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Synthesis of symmetrical bis(indolyl)methanes via Sc(OTf)3 catalyzed tandem C–O and C–C bond breaking reaction and their anti-bacterial studies

Published in: Bioorganic & Medicinal Chemistry Letters, Volume 137, August 2026, 130623

DOI: 10.1016/j.bmcl.2026.130623

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Bis(indolyl)methanes (BIMs) are significant molecular scaffolds comprising nitrogen heterocycles that exhibit notable biological and pharmacological properties. This work represents an alternative and novel method for the synthesis of BIMs via a Sc(OTf)3-catalyzed tandem C–O and C–C bond-breaking reactions in β-hydroxyketone substrates. Our developed method involves the release of a unique yet unusual ketone leaving group. Anti-bacterial activity of some of the representative BIMs was evaluated against the bacterial strain Escherichia coli (E. Coli), and the results were compared with those of the standard, the broad-spectrum antibiotics ciprofloxacin and tetracycline. Most of the tested BIMs exhibited anti-bacterial activity with quantitative values. Notably, BIM 3l showed the highest anti-bacterial activity among all tested BIMs, with a zone of inhibition (ZI) value of 18.33 ± 1.52 mm, as compared to the standard antibiotics ciprofloxacin (25 ± 0.57) and tetracycline (28 ± 0.57).

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