In the present study, a series of new indole-hydrazone derivatives were synthesized. The structures of the synthesized compounds were established on the basis of elemental and spectral (IR and 1 H-NMR) studies. All synthesized compounds were screened for their anti-inflammatory against carrageenan induced oedema in albino rats at a dose of 0.2 mmol/kg using indomethacin as a standard drug. The reduction in oedema formation was ranged between 72.3 -89.3 % for all the synthesized compounds compared to indomethacin (46 % inhibition). Moreover, their anticancer activity against breast cancer cell line (MCF-7) at a dose of 100µg/ml was evaluated. The compounds 2f and 2j showed mild anticancer activity (61% and 68% inhibition, respectively) compared to doxorubicin. Furthermore, all molecules were docked to the active site of both cox-1 and cox-2 using the docking program Molego virtual docker. All prepared compounds showed high docking score against both cox-1 and cox-2. The dock scores and binding energy were found to be in good agreement with the pharmacological results. Finally, the drug likeness and bioactivity were predicted using Molinspiration software. The results revealed that all new compounds show good drug likeness score and bioactivity score.