Synthesis and transformation of (-)-isopulegol-based chiral β-Aminolactones and β-Aminoamides

Tam Minh Le, Péter Bérdi, István Zupkó, Ferenc Fülöp, Zsolt Szakonyi

Research output: Contribution to journalArticle

2 Citations (Scopus)

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).

Original languageEnglish
Article number3522
JournalInternational journal of molecular sciences
Volume19
Issue number11
DOIs
Publication statusPublished - Nov 8 2018

Keywords

  • Antiproliferative activity
  • Dipeptide
  • Terpenoid
  • β-aminoamides
  • β-aminolactones

ASJC Scopus subject areas

  • Catalysis
  • Molecular Biology
  • Spectroscopy
  • Computer Science Applications
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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