Dihydropyrimidinone (DHPM) can be synthesized through a simple one-pot Biginelli reaction. Off-late medicinal properties of DHPM have been discovered. In our recent work, we have shown that the florescent property can be appended to this molecule while retaining its therapeutic attributes. DHPM derivatives have been substituted with different alkylating groups like ethyl-, mono-, di-, and tri- ethanol amines. This current paper discusses the multifunctionality of DHPM derivatives in form of anticancer and antimicrobial agent. DHPM derivatives exhibit improved inhibitory effects in in vitro anticancer assay. The synthesized DHPM derivatives are tested for their anti-cancer effects on A549 cell lines, as well as their anti-bacterial and anti-fungal effects on clinically significant pathogens like Staphylococcus aureus, Methicillin Resistant Staphylococcus aureus (MRSA), Escherichia coli, Colistin Resistant Escherichia coli, Pseudomonas aeruginosa, Candida albicans. These discoveries reveal good opportunity to develop multifunctional anticancer medicine based on DHPM. The synthesis and the presence of radical moieties in the DHPM derivatives have been supported by chemical studies.