Antileishmanial activities of dihydrochalcones from piper elongatum and synthetic related compounds. Structural requirements for activity
- 1 September 2003
- journal article
- Published by Elsevier BV in Bioorganic & Medicinal Chemistry
- Vol. 11 (18), 3975-3980
- https://doi.org/10.1016/s0968-0896(03)00406-1
Abstract
Two dihydrochalcones (1 and 2) were isolated from Piper elongatum Vahl by activity-guided fractionation against extracellular promastigotes of Leishmania braziliensis in vitro. Their structures were elucidated by spectral analysis, including homonuclear and heteronuclear correlation NMR experiments. Derivatives 3–7 and 20 synthetic related compounds (8–27) were also assayed to establish the structural requirements for antileishmanial activity. Compounds 1–11 that proved to be more active that ketoconazol, used as positive control, were further assayed against promastigotes of Leishmania tropica and Leishmania infantum. Compounds 7 and 11, with a C6–C3–C6 system, proved to be the most promising compounds, with IC50 values of 2.98 and 3.65 μg/mL, respectively, and exhibited no toxic effect on macrophages (around 90% viability). Correlation between the molecular structures and antileishmanial activity is discussed in detail.Keywords
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