Synthesis and the antimicrobial activity of 3-(2-methyl-4-oxo-1,4-dihydroquinoline-3-yl)propanoic acids

Abstract

In order to reveal the possible regularities of the structure–activity relationship the derivatives of 3-(2-methyl-4- oxo-1,4-dihydroquinoline-3-yl)propanoic acid having various substituents in α-position of the acidic moiety of propanoic acid such as alkyl, carboxyl, acyl and acetamide substituents have been synthesized. The synthesis of the target compounds has been carried out using 3-dimethylaminomethyl-2-methyl-1,4-dihydroquinoline-4-one as a versatile alkylating reagent. Its interaction with methylene active substances allowed to obtain monoalkyldicarbonyl compounds, which further hydrolysis gave the derivatives of 3-(2-methyl-4-oxo-1,4-dihydroquinoline-3yl)propanoic acid. The structures of the compounds obtained have been confirmed by the data of 1 H NMR and elemental analysis. The results of the screening performed by the agar diffusion method have shown different levels of the antimicrobial activity. For two compounds – 1,3-diethoxy-2-[(2-methyl-4-oxo-1,4-dihydroquinolin-3-yl)methyl]- 1,3-dioxopropan-2-yl-carbamic acid and 3-(2-methyl-4-oxo-1,4-dihydroquinolin-3-yl)propanoic acid a moderate broad-spectrum activity has been found in the screening method. The results of the research have shown the perspectiveness of further search for novel antibacterial agents based on 4-q