Synthesis, characterization and pharmacological evaluation of 2-aminothiazole incorporated azo dyes

Abstract

Azo molecules (A1-A3) were prepared by reacting 2-aminothiazole with three different pyridone derivatives as coupling components, viz., 6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile, 6-hydroxy-1,4-dimethyl-2-oxo-1,2-dihydropyridine-3-nitrile and 1-ethyl-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile via diazo-coupling reactions, under appropriate experimental conditions. The structural characteristics of the synthesized compounds were checked by different spectral techniques. The newly synthesized molecules were tested for their biological activities and the results of biological activity studies of the compounds prepared exhibited potential antimicrobial activity against the respective microorganisms. The synthesized azo dyes also demonstrated promising antimycobacterial activity screened against M. tuberculosis. All the compounds showed considerable cleavage efficiency against supercoiled pBR322 DNA. Further, the in silico molecular docking study was performed against E. coli 24 kDa domain and Cyp51 (cytochrome P450 14α-sterol demethylase) as target receptors. The binding energy of each studied compound was evaluated, and the data revealed that the compound A1 displayed higher binding affinity value and forms hydrogen bonds with the active amino acids.