Bioorganic and Medicinal Chemistry Letters
Bioorganic and Medicinal Chemistry Letters
5 years ago

Syntheses of cytotoxic novel arctigenin derivatives bearing halogen and alkyl groups on aromatic rings

Syntheses of cytotoxic novel arctigenin derivatives bearing halogen and alkyl groups on aromatic rings
The new lignano-9,9′-lactones (α,β-dibenzyl-γ-butyrolactone lignans), which showed the higher cytotoxicity than arctigenin, were synthesized. The well-known cytotoxic arctigenin showed activity against HL-60 cells (EC50 =12μM), however, it was inactive against HeLa cells (EC50 >100μM). The synthesized (3,4-dichloro, 2′-butoxy)-derivative 55 and (3,4-dichloro, 4′-butyl)-derivative 66 bearing the lignano-9,9′-lactone structures showed the EC50 values of 10μM and 9.4μM against HL-60 cells, respectively. Against HeLa cells, the EC50 value of the derivative 66 was 27μM. By comparing the activities with the corresponding 9,9′-epoxy structure (tetrahydrofuran compounds), the importance of the lactone structure of 55 and 66 for the higher activities was shown. The substituents on the aromatic ring of the lignano-9,9′-lactones affected the cytotoxicity level, observing more than 10-fold difference.

Publisher URL: www.sciencedirect.com/science

DOI: S0960894X17306832

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