Unravelling the potential of 2-(Bromo/polybromophenylamino) substituted-4-arylthiazoles: Synthesis, characterization, anticancer, antimicrobial, molecular docking, and ADMET studies
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Date
2026
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Abstract
A total of twenty-four 2-(bromo/dibromo/tribromophenylamino)-4-arylthiazole derivatives (3a-x) were pre
pared to explore their biological potential, particularly to evaluate the effect of bromine substituent(s) on the
phenylamino group attached at position-2 of the thiazole nucleus. The reaction of α-bromoacetophenones with
different N-bromoarylthioureas at room temperature in alcohol afforded the target products in good yields. Their
structures were established based on analysis of spectroscopic data and results of single-crystal X-ray diffraction
technique. The anticancer evaluation revealed that compound 3p exhibited excellent selectivity (SI =8.86) with
an IC50 value of 129.37 ±8.0 μM toward lung cancer cells (A549), surpassing the standard drug, Carboplatin
(IC50 =128.83 ±2.0 μM, SI =1.21). It was observed that compounds possessing a 2,4-dibromophenylamino
moiety linked at position-2 of the thiazole ring demonstrated the highest selectivity for A549 cells and the
lowest cytotoxicity against Vero cells. Antimicrobial screening revealed that compounds 3g and 3h were highly
effective against the bacterial strain, Staphylococcus aureus, and the fungal strain Candida albicans, with MIC
values of 0.038 μg/mL (Ampicillin =1 μg/ml) and 0.021 μg/ml (Fluconazole =0.31 μg/ml), respectively.
Furthermore, molecular docking studies were conducted on the newly synthesized candidates, which support
their potential as effective biological agents. ADMET analysis for key pharmacokinetic and toxicological prop
erties of these compounds was also conducted to assess their drug-likeness nature.