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- W1751580212 abstract "Abstract The synthesis of novel aza-derivatives of THF lignan natural products has been achieved. This synthesis originates in the use of a highly selective acyl-Claisen reaction to provide a syn morpholine amide which ultimately determines a trans relationship at the 3- and 4-positions on the central ring. Initial attempts at the synthesis resulted in premature cyclisation, producing either dihydro-pyrrole or tetrahydrofuran structures. Later stage introduction of the amine functionality resulted in successful synthesis of aza-lignans. This synthesis allows for several variations in the aza-lignan structure, including the substitution on the aromatic ring and the amine that can be incorporated, resulting in the synthesis of a range of aza-analogues of fragransin A2 and galbelgin. Furthermore, these analogues have been tested for their anti-proliferative properties against various human cancer cell lines, along with their naturally occurring THF counterparts. Results show that for most cases, aza-derivatives are more active than the corresponding THF compound, with the most active compound, the aza-derivative of fragransin A2, IC50 5.1 μM against a human breast cancer cell line." @default.
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- W1751580212 date "2015-12-01" @default.
- W1751580212 modified "2023-09-25" @default.
- W1751580212 title "Synthesis of aza-derivatives of tetrahydrofuran lignan natural products" @default.
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- W1751580212 doi "https://doi.org/10.1016/j.tet.2015.10.050" @default.
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