The present work discusses the synthesis and structure elucidation of azo ligand named 3,4‐dimethylisoxazol‐5‐yl‐4‐((3‐formyl‐4‐hydroxyphenyl)diazenyl) benzenesulfonamide (abbreviated as MIBS). MIBS ligand has been employed for the synthesis of a series of transition metal chelates in which the transition metal incorporated are Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II) and Cd(II). The isolated metal chelates have been demonstrated to be formed in 1:1 (M:L) ratio for all complexes excluding the Cd(II) chelate which have 1:2 (M:L) composition. The mode of bonding of the ligand towards the metal centre has been concluded from inspection of the FTIR spectra of both ligand and complexes, providing that the ligand attached to the meal centres through the carbonyl and deprotonated hydroxyl oxygen atoms. The geometry of the formed complexes has been proved to be tetrahedral for Mn(II), Co(II), Zn(II) and Cd(II) compounds and octahedral for the remaining chelates. Bioassay investigation of the synthesized compounds against Gram‐negative and Gram‐negative bacteria and fungi has been performed in comparison with familiar standard drugs. Among the tested compounds, Cd(II) and Co(II) complexes showed the highest activity against the tested microorganisms, which is in good matching with docking studies. The interaction manner of the isolated compounds with SS‐DNA has been inspected by means of electronic absorption titration and viscosity studies.