Bio-Inhibitors like covalent organic framework of differently substituted alkyl phenylacetates (DSPA: 2.1-2.12) to control microbial toxicities and other budding threats were synthesized. The structures of the synthesized drug candidates were characterized through IR, 1H-NMR, 13C-NMR spectral data and the molecular weight determination with fragmental futures using Mass Spectrometry. After proper validation of the docking protocol, the in-silico analysis of different disease condition like anti-analgesic, anti-inflammatory and anti-cancer targets (PDB ID: 5du1, 5glw and 6fe2) against the synthesized drug candidates DSPA: 2.1-2.12 have been investigated by AutoDock 4.2 application. The studied docking data analysis revealed that the drug candidates 2-Butyl 4-methoxyphenylacetate (2.3) and Methyl 3,4-dimethoxyphenylacetate (2.5) are potentially inhibits anti-analgesic/anti-inflammatory proteins 5du1/5glw and anti-breast cancer protein 6fe2 respectively are useful compounds for the prevention of the diseases. The % of inhibitions at a concentration of 400 μg/ml are found to be 76.6565, 78.8991, 74.5158, 79.8165 and 82.2630 for 2.4a, 2.11a, 2.11, 2.12a and diclofenac sodium respectively, with a biological anti-inflammatory activity order of 2.11˂ 2.4a ˂ 2.11a ˂ 2.12a ˂ diclofenac sodium. The synthesized ligands have shown a very impressive anti-breast cancer activity, drug candidate 2.4 with para-methoxy group in its structure has displayed devastating anti-inflammatory effect when compared with the standard doxorubicin.