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Background: Thymol, a natural monoterpenoid compound found in thyme species, acts as a promising molecule for drug development. Linking thymol with aryl amines via azo coupling markedly improves its therapeutic property, resulting in the creation of multipurpose agents that have strong antimicrobial, antioxidant, and anticancer activities. Objective: In this present study, a new series of thymol-based azo-derivatives was synthesized and assessed for in vitro antimicrobial, antioxidant, and anticancer activity. Methodology: In this study, a series of thymol-azo-aryl derivatives were synthesized, and various techniques, such as FTIR, NMR (1H and 13C), MS, and elemental analysis, were used to confirm their structure. After synthesizing the new compounds, they were tested for in vitro biological activities. This included testing their antimicrobial potential by using the tube dilution assay and measuring their antioxidant capacity by the DPPH method. Finally, we explored their therapeutic potential by assessing their inhibitory effects on A-549 cancer cell growth through MTT assays. Result: Among the tested compounds, H2 really stood out with its broad-spectrum antimicrobial punch, hitting MIC values as low as 0.04 μg/mL against E. faecalis, 0.06 μg/mL for S. aureus, 0.07 μg/mL versus P. aeruginosa, and 0.06 μg/mL against E. coli. Additionally, H2 also demonstrated the most potent antifungal activity, achieving MIC values of 0.04 μg/mL against C. albicans and 0.05 μg/mL against A. niger. In terms of antioxidant capacity, H14 was the most effective, yielding an IC50 = 9.70 μg/mL value, which actually surpasses the standard antioxidant, ascorbic acid. H21 exhibited significant anticancer efficacy (IC50 = 286.57 nM), surpassing doxorubicin. Discussion: This study demonstrated that the incorporation of the azo group into the thymol moiety substantially enhances its biological profile. Notably, derivatives H2, H14, and H21 exhibited significant antimicrobial, antioxidant, and anticancer effects, underscoring the therapeutic potential of these modifications for novel drug development. Conclusion: The newly synthesized thymol azo derivatives exhibited potent antimicrobial, antioxidant, and anticancer properties. Mainly, H2, H14, and H21 showed the best biological activity. These findings suggest that these compounds could serve as potential lead structures for future drug discovery and development efforts.