ISBN: 978-83-60043-10-3 - eurobic9

Eurobic9, 2-6 September, 2008, Wrocław, Poland
I. P. Lorenz
P115. Aziridines: Coordination Chemistry And Biological Activity
Ludwig-Maximilians-University of Munich, Department of Chemistry and Biochemistry, Butenandtstr. 9-13,
81377 Munich, Germany
e-mail: ipl@cup.uni-muenchen.de
Aziridines, the three-membered N-heterocycles, are important not only as synthetic tools in organic chemistry.
Compounds with aziridine mojeties show cytostatic, cytotoxic and mutagene activity. The family of
mitomycines, for instance, are used in the chemotherapy of cancer deseases. Their mode of action is assumed to
the strained ring structure which is opened enzymatically resulting in the methylation of DNA-tumor cells.
Aziridine complexes may also possess therapeutic applications, which is the reason we investigate in detail the
coordination chemistry of aziridines and their metal-induced or metal-mediated reactions.
Our results demonstrate that aziridines are not only useful as ligands for transition metals yielding mono-, bis,
tris- and tetrakis-aziridine complexes.
Aziridines are also versatile and active ligands which lead to compounds with different functionalities. In special
cases aziridines react via single C-N-opening reaction with co-ligands (like CO or itself) to give e. g.
β-aminoacyl complexes, heterocyclic carbene complexes or β-aminoaziridine complexes. The last hitherto
unknown N, N’-chelate is the formal dimer of aziridine and can be separated from the metal and isolated;
especially its Cu(II) complex is highly cytotoxic. Rh(I) and Ir(I) complexes with this N, N’-chelate undergo an
oxidative addition reaction after a second C-N-opening reaction to yield the new tridentate ligand
(N-aminoethyl)-2-amidoethyl with two M-N and one M-C bonds.
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