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A series of ( Z )-2-benzylidenebenzofuran-3-(2H)-ones (aurones) bearing a variety of substituents on rings A and B were synthesized and evaluated for their antiparasitic activity against the intracellular amastigote form of  Leishmania infantum  and their cytotoxicity against human THP1-differentiated macrophages. In general, aurones bearing no substituents on ring A (compounds  4a–4f ) exhibit higher toxicity than aurones with 4,6-dimethoxy substitution (compounds  4g–4l ). Among the latter, two aurones possessing a 2′-methoxy or a 2′-methyl group (compounds  4i  and  4j ) exhibit potent antileishmanial activity (IC 50  = 1.3 ± 0.1  μ M and IC 50  = 1.6 ± 0.2  μ M, resp.), comparable to the activity of the reference drug Amphotericin B, whereas they present significantly lower cytotoxicity than Amphotericin B as deduced by the higher selectivity index.

Aurones: A Promising Heterocyclic Scaffold for the Development of Potent Antileishmanial Agents