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The first oxalamide-bridged ferrocene : facile synthesis, preliminary conformational analysis and biological evaluation

The tert-butyl 1'-methoxycarbonyl-1-ferrocenecarbamate (1) was Boc-deprotected to give free amine which underwent oxalyl chloride mediated dimerization. The structure of so-obtained oxalamide-bridged ferrocene 2 was elucidated by IR and NMR (1H, 13C, COSY, NOESY, HSQC, HMBC) spectroscopy, crystal structure analysis, ESI-MS and HRMS. The preliminary conformational analysis in solution suggested the intramolecular engagement of oxalamide protons, while single crystal analysis revealed the intermolecular hydrogen-bonding pattern. Also, the effect of oxalamide-bridged ferrocene 2 on cell viability of three human cell lines (HEK293T, HeLa and HepG2) was tested. In vitro screening revealed proliferative as well as cytotoxic effect of the tested compound in applied concentration range (1 µM - 350 µM) on HEK293T and HepG2 cells. Stimulatory effect on cell growth was the most pronounced on normal HEK293T cells, while the highest cytotoxic effect was observed toward tumour HeLa cells and it was dose-dependent. The observed dual biological activity of oxalamide-bridged ferrocene 2 implies its potential application in drug development.

Ferrocene ; Oxalamide ; Crystal structure ; Citotoxicity

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