The 7-methoxy-2-(4-thiomethylphenyl)-1-benzofuran-5-carbaldehyde was synthesised by known literature method (Wittig reaction approach) from vanillin. To deduce the anticancer and antibacterial activity of the 7-methoxy-2-(4- thiomethylphenyl)-1-benzofuran-5-carbaldehyde, it is docked with different biomarkers of cancer cell and bacteria. Grid was generated for each oncoproteins by specifying the active site amino acids. The binding model of best scoring analogue with each protein was assessed from their G-scores and disclosed by docking analysis using the XP visualizer tool. An analysis of the receptor-ligand interaction studies revealed that 7-methoxy-2-(4- thiomethylphenyl)-1-benzofuran-5-carbaldehyde is most active against 1BAG and 4FNY biomarkers and have the features to prove themselves as anticancer drugs. It shows strong cytotoxicity against human cell line [lung (A-459) and breast (MCF-07)].