Abdel' N. Synthesis, structure and antituberculosis activity of fluorosubstituted amides of 1-R-2-oxo-4-hydroxyquinoline-3-carboxylic acids

Alkylation reaction of 1H-2-oxo-3-carbethoxy-4-hydroxyquinoline with iodoethane in the presence of potassium carbonate has been studied. 4-Ethoxy derivative has been proved to be the main product of the reaction mentioned in spite of the solvent used. There has been an attempt to perform N-alkylation 1H-2-oxo-3-carbethoxy-4-hydroxyquinoline after blocking of 4-hydroxy group, and a low efficiency of 4-O-acetyl capping group has been shavn. At the same time alkylation of 1H-2-oxo-3-carbethoxy-4-chloroquinoline by the normal structure alkylhalogenides with the further transformation of 1-alkyl-4-chloroquinolines in 4-hydroxy derivatives can be recommended as a preparative method for obtaining esters of 1-alkyl-2-oxo-4-hydroxyquinolin-3-carboxylic acids. Several ways of their obtaining have been studied, and the synthesis of fluoro-substituted anilides and benzylamides of 1-R-2-oxo-4-hydroxyquinoline-3-carboxylic acids has been carried out. The structure of the compounds obtained has been confirmed by thedata of ultimate analysis and NMR spectra and in some cases by counter synthesis and X-ray diffraction analysis. The microbiological screening of the substances obtained has been performed. 3'-Fluoroanilide of 1-butyl-2-oxo-4-hydroxyquinoline-3-carboxylic acid has been recommended for profound pharmacological research as a potential drug for tuberculosis and non-tuberculosis micobacterioses.