Synthesis, Structure, and in vitro Antitumor Activity of Some Glycoside Derivatives of Ferrocenyl-Chalcones and Ferrocenyl-Pyrazolines

✍ Scribed by Virág Zsoldos-Mády; Antal Csámpai; Rita Szabó; Erika Mészáros-Alapi; Judit Pásztor; Ferenc Hudecz; Pál Sohár

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 133 KB
• Volume: 1
• Category: Article
• ISSN: 1860-7179
• DOI: 10.1002/cmdc.200600052

✦ Synopsis

Abstract

Some new glycosides of 3‐ferrocenyl‐1‐(4′‐hydroxyphenyl)‐prop‐2‐en‐1‐one were prepared and transformed into the corresponding pyrazoline and pyrazole derivatives. Using methyl‐hydrazine, formation of regioisomers was observed. DDQ was found to be a mild and efficient reagent for the pyrazoline‐pyrazole dehydroaromatization process. The structure of the new compounds was proved by IR and NMR spectroscopy. The in vitro antitumor activity of the substances was investigated against human leukemia (HL‐60) cells by the MTT method. Among these new compounds some chalcone derivatives (3 a, 3 b, 5 a, and 5 b) showed attractive in vitro antitumor effects on human leukemia cells. These molecules contained ferrocenyl moieties and a p‐hydroxy‐phenolic ring or a size‐independent apolar substitution of that.