Synthesis and Cytotoxicity of 2,3-Enopyranosyl C-Linked Conjugates of Genistein

Molecules

Wieslaw Szeja²  Grzegorz Grynkiewicz¹  Tadeusz Bieg²  Piotr Swierk²  Anna Byczek²  Katarzyna Papaj²  Radosᐪw Kitel² 

[1]Pharmaceutical Research Institute, Rydygiera 8, 01-793 Warsaw, Poland

[2] E-Mail:

[3]Department of Chemistry, Biochemistry and Biotechnology, Silesian Technical University, Krzywoustego 8, 44-100 Gliwice, Poland

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关键词: l-rhamnal;    C-glycosylation;    genistein conjugates;    cell cycle;   

DOI  :  10.3390/molecules19067072

来源: mdpi

【 摘 要 】

A series of glycoconjugates, derivatives of genistein containing a C-glycosylated carbohydrate moiety, were synthesized and their anticancer activity was tested in vitro in the human cell lines HCT 116 and DU 145. The target compounds 15–17 were synthesized by treating ω-bromoalkyl C-glycosides derived from l-rhamnal (1) with a tetrabutylammonium salt of genistein. The new, metabolically stable analogs of previously studied O-glycosidic genistein derivatives inhibited proliferation of cancer cell lines through inhibition of the cell cycle.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.