Parshikov V. Synthesis, physical, chemical and biological properties of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acids derivatives

The research deals with the investigation of new biologically active substances possessing diuretic effect in the number of 1R-4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acids N-R-amides. The interactions of ethyl ethers 4-chloro-2-oxo-1,2-dihydroquinoline-3-carboxilic acids with methylene-active compounds (ethyl cyano-acetate or malononitrile) was studied and the simple method of substitute chlorine atom on methyl group is developed. The most optimum schemes of synthesis of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acids alkylamides, anilides and hetarylamides were found out and realized. To confirm the structure of synthesized substances elementary analysis, spectroscopy NMR (including COSY, HMQC, HMBC methods), mass-, chromatomass-spectrometry, thin-layer chromatography and X-ray structural analysis were applied. Diuretic activity of all synthesized 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acids N-R-amides was studied. Correlation between structure and diuretic action was revealed. As a result 4-methyl-2-oxo-1,2dihydroquinoline-3-carboxylic acid 4-methoxyanilide as perspective diuretic agent can be recommended.