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Int. J. Mol. Sci. 2018, 19(11), 3522; https://doi.org/10.3390/ijms19113522

Synthesis and Transformation of (-)-Isopulegol-Based Chiral β-Aminolactones and β-Aminoamides

1
Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös utca 6, Hungary
2
Stereochemistry Research Group of the Hungarian Academy of Sciences, H-6720 Szeged, Eötvös utca 6, Hungary
3
Department of Pharmacodynamics and Biopharmacy, University of Szeged, H-6720 Szeged, Eötvös utca 6, Hungary
4
Interdisciplinary Centre of Natural Products, University of Szeged, H-6720 Szeged, Eötvös utca 6, Hungary
*
Author to whom correspondence should be addressed.
Received: 28 September 2018 / Revised: 31 October 2018 / Accepted: 5 November 2018 / Published: 8 November 2018
(This article belongs to the Special Issue Natural and Semi-Synthetic Small Molecules in Drug Discovery)
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Abstract

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). View Full-Text
Keywords: terpenoid; β-aminolactones; β-aminoamides; dipeptide; antiproliferative activity terpenoid; β-aminolactones; β-aminoamides; dipeptide; antiproliferative activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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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.

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