New enantiomeric fluorine-containing derivatives of sulforaphane: Synthesis, absolute configurations and biological activity

• The first synthesis of fluorine-containing derivatives of sulforaphane.
• Each derivative has been obtained in enantiomerically pure forms.
• Absolute configuration of each enantiomer has been determined by X-ray and CD.
• In vitro tests revealed their enhanced activity against melanoma.

Three pairs of enantiomers of the unknown sulforaphane analogs bearing organofluorine substituents bonded to the sulfinyl sulfur atom and having different number of methylene groups in the central carbon chain were synthesized and fully characterized, including determination of their absolute configurations. All the new compounds were tested in vitro for their cytotoxicity against melanoma cells to show increased activity in comparison with the natural sulforaphane. The influence of the particular structural changes in the molecule on the cytotoxicity is discussed.

New enantiomeric fluorine-containing derivatives of sulforaphane: synthesis, absolute configurations and biological activity, Piotr Kiełbasiński, Jerzy Łuczak, Tomasz Cierpiał, Jarosław Błaszczyk, Lesław Sieroń, Katarzyna Wiktorska, Katarzyna Lubelska, Małgorzata Milczarek, and Zdzisław Chilmończyk, European Journal of Medicinal Chemistry.Figure optionsDownload as PowerPoint slide