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Synthesis, Structure, and in vitro Antitumor Activity of Some Glycoside Derivatives of Ferrocenyl‐Chalcones and Ferrocenyl‐Pyrazolines
Author(s) -
ZsoldosMády Virág,
Csámpai Antal,
Szabó Rita,
MészárosAlapi Erika,
Pásztor Judit,
Hudecz Ferenc,
Sohár Pál
Publication year - 2006
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.200600052
Subject(s) - chemistry , chalcone , pyrazole , pyrazoline , in vitro , glycoside , reagent , hydrazine (antidepressant) , stereochemistry , benzaldehyde , structural isomer , molecule , combinatorial chemistry , medicinal chemistry , organic chemistry , biochemistry , catalysis
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.