Ferrocenyl chalcogeno (sugar) triazole conjugates: Synthesis, characterization and anticancer properties

• We report the first synthesis and characterization of monosubstituted ferrocenyl chalcogen (S/Se) propargyl ligand.
• 1,3-Huisgen coupling reaction of the alkyne with different azides yielded the triazole derivatives.
• The electronic and electrochemical studies of the new ferrocene sugar conjugates are described.
• Anticancer properties against a panel of five cell lines studied.

This article describes the synthesis, characterization and anticancer properties of a series of chalcogeno (S/Se) triazole bridged ferrocene-carbohydrate conjugates. The alkyne, ferrocenyl chalcogeno propargyl, was prepared from the reaction of in situ generated ferrocenyl chalcogenide anion and propargyl bromide. The corresponding sugar triazoles were prepared from the Huisgen coupling of the ferrocenyl chalcogen propargyls with the respective sugar azides. Benzyl triazole (4a, b(i)) was synthesized for the comparison purpose and the structure was determined using a single crystal X-ray diffraction study. UV–visible spectroscopy and electrochemical studies were performed on triazole conjugates. Furthermore, the ferrocenyl chalcogeno triazole conjugates exhibited significant cytotoxicity against different cancer cell line with an IC50 value lower than 20 μM and the lowest IC50 value of 2.9 μM was exhibited by the ferrocenyl selenoribose triazole conjugate.

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