@article{fc0c513d-9775-4ea0-9fb5-a6f94f62e3f1,
  abstract     = {{A set of nineteen C-galactopyranosyl ligands, which included constrained compounds based on a bicyclic <em>trans</em>-decalin type system. were synthesized via click chemistry from 2-(β-d-<em>C</em>-galactopyranosyl) ethylene azide intermediates. The compounds were evaluated for binding to various galectins and the most promising inhibitor from the series was a constrained 3-<em>O</em>-benzylated galactopyranose derivative, with a trifluorophenyltriazole appendage; the ligand showed a <em>K</em><sub>D</sub> = 180 μM for Gal-4N, which is ∼7-fold better than lactose and ∼2-fold improved compared to thiodigalactoside; the compound was ∼5-fold selective for Gal-4N compared to Gal-4C. Molecular modelling suggested that the triazole C–H has potential to be involved in a non-classical H-bond with Glu87 carboxylate of Gal-4N, supported by increased affinity observed for trifluorophenyl substituted triazole when compared to fluorophenyl/phenyl derivatives. The modelling indicates that the benzyl aromatic ring may have Pi-Pi interactions with Phe/Trp, accounting for its ability to improve affinity.}},
  author       = {{Dhara, Ashis and Hever, Eoin and Sjövall, Fredrik and Leffler, Hakon and O'Malley, Ciaran and Nilsson, Ulf J. and Murphy, Paul V.}},
  issn         = {{0223-5234}},
  language     = {{eng}},
  month        = {{01}},
  publisher    = {{Elsevier Masson SAS}},
  series       = {{European Journal of Medicinal Chemistry}},
  title        = {{Synthesis of β-d-C-galactopyranosyl compounds including constrained derivatives from clickable building blocks and evaluation as ligands for galectins}},
  url          = {{http://dx.doi.org/10.1016/j.ejmech.2026.118613}},
  doi          = {{10.1016/j.ejmech.2026.118613}},
  volume       = {{308}},
  year         = {{2026}},
}