Synthesis of novel Sialyl-Lewis(X) glycomimetics as selectin antagonists

Article abstract of DOI:10.1016/S0040-4020(98)00105-7

A series of low molecular weight sialyl-Lewis(X) analogs based on either rigid or flexible replacements for the carbohydrates were designed as orally available anti-inflammatory drugs, synthesized and tested in cell-based adhesion assays. The flexible glycomimetic 7a lacking any glycoside or peptide linkage was prepared in 4 steps and 41% overall yield from methyl 3,5-dihydroxybenzoate and the fucose derivative 18 and exhibited about equal binding affinity to E- and P-selectin compared to the parent tetrasaccharide.