Galectin-3 is a unique member of a family of fifteen different galectins that are widely expressed in cells and bind to β-D-galactosides in mammals. Galectin-3 is postulated to serve an important role in various diseases such as fibrosis, inflammation and cancer. Herein, we describe the synthesis of a series of galectin-3 inhibitors in which we ultilize a tetrahydropyran core as a sugar replacement in subsite D of the galectin-3 carbohydrate recognition domain. Optimization of the substituents on the tetrahydropyran core resulted in potent galectin-3 inhibitors. The synthesis, structure–activity relationships, and biological evaluation of these novel tetrahydropyran-based galectin-3 inhibitors is presented.

Novel tetrahydropyran-based thiodisaccharide mimics as galectin-3 inhibitors

ACS Fall 2021

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