A new series of 2-(3-Arylureido)benzoxazole (5a-j) derivatives were synthesized via sequential oxidative cyclisation, reduction followed by the reaction of resulting amine with different arylisocynates. All the synthesized compounds were screened for their in-vitro pro-inflammatory cytokines TNF-α and IL-6 inhibition and antimicrobial activity (antibacterial and antifungal). Among all the compounds screened, the compounds 5e found to be potent TNF-α and IL-6 inhibitor as compared to the standard dexamethasone but at the MIC of 10 μM, while the compounds 5f found to be moderately active as compared to standard dexamethasone. The remaining compounds were found to have low, very low or no activity at the MIC of 10 μM. The antimicrobial data revealed that compounds 5b, 5f, 5h and 5i found to be potent antibacterial and antifungal agents. Notably, the compounds 5b, 5h and 5i exhibited 1.5-2.5 fold antibacterial and antifungal activity to that of control drugs Micanazole and flucanazole almost against all the gram positive and gram negative bacteria and fungi and thus found to be more potent that the standard control drug.