Abstract
Formylation of ansa[4]-ferrocene, obtained through the ruthenium-catalysed olefin metathesis, yields two separable, planar chiral 1,3- and 1,2-ansa-ferrocene aldehydes. Single-crystal X-ray structure analysis reveals that both regioisomers crystallize with spontaneous resolution of the racemate in the chiral P212121 space group with one molecule in the asymmetric unit. The major 1,3-isomer was further transformed into a conjugate with 1,2,3-triazole and uracil using "click" chemistry as the key synthetic step. This inorganic-organic hybrid displays anticancer activity (MCF-7, A549, MDA-MB-231 cell lines) with EC50 values comparable to those for cisplatin.
MeSH terms
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Aldehydes / chemistry
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Alkenes / chemistry
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / pharmacology
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Apoptosis / drug effects
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Catalysis
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Cell Line, Tumor
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Cell Proliferation / drug effects
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Click Chemistry
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Coordination Complexes / chemical synthesis*
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Coordination Complexes / pharmacology
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Drug Development
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Ferrous Compounds / chemical synthesis*
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Ferrous Compounds / pharmacology
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Humans
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Isomerism
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Metallocenes / chemical synthesis*
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Metallocenes / pharmacology
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Ruthenium / chemistry
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Structure-Activity Relationship
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Triazoles / chemistry
Substances
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Aldehydes
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Alkenes
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Antineoplastic Agents
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Coordination Complexes
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Ferrous Compounds
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Metallocenes
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Triazoles
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Ruthenium
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ferrocene