The ligand, (E)-4-((2-methoxyphenyl)amino)-4-oxobut-2-enoic acid, and its tri-butylstannyl (E)-4-((2-methoxyphenyl)amino)-4-oxobut-2-enoate, trimethylstannyl (E)-4-((2-methoxyphenyl)amino)-4-oxo but-2-enoate and triethylstannyl (E)-4-((2-methoxyphenyl)amino)-4-oxobut-2-enoate complexes wereobtained and characterized by different techniques. The spectroscopic data revealed the presence of the OH inthe FTIR and NMR spectra of the (E)-4-((2-methoxyphenyl)amino)-4-oxobut-2-enoic acid and the absence ofthis peak in the spectra of the complexes confirm their successful formation. The geometry confirmation wasdone using single-crystal X-ray diffraction and found a 5-coordinated distorted trigonal bipyramidal comprising of the O1 of the carboxylate moiety, O3 of the amide moiety occupying the axial position while thethree equatorial positions were occupied by the carbon atoms of the three butyl groups. The result of the DNAinteraction of the representative compounds explored an intercalative binding mode as confirmed by UV-Visible spectroscopy and viscometry. The in silico study performed by SwissADME webserver suggested thatreported compounds obey the rules of drug-likeness.