The first oxalamide‐bridged ferrocene: Facile synthesis, preliminary conformational analysis and biological evaluation

tert‐Butyl‐1′‐methoxycarbonyl‐1‐ferrocenecarbamate (1) was Boc‐deprotected to give free amine which underwent oxalyl chloride‐mediated dimerization. The structure of the so‐obtained oxalamide‐bridged ferrocene 2 was elucidated using infrared and NMR (1H, 13C, COSY, NOESY, HSQC, HMBC) spectroscopies,...

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Bibliographic Details
Published in:Applied organometallic chemistry 2017-07, Vol.31 (7), p.n/a
Main Authors: Kovač, Veronika, Radošević, Kristina, Bebek, Anica, Makarević, Janja, Štefanić, Zoran, Barišić, Lidija, Žinić, Mladen, Rapić, Vladimir
Format: Article
Language:English
Subjects:
Biological activity
Biotechnology
Chemistry
Conformational analysis
Crystal structure
Cytotoxicity
Dimerization
dual biological activity
ferrocene
High resolution
hydrogen bond
Hydrogen bonding
In vitro methods and tests
Infrared spectroscopy
Ionization
Ions
Mass spectrometry
NMR
Nuclear magnetic resonance
oxalamide
Single crystals
Structural analysis
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Summary:tert‐Butyl‐1′‐methoxycarbonyl‐1‐ferrocenecarbamate (1) was Boc‐deprotected to give free amine which underwent oxalyl chloride‐mediated dimerization. The structure of the so‐obtained oxalamide‐bridged ferrocene 2 was elucidated using infrared and NMR (1H, 13C, COSY, NOESY, HSQC, HMBC) spectroscopies, crystal structure analysis, and electrospray ionization and high‐resolution mass spectrometry. The preliminary conformational analysis in solution suggested the intramolecular engagement of oxalamide protons, while single‐crystal analysis revealed an 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 effects of the tested compound in the applied concentration range (1–350 μM) on HEK293T and HepG2 cells. Stimulatory effect on cell growth was the most pronounced for normal HEK293T cells, while the highest cytotoxic effect was observed towards HeLa tumour cells and it was dose‐dependent. The observed dual biological activity of 2 implies its potential application in drug development. In vitro screening of a novel oxalamide‐bridged ferrocene revealed the most pronounced proliferative effect for normal HEK293T cells, whilst the cytotoxic activity was the highest for tumour HeLa cells.
ISSN:0268-2605
1099-0739
DOI:10.1002/aoc.3653