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Indole, a bicyclic heterocyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring, is a versatile structural motif in medicinal chemistry. Its unique structure allows it to interact with various biological targets, making it a valuable scaffold in drug design. Moreover, indole derivatives have been widely explored for their pharmacological activities, including antibacterial, antipsychotic, anticholinergic, anti-inflammatory, anticancer, antiviral, and antifungal properties.
A novel series of 3-(2-(1H-indol-2-yl)phenyl)-2-(substituted phenyl)-3,4-dihydroimidazo [4,5-b]indoles (4a–4j) was synthesized via condensation of 2-(o-aminophenyl)indole with aromatic aldehydes in ethanol. Structures were confirmed using FT-IR and 1H-NMR spectroscopy. The compounds were evaluated for antibacterial and antifungal activities, supported by molecular docking studies targeting Lanosterol 14-α demethylase and DNA Gyrase B.
Five compounds (4g, 4j, 4i, 4c, and 4b) showed significant antibacterial action against gram-positive B. subitilis and gram-negative E. coli and antifungal activity against C. albicans and A. niger. Molecular docking studies, performed in comparison with the standard drugs chloramphenicol and ketoconazole, revealed how the synthesized ligands bind within the active pockets. The results showed that compound 4b exhibits significant antibacterial activity, while compound 4c demonstrates good antifungal activity.
This study successfully synthesized a novel series of indole-based dihydroimidazo[4,5-b]indoles (4a–4j) with confirmed structures via FT-IR and 1H-NMR. Compounds 4b and 4c exhibited significant antibacterial and antifungal activities, respectively. Molecular docking revealed strong binding affinities with DNA Gyrase B and Lanosterol 14-α demethylase, supporting the observed bioactivity. These findings suggest promising potential for further antimicrobial drug development.
This study highlights the unique structures and potent antimicrobial activities of the synthesized compounds, showing their strong potential as novel antibacterial and antifungal agents with valuable therapeutic applications.