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Synthesis, characterization, and biomedical assessment of novel bisimidazole–coumarin conjugates

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In an attempt to find versatile and readily accessible coumarin scaffolds with a broad spectrum of biomedical properties, seven bisimidazole–coumarin conjugates were synthesized through several steps starting from metacetamol and malonic acid. Spectroscopical techniques including FTIR, 1H-NMR, and 13C-NMR were employed to confirm the chemical backbone of the synthesized conjugates. Their biomedical potentials to behave as anti-tumorous, anti-aerobic gram-negative bacterial, anti-anaerobic bacterial, antifungal, free-radical quencher, and anticoagulant agents were evaluated. The anti-tumorous potential was investigated via an MTT-based assay against eight neoplastic-cell lines, while the anti-aerobic gram-negative bacterial potential was inspected using a broth-dilution assay against six standard bacterial strains. The anti-anaerobic bacterial potential was detected utilizing a Brucella-agar dilution assay against four standard bacterial strains, whereas the antifungal potential was estimated via a Sabouraud-dextrose broth dilution method against two standard fungal strains. The antioxidant potential was determined by following the capacity of the conjugates to quench the hydroxyl and DPPH radical phenotypes. Finally, the anticoagulant potential was detected in vivo by monitoring prothrombin-time following oral administration in rabbits. From the gathered outcomes, the author reported three main results. The conjugates have promising and broad biomedical effects. Conjugate Y7 has a potent and broad-range antineoplastic effect with a high capacity to quench the damaging free radicals, while being free from anticoagulant activity. Conjugate Y1 exhibited a potent antimicrobial activity with a spectrum involving pathogenic aerobic and anaerobic bacteria, and fungi. It is concluded that conjugate Y7 may represent a potential applicant as an antineoplastic agent, while conjugate Y1 may afford an agent that is free from anticoagulant activity with high potency as a broad spectrum antimicrobial compound.

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The author is very grateful to Dr. Mahmood Khudhayer Oglah for supplying the utilized chemicals. Also, many thanks to Dr. Mahmood Hashim Jasim for reviewing the academic writing of this work.

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Correspondence to Yasser Fakri Mustafa.

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Mustafa, Y.F. Synthesis, characterization, and biomedical assessment of novel bisimidazole–coumarin conjugates. Appl Nanosci 13, 1907–1918 (2023).

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