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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents* / chemical synthesis
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Antineoplastic Agents* / chemistry
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Antineoplastic Agents* / pharmacology
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Cell Proliferation / drug effects
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Chalcones / chemical synthesis
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Chalcones / chemistry
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Chalcones / pharmacology*
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Drug Screening Assays, Antitumor
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Ferrous Compounds / chemical synthesis
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Ferrous Compounds / chemistry
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Ferrous Compounds / pharmacology*
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Glycosides / chemistry*
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HL-60 Cells
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Humans
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In Vitro Techniques
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Leukemia / drug therapy*
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Metallocenes
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Molecular Structure
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Pyrazoles / chemical synthesis
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Pyrazoles / chemistry
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Pyrazoles / pharmacology*
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Stereoisomerism
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Structure-Activity Relationship
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Tumor Cells, Cultured
Substances
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Antineoplastic Agents
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Chalcones
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Ferrous Compounds
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Glycosides
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Metallocenes
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Pyrazoles
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ferrocene