Imines and lactones derived from friedelanes and their cytotoxic activity.

Nat Prod Res

Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte-MG, Brazil.

Published: March 2020

Friedelan-3-one () and friedelane-3,16-dione () isolated from leaves and branches of Reissek were subjected to structural modifications via nucleophilic addition to the carbonyl group and Baeyer-Villiger oxidation in order to synthesize potential cytotoxic compounds. The oximes friedelane-3-hydroxyimino () and 3-hydroxyiminofriedelan-16-one () together with the lactones friedelane-3,4-lactone () and 3,4-lactonefriedelan-16-one () were characterized by IR and NMR spectroscopic analyses. Compounds and are reported for the first time. Cytotoxic screening via MTT assay in human leukemia cell lines (THP-1 and K562) demonstrated no significant improvement of compounds when compared to the starting materials. Only compounds and demonstrated an improvement against K562 cells. However, the same assay on ovarian and breast cancer cell lines (TOV-21G and MDA-MB-231) showed a reduction in the IC for compounds , indicating that ring A modifications may enhance the biological potential.

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Source
http://dx.doi.org/10.1080/14786419.2018.1508137DOI Listing

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