A series of chalcone derivatives 1a-c was synthesized according to green chemistry methodology using deep eutectic solvents as greener solvents. Chalcone 1a was used as a versatile starting material for the synthesis of variety of heterocyclic systems including isoxazoline, pyrazoline, pyrimidine and pyridine moieties. Elemental analyses and spectral data (IR, MS, 1H NMR, 13C NMR) were used to elucidate the structural formula of the products. The cytotoxicity of the prepared derivatives was screened using 3-[4,5-dimethylthiazole-2-yl]-2,5-diphenyltetrazoliumbromide (MTT) assay against three tumour cell lines. Additionally, antioxidant activity of the products was evaluated using 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging method. The results exhibited that a series of heterocyclic molecules including isoxazoline, pyrazoline, pyrimidine, pyridine, quinoline, and pyran derivatives was synthesized on the basis of green chemistry methodology using deep eutectic solvents as greener solvents. The cytotoxicity of the prepared derivatives was screened and pyrazoline 4 induced a significant growth inhibition towards tested cell lines while pyridone 7 showed the lowest activity. In addition, the antioxidant activity of the products was evaluated, where pyrazolines 2b and 3 demonstrated potent activity in comparison with ascorbic acid.