Synthesis, spectroscopic characterization and pharmacological studies on novel sulfamethaxazole based azo dyes

Abstract

The present work describes the synthesis of novel heterocyclic azo dyes by general diazo-coupling reaction of sulfamethoxazole with the various coupling compounds 5-methyl-2-phenyl-2, 4-dihydro-3H-pyrazol-3-one, 6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile and 1-ethyl-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile with good yield. The molecular structures of the newly synthesized compounds were confirmed by different spectroscopic techniques such as UV–Visible, FTIR, 1H NMR, Mass and elemental analysis. The in vitro biological screening of the synthesized compounds were tested against various microbial strains and results showed good activity compared with the standard drug. All the compounds exhibited promising anti-tubercular activity against Mycobacterium tuberculosis. The anticancer activity of the target compounds were screened against MCF-7, and compound A1 was found to be a potential anticancer agent with IC50 of 11.07 µg/mL. Also, the synthesized compounds studied for cleavage studies against CT-DNA by gel electrophoresis technique and all the compounds exhibited complete cleavage activity against CT-DNA. Keywords: Sulfamethaxazole, Azo dyes, Diazotization and anticancer activity