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

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• 作者：Piotr Kie艂basi艅ski^a ; ^{piokiel@cbmm.lodz.pl" class="auth_mail} ; Jerzy 艁uczak^a ; Tomasz Cierpia艂^a ; Jaros艂aw B艂aszczyk^a ; Les艂aw Siero艅^b ; Katarzyna Wiktorska^c ; ^{k.wiktorska@nil.gov.pl" class="auth_mail} ; Katarzyna Lubelska^c ; Ma艂gorzata Milczarek^c ; Zdzis艂aw Chilmo艅czyk^c
• 关键词：Sulforaphane ; Isothiocyanates ; Sulfoxides ; Organofluorine compounds ; Melanoma
• 刊名：European Journal of Medicinal Chemistry
• 出版年：9 April, 2014
• 年：2014
• 卷：76
• 期：Complete
• 页码：332-342
• 全文大小：1715 K

文摘

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聽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.