Background: The study aims to evaluate the potential of trifluoromethyl thioxanthene derivatives across various biological activities, including antioxidant properties, anti-amylase effects, pancreatic lipase inhibition, anticancer activity, and COX inhibition. This research offers insights into the therapeutic applications of these compounds for managing metabolic disorders and inflammation. Method: Tertiary alcohols were synthesized using Grignard reagents and subsequently combined with L-cysteine, with their structures confirmed via NMR and IR spectroscopy. Results: The results indicated compound 3 exhibited the highest antioxidant potential, with 46.6% at 80 μg/mL in the DPPH assay. Compound 4 showed moderate pancreatic lipase inhibition, exhibiting an IC50 range of 100.6 to 277 μM. Compound 1 revealed potent anticancer activity against HeLa cells, with an IC50 of 87.8 nM. Compound 2 showed a potent antioxidant and anti-amylase activity with IC50 of 1.67 ± 0.5 and 60.2 ± 0.8 μM, respectively. Furthermore, the synthesized compounds 1, 3, and 4 displayed promising COX-2 inhibition with IC50 values ranging from 6.5 to 27.4 nM, suggesting potential anti-inflammatory benefits. Conclusions: This study highlights the significant biological activities of trifluoromethyl thioxanthene derivatives, positioning them as promising candidates for the treatment of cancer, metabolic disorders, and inflammation. These compounds demonstrated noteworthy antioxidant and enzyme inhibition properties, warranting further in vivo studies to confirm their therapeutic efficacy.
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