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, 1 H NMR, 13 C 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]-2,5diphenyltetrazoliumbromide (MTT) assay against three tumour cell lines namely; hepatocellular carcinoma (HePG-2), mammary gland (MCF-7) and colorectala denocarcinoma (Caco-2) where the cytotoxic effects showed that pyrazoline derivatives(4 ) induced a significant growth inhibition towards tested cell lines while1,2-dihydropyridine-3-carbonitrile derivatives (7) showed the lowest activity. Additionally, antioxidant activity of the products was evaluated using 2, 2diphenyl-2-picrylhydrazyl (DPPH) radical scavenging method, the results exhibited that compounds 4,5-dihydro-1H-pyrazole-1-carbothioamide (2b) and 4,5-dihydro-1H-pyrazole (3) showed potent activity in comparison with ascorbic acid as standard.