A series of divalent and one trivalent metal chelates of the azo ligand resulting from coupling of sulfafurazole diazonium chloride with resorcinol have been designed and synthesized. Structure investigation of the isolated chelates have been achieved by applying spectroscopic and analytical tools which collaborated to assure the formation of the metal chelates in the molar ratios of 1L: 1M for Ni(II), Co(II), and Fe(III) chelates, where Cu(II) and Zn(II) complexes formed in the ratio 2L : 1M. The geometrical arrangement around the metal canters was concluded from UV-Vis spectra to be octahedral for all metal chelates. The attachment of the ligand to the metal ions took place through the azo group nitrogen and o-hydroxyl oxygen through proton displacement leading to the ligand being in monobasic bidentate binding mode. Antimicrobial and antitumor activities of the interested compounds have been evaluated against alternative microorganisms and cancer cells, respectively, in a trial to investigate their extent of activity in addition to docking studies. The mode of interaction of the compounds with SS-DNA has been examined by UV-Vis spectra and viscosity studies.