Structure-Activity Relationship of 3- and 4-Acyloxy-1-(1, 3-dioxolan-4-ylmethyl) piperidine Derivatives

Abstract

Derivatives of 3- and 4-acyloxy-1-(1, 3-dioxolan-4-ylmethyl) piperidine were synthesized and tested for atropine-like activities on the ileum from guinea pigs. The structure-activity relationship was assessed. Features favoring potent atropine-like action were considered to be as follows : (1) both the acyloxy group and the dioxolane ring should be diequatorial on the piperidine ring, (2) the acyloxy group should be moderately bulky, and (3) a substituent on the dioxolane ring is unnecessary. The highest activity (pA₂) determined was 8.64 which is about 50 times that of scopolamine N-butyl bromide.