydrogenation and hydration) led to a decrease in the duration of anesthesia. The activity of the benzoate was greater than that of the propionate in the propionate-benzoate pair.