| Abstract: | The simplified sialyl Lewisx mimic 5 containing a D ‐arabinose, a 3‐cyclohexyl‐2‐hydroxypropanoate, and a tetrahydropyran building block instead of L ‐fucose, sialic acid, and N‐acetylglucosamine, respectively was synthesized. Compound 5 was 10‐fold more potent than sLex in a static E‐selectin binding assay and showed at 50 μM 75% inhibition in a dynamic‐flow assay in which sLex did not inhibit neutrophil rolling at up to 1000 μM . Compound 7 with a lactic acid instead of sialic acid building block showed threefold improved potency compared to sLex. |
