Design and synthesis of sialyl Lewis x mimics as E-selectin inhibitors

• Published in: Bioorganic & medicinal chemistry letters Vol. 11; no. 2; pp. 151 - 155
• Main Authors: KAILA, Neelu, THOMAS, Bert E, THAKKER, Paresh, ALVAREZ, Juan C, CAMPHAUSEN, Raymond T, CROMMIE, Deidre
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier 22-01-2001
• Subjects: Binding Sites; Biological and medical sciences; Bones, joints and connective tissue. Antiinflammatory agents; Carbohydrate Sequence; Drug Design; E-Selectin - drug effects; Humans; Inhibitory Concentration 50; Mannosides - chemical synthesis; Mannosides - metabolism; Mannosides - pharmacology; Medical sciences; Models, Molecular; Molecular Mimicry; Molecular Sequence Data; Oligosaccharides - chemical synthesis; Oligosaccharides - metabolism; Oligosaccharides - pharmacology; Pharmacology. Drug treatments; Protein Binding - drug effects; Structure-Activity Relationship; Carbohydrate antigen; Sialic acid; E Selectin; Antiinflammatory agent; Cell adhesion molecule; Modeling; Biological activity; Lewis system; α-Aminoacid; Biological fixation; Aminoglycoside; Molecular model; Dicarboxylic acid; Inhibitor; C-Glycoside; Chemical synthesis
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/s0960-894x(00)00623-5

The design and synthesis of novel beta-C-mannosides that inhibit the binding of sialyl Lewis x to E-selectin are described. Compounds that contained a phenyl substituent at the C-6 position were found to have increased potency.