Synthesis and Pharmacological Action of 4-Dimethylaminoalkyl-4-(m-methoxyphenyl)cycloalkanol Derivatives (Organic)

Abstract

For the purpose of testing their biological activity, 4-dimethylaminoalkyl-4-(m-methoxyphenyl) cycloalkanol derivatives (VIII to XI) were synthesized from 1-(m-methoxyphenyl)-4-acetoxycyclohexane dimethylamide derivatives (XVIII to XX and XXIX), which were obtained from 1-(m-methoxyphenyl)-4-acetoxycyclohexanecarboxylic acid derivatives (XII to XIV) and 1-(m-methoxyphenyl)-4-hydroxycycloheptanecarboxylic acid (XXV), in tetrahydrofuran with lithium aluminium hydride. 1-Dimethylaminomethyl-1-(m-methoxyphenyl)-4-acetoxy- or benzoyloxy-cycloalkanes (XXIII, XXIV, and XXXII) were prepared by acetylation or benzoylation of VIII and XI. Some of the compounds were found to have a considerably lower anticholinesterase activity than galanthamine (I), as shown in Table I.