ArticleBMC chemistry2026
Synthesis and biological evaluation of novel β-keto ether-triazole hybrids as dual antimicrobial and anticancer agents.
Article in BMC chemistry, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
The growing need for multifunctional agents to overcome antibiotic resistance and infection-related complications in immunocompromised cancer patients necessitates the development of dual-action therapeutics. Herein, a series of β-keto ether-triazole hybrids incorporating a 5-methyl-1-(4-nitrophenyl)-1 H-1,2,3-triazole moiety were synthesized via a one-step protocol and characterized by IR, NMR, and single-crystal X-ray diffraction. Crystallographic and Hirshfeld surface analyses revealed well-defined geometries stabilized by C-H···O and O-H···O interactions. DFT calculations showed excellent agreement with experimental structures (RMSD < 0.04 Å) and HOMO-LUMO energy gaps of 3.04-3.50 eV. MEP analysis indicated localized electrophilic regions in compound 3 and greater charge delocalization in compound 9. Biologically, compound 3 displayed potent antibiofilm activity, achieving 97% inhibition of methicillin-resistant Staphylococcus aureus, while compound 9 showed moderate yet selective cytotoxicity toward hepatocellular carcinoma cells (HepG2) (IC₅₀ = 63.28 µg/mL) with low toxicity to normal Wi38 cells. ADME profiling correlated solubility with antimicrobial activity and lipophilicity with cytotoxic effects, revealing that the high solubility of compound 3 favours antibacterial activity, while the greater lipophilicity and metabolic stability of compound 9 support its anticancer profile. These findings highlight β-keto ether-triazole hybrids as promising scaffolds for dual antimicrobial and anticancer applications.
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