Resorcinarene-based macrocycles have garnered significant attention in drug delivery due to their selfassembly properties and unique topology. This study focuses on synthesizing a new resorcinarenebased macrocycle, incorporating a nitrobenzene molecule and amine derivative, to enhance therapeutic efficacy and enable conjugation with APIs for improved effectivity. The synthesized molecules were characterized using mass spectrometry and FT-IR spectroscopy, and their in vitro anticancer activity was evaluated through an MTT assay. At a concentration of 50 μg mL-1, the derivatives exhibited significant cytotoxicity against the A-549 (lung adenocarcinoma) cell line, achieving approximately 80 % cell death, compared to 97 % death caused by cisplatin. In vitro antimicrobial activity of the compounds was also tested against Micrococcus luteus, a gram-positive bacterium, with amikacin as the standard, at a concentration of 1 mg mL-1 through disc diffusion methods. Among the synthesized derivatives, compound-I showed antibacterial activity, producing a zone of inhibition of 18 mm, compared to the 27 mm zone of inhibition observed with amikacin. These promising results suggest that synthetically tuneable resorcinarene macrocycles and their analogues could emerge as potential lead compounds for anticancer and moderate antimicrobial therapies.