Enantiopure Sulforaphane Analogues with Various Substituents at the Sulfinyl Sulfur: Asymmetric Synthesis and Biological Activities

9 páginas, 4 figuras, 5 esquemas.
A convergent and high-yielding approach for the asymmetric synthesis of sulforaphane 2 and four analogues differently substituted at the sulfinyl sulfur has been developed. The key step of the synthesis is the diastereoselective synthesis of sulfinate ester 23-S(S), using the DAG (diacetone-D-glucofuranose)-methodology. The biological activity of these compounds as inductors of phase II detoxifying enzyme has been studied by determining their ability to activate the cytoprotective transcription factor Nrf2.
Financial support from the DGICyT (grant nos. CTQ2006-15515-CO2-01 and CTQ2007-61185) and the Junta de Andalucía (grants P06-FQM-01852 and P07-FQM-2774) is gratefully acknowledged. A.A. thanks the Ministerio de Ciencia e Innovación for a Ramón y Cajal contract. F.L. is supported by a predoctoral fellowship of the “Studienstiftung des Deutschen Volkes”.