Issue 4, 2006
From the journal:

Dalton Transactions

Synthesis, structure and assessment of the cytotoxic properties of 2,5-dimethylazaferrocenyl phosphonates

Konrad Kowalski,ab   Janusz Zakrzewski,a   Nicholas J. Long,*b   Natsuko Suwaki,c   David J. Mannc  and  Andrew J. P. Whiteb  

* Corresponding authors

a Department of Organic Chemistry, Institute of Chemistry, University of Łódź, Narutowicza 68, Łódź, Poland

b Department of Chemistry, Imperial College London, South Kensington, London, UK
E-mail: n.long@imperial.ac.uk
Fax: +44 207 5945804
Tel: +44 207 5945781

c Division of Cell and Molecular Biology, Imperial College London, South Kensington, London, UK

Abstract

The reaction of lithiated 2,5-dimethylazaferrocene 1 with diethyl chlorophosphate proceeds to give lateral and ring phosphonate products. The products 2 and 3 were characterized by spectroscopic (1H, 31P{1H} NMR, MS, IR) methods and 3 was treated with W(CO)5(thf) to form a crystalline W(CO)5-complex 4 which was characterized by single-crystal X-ray analysis. The new 2,5-dimethylazaferrocenyl phosphonates were transformed into the corresponding N-methyl iodide salts 5 and 6 in quantitative yields. Both salts are water soluble and stable compounds and an analysis of their cytotoxic and anti-proliferative activity was carried out. Compound 6 possesses anti-metabolic activity which exhibited some preference towards the cancerous HeLa cell line over the non-cancerous NIH 3T3 cell line. These new compounds are the first examples of azaferrrocene (i.e. non-ferrocene) derivatives featuring biologically important phosphonate groups. The preliminary studies into cytotoxic activity indicates that as with ferrocene, azaferrocene can also be regarded as a potential source for organometallic anticancer agents, featuring the iron centre in the +2 oxidation state rather than the often utilized ferrocenium +3 species.

Graphical abstract: Synthesis, structure and assessment of the cytotoxic properties of 2,5-dimethylazaferrocenyl phosphonates

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Article information

DOI
https://doi.org/10.1039/B510445A
Article type
Paper
Submitted
21 Jul 2005
Accepted
04 Oct 2005
First published
26 Oct 2005

Dalton Trans., 2006, 571-576

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Synthesis, structure and assessment of the cytotoxic properties of 2,5-dimethylazaferrocenyl phosphonates

K. Kowalski, J. Zakrzewski, N. J. Long, N. Suwaki, D. J. Mann and A. J. P. White, Dalton Trans., 2006, 571 DOI: 10.1039/B510445A

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