Synthesis, structure, and in vitro antitumor activity of some glycoside derivatives of ferrocenyl-chalcones and ferrocenyl-pyrazolines.
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.
Zsoldos-Mády
Virág
V
Research Group for Structural Chemistry and Spectroscopy, Hungarian Academy of Sciences-Eötvös Loránd University, Pázmány Sétány 1A, Budapest, Hungary.
Csámpai
Antal
A
Szabó
Rita
R
Mészáros-Alapi
Erika
E
Pásztor
Judit
J
Hudecz
Ferenc
F
Sohár
Pál
P
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D049109:Cell Proliferation / Q000187:drug effects; D047188:Chalcones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D005296:Ferrous Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006027:Glycosides / Q000737:chemistry*; D018922:HL-60 Cells; D006801:Humans; D066298:In Vitro Techniques; D007938:Leukemia / Q000188:drug therapy*; D000075163:Metallocenes; D015394:Molecular Structure; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D047188:Chalcones; D005296:Ferrous Compounds; D006027:Glycosides; D000075163:Metallocenes; D011720:Pyrazoles; C004998:ferrocene