In the present work, we report the facile synthesis, characterization and anticancer, antioxidant study of new imidazoquinoline carrying biologically active chalcone (2a–d) and pyrazoline (3a–d, 4a–d) moieties. Pyrazoline derivatives (3a–d, 4a–d) have been synthesized from the intermediate chalcones (2a–d) by cyclizing with hydrazine hydrate and phenyl hydrazine. The structures of these compounds were confirmed by IR, 1H NMR, 13C NMR and LC–MS. Biological studies of the synthesized compounds showed promising anticancer and antioxidant activities. The compounds were tested for their in vitro anticancer activity against human cell culture HeLa (cervical cancer) cell line. Compounds 2d and 3d showed the highest cytotoxicity. Compounds 2a, 2d and 3d are found to be the most effective antioxidant agents. Thus, the results show that synthesized compounds possess anticancer and antioxidant activity.