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

Gabriella Kervefors, Kumar Bhaskar Pal, Gergely L. Tolnai, Mukul Mahanti, Hakon Leffler, Ulf J. Nilsson, Berit Olofsson

Research output: Contribution to journalArticlepeer-review


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.

Original languageEnglish
JournalHelvetica Chimica Acta
Issue number2
Early online date2020 Dec 22
Publication statusPublished - 2021

Subject classification (UKÄ)

  • Organic Chemistry
  • Biochemistry and Molecular Biology

Free keywords

  • arylation
  • carbohydrates
  • galactosides
  • galectin inhibitor
  • hypervalent compounds


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