Recent work aimed at evaluating the possibility of enhancing biological activities by synthetically modifying bifunctional aldehyde structures. In this article, two series of bifunctional aldehydes were synthesized, structurally characterized (M-1A, M-1C and M-2A) using single crystal X-ray diffraction analysis. Several pharmacological properties like cytotoxic, antifungal, antibacterial, antioxidant and antitumor activities were also evaluated. In addition, bifunctional aldehyde-DNA interaction assay was examined by UV-Vis spectroscopy which revealed the DNA damaging behaviour of these aldehydes. The results of UV-Vis spectroscopy were supported by DNA damaging assay. The overall results reveal that bifunctional aldehyde moiety could be used as potential drug candidates.