Synthesis of benzoxazole derivatives via Mannich reaction yielded 6-methyl-2-{[(substituted-phenyl)amino]methyl}[1,2,4]triazolo[3,4-b][1,3]benzoxazole-3(2H)-thiones 3(a–f) and 3-[2-(5-methyl-1,3-benzoxazol-2-yl)hydrazinylidene]-1-[(substituted-phenylamino)methyl]-1,3-dihydro-2H-indol-2-ones 5(a-f). The characterization of target moieties was defended by their spectral data analysis. The newly synthesized compounds were assessed by invitro cytotoxic activity by colorimetric MTT assay against MCF-7 human breast cancer cell line at varied concentrations. The results of MTT assay were shown as % cell viability and IC50(μM) values. The invitro antibacterial, antifungal evaluation with different bacterial and fungal strains exhibited significant MIC values attributed to gratifying antimicrobial potency of target molecules. Molecular docking simulation of the target molecules was carried on NQO 2 (PDB ID: 4ZVM) protein receptor to complement the invitro cytotoxicity. The ADMET properties description has promoted the drug like properties of the target molecules.