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RSS FeedsIJMS, Vol. 19, Pages 3522: Synthesis and Transformation of (-)-Isopulegol-Based Chiral ?-Aminolactones and ?-Aminoamides (International Journal of Molecular Sciences)

 
 

10 november 2018 15:02:02

 
IJMS, Vol. 19, Pages 3522: Synthesis and Transformation of (-)-Isopulegol-Based Chiral ?-Aminolactones and ?-Aminoamides (International Journal of Molecular Sciences)
 




A library of isopulegol-based β-amino acid derivatives has been developed from commercially-available (-)-isopulegol. Michael addition of primary and secondary amines towards α,β-unsaturated γ-lactones was accomplished resulting in β-aminolactones in highly-stereoselective reactions. Ring-opening of β-aminolactones with different amines furnished excellent yields of β-aminoamides. Moreover, the applicability of aminolactones in peptide synthesis was examined by opening the lactone ring with α- and β-aminoesters, providing dipeptides as promising chiral substrates for the synthesis of foldamers. The antiproliferative activities of β-aminolactones and β-aminoamides were explored, and the structure-activity relationships were studied from the aspects of the stereochemistry of the monoterpene ring and the substituent effects on the β-aminoamide ring system. The N-unsubstituted (-)-isopulegol-based β-aminoamides exhibited considerable antiproliferative activity against a panel of human adherent cancer cell lines (HeLa, MCF7 and MDA-MB-231).


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46 viewsCategory: Biochemistry, Biophysics, Molecular Biology
 
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