1061602-02-5Relevant articles and documents
Unexpected reaction of 2-alkylsulfanylimidazoles to imidazol-2-ones: Pyridinylimidazol-2-ones as novel potent P38α mitogen-activated protein kinase inhibitors
Koch, Pierre,Laufer, Stefan
scheme or table, p. 4798 - 4802 (2010/10/03)
While optimizing the synthesis of 2-alkylsulfanyl-5-(2-aminopyridin-4-yl) imidazoles, we identified an unexpected reaction to pyridinylimidazol-2-ones. 2-Alkylsulfanylimidazoles, bearing a 2-hydroxyethyl or a 2,3-dihydroxypropyl moiety at the imidazole C2-S position, were converted by heating into imidazol-2-ones. These imidazol-2-ones were tested for their ability to inhibit p38α MAP kinase and LPS-stimulated TNF-α release in HWB. Introduction of an amino moiety at the pyridine C2 position led to compounds showing potent enzyme inhibitory activity with double-digit nanomolar IC 50 values (5a: IC50 = 23 nM).