Synthesis of cytotoxic ferrocenyl flavones via a ferricenium-mediated 1,6-oxidative cyclization

The oxidation of the ferrocenyl group of 2'-hydroxyferrocenyl chalcones activates the beta-position of the unsaturated ketone to nucleophilic attack to yield the first examples of ferrocenyl flavones. These compounds are significantly more cytotoxic than their organic analogs on B16 melanoma ce...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2010-01, Vol.46 (28), p.5145-5147
Main Authors: Monserrat, Jean-Philippe, Chabot, Guy G, Hamon, Louis, Quentin, Lionel, Scherman, Daniel, Jaouen, Gérard, Hillard, Elizabeth A
Format: Article
Language:English
Subjects:
Analogs
Animals
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - therapeutic use
Chalcones - chemical synthesis
Chalcones - chemistry
Chalcones - therapeutic use
Chemical attack
Cyclization
Ferrous Compounds - chemistry
Flavones - chemistry
Flavones - therapeutic use
Flavones - toxicity
Ketones
Melanoma, Experimental - drug therapy
Metallocenes
Mice
Oxidation
Oxidation-Reduction
Synthesis
Unsaturated
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Summary:The oxidation of the ferrocenyl group of 2'-hydroxyferrocenyl chalcones activates the beta-position of the unsaturated ketone to nucleophilic attack to yield the first examples of ferrocenyl flavones. These compounds are significantly more cytotoxic than their organic analogs on B16 melanoma cells, with IC(50) values in the low micromolar range.
ISSN:1359-7345
1364-548X
DOI:10.1039/c0cc01290d