Bioactive 1,1′-unsymmetrical bi-functional ferrocenyl compounds using a novel solvent free one pot multicomponent reaction method

A solvent free synthetic method using rice husk ash (RHA) as solid support has been designed for selective functionalization and preparation of novel 1,1′- unsymmetrically bi-functionalized ferrocenyl compounds. The selectively functionalized intermediate compound, Ferrocenyl-1-acetyl-1′-thiosemicar...

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Bibliographic Details
Published in:Journal of organometallic chemistry 2020-02, Vol.908, p.121095, Article 121095
Main Authors: Barik, Tulasi, Ghosh, Avishek, Mishra, Abtar, Dhiman, Rohan, Sasamori, Takahiro, Chatterjee, Saurav
Format: Article
Language:English
Subjects:
Anticancer
Ferrocenyl
Rice husk ash
Solvent free
Unsymmetrical
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Summary:A solvent free synthetic method using rice husk ash (RHA) as solid support has been designed for selective functionalization and preparation of novel 1,1′- unsymmetrically bi-functionalized ferrocenyl compounds. The selectively functionalized intermediate compound, Ferrocenyl-1-acetyl-1′-thiosemicarbazone, has been structurally characterized using single crystal X-ray diffraction technique which revealed distinct inter-molecular hydrogen bonding interactions across the thiosemicarbazone chains. Cytotoxic evaluation of five different unsymmetrically bi-functionalized thiosemicarbazone - hydrazone compounds showed potent activity against human leukemia (THP-1) cell line. The unsymmetrical ferrocenyl compounds also showed strong BSA and DNA binding interactions and reversible redox properties. [Display omitted] •Selective functionalization of ferrocenyl Cp rings using rice husk ash (RHA) as solid support.•Solvent free multicomponent synthetic method for unsymmetrical functionalization of ferrocenyl derivatives.•Potent cytotoxicity for the unsymmetrically bi-functionalized thiosemicarbazone - hydrazone compounds.
ISSN:0022-328X
1872-8561
DOI:10.1016/j.jorganchem.2019.121095