Cyclic thioether peptide mimetics as VCAM-VLA-4 antagonists.
Selective substitution of a sulfur atom by carbon in a highly potent 13-membered cyclic disulfide was accomplished by intramolecular displacement of a bromide. The potency of the resulting thioethers in the VCAM/VLA-4 assay was dependent on ring size and the position of the sulfur atom.
Fotouhi
N
N
Roche Research Center, Hoffmann-La Roche Inc, Nutley, NJ 07110, USA. nader.fotouhi@roche.com
Joshi
P
P
Tilley
J W
JW
Rowan
K
K
Schwinge
V
V
Wolitzky
B
B
D039041:Integrin alpha4beta1; D016023:Integrins / Q000037:antagonists & inhibitors*; D018716:Molecular Mimicry; D010456:Peptides, Cyclic / Q000737:chemistry* / Q000494:pharmacology*; D016201:Receptors, Lymphocyte Homing / Q000037:antagonists & inhibitors*; D013440:Sulfides / Q000737:chemistry*; D019010:Vascular Cell Adhesion Molecule-1 / Q000187:drug effects*
D039041:Integrin alpha4beta1; D016023:Integrins; D010456:Peptides, Cyclic; D016201:Receptors, Lymphocyte Homing; D013440:Sulfides; D019010:Vascular Cell Adhesion Molecule-1