A series of novel bioactive chemical compounds were synthesised to combat drug resistance in both microorganisms and cancers. The compounds were synthesised in conventional laboratory settings, as well as with the use of microwave irradiation, to develop a more efficient synthesis methodology. In summary, a total of 20 compounds were synthesised and their antimicrobial and anticancer properties were evaluated. These compounds were found to be moderately active against the selected microorganism strains, while remarkably cytotoxic to the selected cancer cells. An improved methodology to synthesise the compounds using microwave irradiation was also established.