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In search of a new class of biologically active agents, some novel oxazolidinone-thiazole hybrids 4a–m have been synthesized and characterized on the basis of a combined use of infrared, NMR (1H, 13C) spectroscopy, mass spectrometry and elemental analysis. All compounds were evaluated for their antimicrobial, antioxidant and ultraviolet mediated DNA damage protective activity. Among the series, compound 4i emerged as the most potent antimicrobial agent, particularly, against Bacillus subtilis, Candida albicans and Saccharomyces cerevisiae in comparison to the standard drugs, Ciprofloxacin (antibacterial) and Amphotericin-B (antifungal). Other promising antimicrobial agents including the compounds 4f–h. In addition, all compounds 4a–m were found to show very high DNA damage protecting ability under ultraviolet irradiation. The antioxidant study revealed that the compounds 4d and 4j were found as the most potent antioxidants as compared to ascorbic acid, a reference compound considered in the study.