Synthesis and Biological Studies of O3-Aryl Galactosides as Galectin Inhibitors

Research output: Contribution to journalArticle

Abstract

β-Galactose derivatives have recently been reported to selectively inhibit galectin-3, and a library of O3-arylated galactosides with varying substitution patterns was designed to study such inhibitions further. The O3-arylated galactosides were synthesized using diaryliodonium salts under mild and transition metal free conditions, providing the target products in moderate to good yields. An O3-trifluoroethylated galactoside was also synthesized using iodonium salt chemistry. Azido-substituted products were subsequently transformed into the corresponding triazoles. After deprotection, a selection of galactoside derivatives were evaluated for inhibitory potencies against galectins-1, 3, 4 N (N-terminal domain), 4 C (C-terminal domain), 7, 8 N, 8 C, 9 N, and 9 C and one compound with promising affinity and selectivity for both the N- and C-terminal domain of galectin-9 was discovered.

Details

Authors
Organisations
External organisations
  • Stockholm University
  • Eötvös Loránd University
  • Lund University
Research areas and keywords

Subject classification (UKÄ) – MANDATORY

  • Organic Chemistry
  • Biochemistry and Molecular Biology

Keywords

  • arylation, carbohydrates, galactosides, galectin inhibitor, hypervalent compounds
Original languageEnglish
JournalHelvetica Chimica Acta
Volume104
Issue number2
Early online date2020 Dec 22
Publication statusPublished - 2021
Publication categoryResearch
Peer-reviewedYes