Synthesis of 4-methoxyphenoxyacetic and 3,4,5-trimethoxyphenoxyacetic acid amides and hydrazides as potential neurotropic and cardiovascular agents

Abstract

4-Methoxyphenoxyacetyl chloride, 3,4,5-trimethoxyphenoxyacetic acid and its methyl ester were reacted with 2-phenylethylamine, 1-benzylpiperazine, 1-(2-phenylethyl)piperazine, 1-(1-phenyl-2-propyl)piperazine, isopropylhydrazine, 1-aminopiperidine, and 4-aminomorpholine and afforded the amides and hydrazides Iab-IVab and Vb-VIIIb. 1-Amino-4-methylpiperazine and 1-amino-4-phenylpiperazine were transformed to the hydrazones XV and XVI, and to the quaternary salts XVII and XVIII. Pharmacological screening showed indications of thymoleptic activity with compounds Ia-IIIa, anorectic effect with IIa and IIIb, antiarrhythmic activity with IIIa, XVII, and XVIII, and myorelaxant effect with XVII and XVIII. Antimicrobial and anthelmintic effects were also noted.