ScholarWorks@경상국립대학교

초록

In this study, we report a streamlined one-pot synthesis of a new series of (E)-4-phenyl-2-(2-(pyren-1-ylmethylene)hydrazinyl)thiazole derivatives (4a-4o). The reaction involves the condensation of pyrene-1-carbaldehyde, thiosemicarbazide, and alpha-halo ketones in the presence of a catalytic amount of InCl3 as a Lewis acid catalyst, carried out under reflux in a (1 : 1, v/v) H2O/EtOH medium at 80 degrees C. This protocol provides several key advantages, including mild reaction conditions, short reaction times, excellent yields, broad functional group tolerance, and the added benefit of chromatography-free product isolation, thereby enhancing practicality and operational simplicity. All synthesized compounds were fully characterized using 1H NMR, 13C NMR, FT-IR spectroscopy, and LC-MS analysis. The anticancer potential of the synthesized derivatives was evaluated against the human breast cancer cell line (MCF-7) using an in vitro MTT assay. Compounds 4m and 4g exhibited the most promising cytotoxic effects, displaying IC50 values of 43.66 and 45.24 mu g mL-1, respectively. Furthermore, molecular docking studies were performed to elucidate structure-activity relationships, revealing a strong correlation between the predicted binding affinities and the experimental biological outcomes.

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