Synthesis and antibacterial activity of N-carboxyethyl-N-(4-hydroxyphenyl)-2-aminothiazoles and dihydrothiazolones

Abstract

New 2-aminothiazole and 2-aminodihydrothiazole derivatives with carboxyethyl, aromatic, and heterocyclic moieties were synthesized from N-(4-hydroxyphenyl)-N-thiocarbamoyl-β-alanine as a starting material. This thioureido derivative was found to be a useful intermediate for the synthesis of various substituted thiazole derivatives. The structure of the new compounds was confirmed by chemical and spectroscopic methods. Antibacterial evaluation of synthesized compounds was explored against Rhizobium radiobacter. It was found that among all synthesized compounds, the highest antibacterial activity was exhibited by compound 3-[{5-[(2E)-3-(4-chlorophenyl)prop-2-enoyl]-4-methyl-1,3-thia­zol-2-yl}(4-hydroxyphenyl)amino]propanoic acid at 75–1 000 µg/ml concentrations.