MyJournals Home  

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). Digg Facebook Google StumbleUpon Twitter
66 viewsCategory: Biochemistry, Biophysics, Molecular Biology
IJMS, Vol. 19, Pages 3523: Hypoxic Microenvironment and Metastatic Bone Disease (International Journal of Molecular Sciences)
IJMS, Vol. 19, Pages 3521: Ultrastructural and Molecular Analysis of Ribose-Induced Glycated Reconstructed Human Skin (International Journal of Molecular Sciences)
blog comments powered by Disqus
The latest issues of all your favorite science journals on one page


Register | Retrieve


Molecular Biology

Use these buttons to bookmark us: Digg Facebook Google StumbleUpon Twitter

Valid HTML 4.01 Transitional
Copyright © 2008 - 2019 Indigonet Services B.V.. Contact: Tim Hulsen. Read here our privacy notice.
Other websites of Indigonet Services B.V.: Nieuws Vacatures News Tweets Travel Photos Nachrichten Indigonet Finances Leer Mandarijn