The properties of 1-alkoxymethyl-3-hydroxypyridinium and 1-alkoxymethyl-3-dimethylaminopyridinium chlorides

Abstract

Several 1-alkoxymethyl-3-substituted-pyridinium chlorides with alkoxy chains including from 3 to 18 carbon atoms were prepared by the reaction of 3-substituted-pyridine with chloromethyl alkyl ethers. The prepared chlorides were examined for their antielectrostatic effects and their antimicrobial activities. 1-Dodecyloxymethyl-3-dimethylaminopyridinium chloride (23) exhibited strong antimicrobial activity and a wide antimicrobial spectrum, similar to the activity of benzalkonium chloride. We synthesized 1-alkoxymethyl-3-hydroxypyridinium chlorides possessing antielectrostatic properties, but lacking antimicrobial activity. The antielectrostatic effect and antimicrobial activities are strongly dependent on the kind of substituent at the 3-position in the pyridine ring and are greatly affected by an alkoxy chain. It was shown that dimethylamino group in position three must be present for a high antielectrostatic and antimicrobial activity of the agent.