Background: An upsurge in the number of antibiotic resistant microbial infections has warranted the discovery and developments of new antibiotics. This is a matter of grave concern for the effective therapy for search of novel antimicrobial agents. Literature is replete with the reports of involvement of oxidative stress due to imbalance between generation and neutralization of free radicals in many diseases. Heterocyclic compounds have been involved in the treatment of various disorders. Benzothiazole is one of such heterocyclic nucleus having benzene ring merged with thiazole ring. Among the various substitutions possible in this nucleus, substitutions at position-2 have already been reported with potential bioactivities. Thus different substituted compound have been synthesized which could serve as antimicrobials and antioxidant. Methods: Benzothiazole derivatives (B1-B7) were synthesized by two step reactions and the structures were confirmed through infrared, mass and NMR spectroscopy. The compounds were evaluated for in vitro antioxidant and antimicrobial activities using standard methods. Results: From the results of antibacterial and antifungal activity compound B4 was exhibited maximum activity against all the tested strains of microorganisms with the zone of inhibition 17.1-18.5 mm and MIC value 1.1-1.5 µg/mL. Compound B5 exhibited potent antioxidant activity. Conclusion: The compounds substituted with halogen on the aryl ring increased the antimicrobial activity as seen in the case of compound B4 (6-fluoro). The compounds substituted with hydroxyl group (B5) exhibited good antioxidant activity.