Synthesis and biological activity of arylheteraaliphatic amino amides

Abstract

The synthesis of a series of N-substituted arylheteraaliphatic amino amides was carried out to determine their antiarrhythmic activity. Styrene oxide was the initial compound for the synthesis. Its oxirane ring was opened with N,N-dialkylaminoethanols in the presence of alcoholates. It was found that the opening of the oxirane ring was carried out mainly according to the Krasusky rule on the bond between the oxygen atom and the less substituted carbon atom. A mixture of two products with the predominance of the secondary amino alcohol was created. The main product was separated by multiple vacuum distillations. 2-[2-(Dialkylamino) ethoxy]-1-phenylethanols were obtained and used in the Ritter reaction for the alkylation of benzonitrile in the presence of sulfuric acid to give N-{2-[2-(dialkylamino)ethoxy]-1-phenylethyl} benzamides. Biological tests of the obtained compounds were carried on the aconitine arrhythmia model out in rats. Procainamide, Quinidine, Lidocaine and Ethacyzin were used as the drugs. The findings in this study indicate that most of the obtained compounds have a low toxicity and expressed antiarrhythmic activity.

Keywords

• 2-[2-(dialkylamino)ethoxy]-1-phenylethanols, n-{2-[2-(dialkylamino)ethoxy]-1- phenylethyl}benzamides, the krasusky rule, the ritter reaction, antiarrhythmic activity