RESUMEN
A series of truncated analogs of α-galactosylceramide with altered ceramide moiety was prepared, and evaluated for Th2-biased response in the context of IL-4/IFN-γ ratio. Phytosphingosine-modified analogs including cyclic, aromatic and ethereal compounds as well as the C-glycoside analog of OCH (2) with their cytokine inducing profile are disclosed.
Asunto(s)
Galactosilceramidas/química , Galactosilceramidas/farmacología , Regulación de la Expresión Génica/efectos de los fármacos , Interferón gamma/metabolismo , Interleucina-4/metabolismo , Animales , Antígenos CD1d/química , Antígenos CD1d/metabolismo , Sitios de Unión , Simulación por Computador , Galactosilceramidas/síntesis química , Ratones , Ratones Endogámicos C57BL , Células Th2/efectos de los fármacosRESUMEN
The Lewis acid treatment of 2,3-epoxysulfonates with 2,3-dialkyl substituents or 2-alkyl-3-aryl substituents produced the rearrangement products via C3-cleavage of the oxirane ring in high yields. On the other hand, 2-aryl-3-alkyl-2,3-epoxysulfonates produced the products via C2-cleavage of the oxirane ring. The sulfonyloxy groups of the alpha-sulfonyloxy ketones, having a chiral benzylic quaternary carbon center obtained by the rearrangement of 2-alkyl-3-aryl-2,3-epoxysulfonates, were reductively eliminated to give the ketones with a chiral benzylic quaternary carbon center. The method was applied to the formal synthesis of (-)-aphanorphine and total syntheses of (-)-alpha-herbertenol and (-)-herbertenediol.
