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Enantiopure Sulforaphane Analogues with Various Substituents at the Sulfinyl Sulfur: Asymmetric Synthesis and Biological Activities
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2009
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Bioorganic ChemistryEngineeringMolecular BiologyOrganic ChemistryChemistryEnantiopure Sulforaphane AnaloguesChemical BiologySulfinyl SulfurMedicinal ChemistryBiosynthesisNatural Product BiosynthesisStereoselective SynthesisBiochemistryBiocatalysisAsymmetric SynthesisNatural Product SynthesisPharmacologyAsymmetric CatalysisEnantioselective SynthesisBiomolecular EngineeringNatural SciencesSulfinate EsterSulforaphane 2Synthetic Chemistry
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.