Substituted lactose derivatives as cell adhesion inhibitors

摘要

Compounds and methods of making them having formula (I) are described which bind to selectin receptors and thus modulate the course of inflammation, cancer and related diseases by modulating cell-cell adhesion events. In formula (I), R1 is independently H or lower alkyl(1-4C); R2 is H, OH or lower alkyl(1-4C), alkylaryl or one or more additional saccharide residues; R3 is a negatively charged moiety including SO4--, PO4--, or related group; Y is H or lower alkyl(1-4C); and X is -CHR4(CHOR1)2CHR5OR1 wherein R4 and R5 are each independently H, lower alkyl(1-4C), or taken together result in a five- or six-membered ring optionally containing a heteroatom selected from the group consisting of O, S, and NR1; said five- or six-membered ring optionally substituted with one substituent selected from the group consisting of R1, CH2OR1, OR1, OOCR1, NR12, NHCOR1, and SR1 with the proviso that if X represents a hexose substituent R3 and R4, taken together, cannot provide a hexose substituent.