Synthesis and Transformation of (-)-Isopulegol-Based Chiral β-Aminolactones and β-Aminoamides
AbstractA 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). View Full-Text
- Supplementary File 1:
PDF-Document (PDF, 2628 KB)
Share & Cite This Article
Le, T.M.; Bérdi, P.; Zupkó, I.; Fülöp, F.; Szakonyi, Z. Synthesis and Transformation of (-)-Isopulegol-Based Chiral β-Aminolactones and β-Aminoamides. Int. J. Mol. Sci. 2018, 19, 3522.
Le TM, Bérdi P, Zupkó I, Fülöp F, Szakonyi Z. Synthesis and Transformation of (-)-Isopulegol-Based Chiral β-Aminolactones and β-Aminoamides. International Journal of Molecular Sciences. 2018; 19(11):3522.Chicago/Turabian Style
Le, Tam M.; Bérdi, Péter; Zupkó, István; Fülöp, Ferenc; Szakonyi, Zsolt. 2018. "Synthesis and Transformation of (-)-Isopulegol-Based Chiral β-Aminolactones and β-Aminoamides." Int. J. Mol. Sci. 19, no. 11: 3522.
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.