In this work, different functionalized quinoline-2-one derivatives have been synthesized. The targeted compounds were designed to bear chloro, azido, fused tricycle, glycine, and sugar moieties. The synthesized derivatives have been screened for anticancer activity against HCT-116 cell line (human colon carcinoma) using MTT viability assay, for antioxidant activity using in vitro H2O2 scavenging activity method basing on iodometric titration with a modification and for antimicrobial activity against Gram-positive bacteria Staphylococcus aureus and Gram-negative bacteria Escherichia coli and against fungus strain of Candida albicans. Quinolone acylated arabinose hydrazone derivative 8 have the privilege amongst all the synthesized derivatives as it showed the best activity as an anticancer with IC50 23.5 μg/mL and it was the sole derivative that exhibited good antibacterial activity against the two strains of the tested bacteria. Results of antioxidant test revealed that quinolinonyl-glycine derivative 10 exhibited excellent H2O2 scavenging activity with IC50 20.92 μg/mL that surpassed the activity of ascorbic acid which is used as a reference. All the derivatives exhibited no antifungal activity against Candida albicans