ABSTRACT
A highly diastereo- and enantioselective Mannich-type reaction of azlactones with aldimines catalyzed by a chiral phosphoric acid is described. Only 3 mol % catalyst was required to prepare the Mannich adducts in good yields with high stereochemical control (up to >19:1 dr, >99:1 er). Moreover, the final product contains two consecutive stereogenic centers, one of which is quaternary.
Subject(s)
Imines/chemistry , Lactones/chemistry , Phosphoric Acids/chemistry , Catalysis , Crystallography, X-Ray , Models, Molecular , Molecular Structure , StereoisomerismABSTRACT
The isoflavone genistein 1 and some derivatives modulate IL-12, TNF-α and NO production by macrophages and lung cancer cell lines, and improve the clinical signs of experimental autoimmune encephalomyelitis (EAE). Seven genistein derivatives connected at C-6 position of a sugar, such as d-glucose and d-galactose, were synthesized. The ability to modulate macrophage response was evaluated, showing variable inhibition capacity of NO and TNF-α production in J774.A1 and RAW 264.7. Five of the seven compounds were non-cytotoxic; compound 8 was more effective to inhibit NO and TNF-α production, without affecting cell viability.
