Amino-substituted heterocycles as isosteres of trans-cinnamides: design and synthesis of heterocyclic biaryl sulfides as potent antagonists of LFA-1/ICAM-1 binding

GT Wang, S Wang, R Gentles, T Sowin, S Leitza…

Index: Wang, Gary T.; Wang, Sheldon; Gentles, Robert; Sowin, Thomas; Leitza, Sandra; Reilly, Edward B.; Von Geldern, Thomas W. Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 1 p. 195 - 201

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Citation Number: 20

Abstract

2-Amino-4-phenyl pyridine and, to a lesser extent, 4-amino-6-phenyl pyrimidine, were established as isosteres of trans-cinnamide moiety. Applying this isosterism to previously reported p-arylthio cinnamides resulted in the identification of 4-amino-6-(p-arylthio) phenyl- pyrimidines and 2-amino-4-(p-arylthio) phenyl-pyridines as potent antagonists of LFA- 1/ICAM-1 binding.