Miniscule modification of Coumarin based dyes 4BMC and 4BBMC was molecularly designed and synthesized by a single-step method. The synthesized molecules such as 4BMC and 4BBMC were completely characterized by vital spectroscopic systems. The optimized molecular geometry and reactive parameters were resolved through the theoretical study to understand the molecular properties. The binding interaction of BSA and dyes were evaluated with the help of fluorescence quenching method, results exhibited a static type of BSA quenching. The mode of binding and binding constant was computed. The obtained results were further confirmed by using molecular docking analysis. Moreover, the antibacterial property of coumarin dyes were evaluated against one of the ESKAPE pathogen Pseudomonas aeruginosa. Two different strains of P.aeruginosa namely ATCC #9027 and ATCC#27853 which were reported to be multidrug resistant was used. Both the synthesized dyes were found to be effective in exhibiting their antibacterial action against the pathogen. Alongside the antibacterial activity, the antioxidant activity of two synthesized coumarin dyes were examined by employing DPPH, finally, the attained findings were evaluated with standard antioxidant ascorbic acid.