Design and synthesis of sialyl Lewis x mimics as E-selectin inhibitors.
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.
Kaila
N
N
Department of Chemical Sciences, Wyeth Research, Cambridge, MA 02140, USA. nkaila@genetics.com
Thomas
B E
BE
Thakker
P
P
Alvarez
J C
JC
Camphausen
R T
RT
Crommie
D
D
D001665:Binding Sites; D002240:Carbohydrate Sequence; D015195:Drug Design; D019040:E-Selectin / Q000187:drug effects*; D006801:Humans; D020128:Inhibitory Concentration 50; D008362:Mannosides / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology; D008958:Models, Molecular; D018716:Molecular Mimicry; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology*; D011485:Protein Binding / Q000187:drug effects; D000080506:Sialyl Lewis X Antigen; D013329:Structure-Activity Relationship
D019040:E-Selectin; D008362:Mannosides; D009844:Oligosaccharides; D000080506:Sialyl Lewis X Antigen