Discovery of Aziridine–Triazole Conjugates as Selective MMP-2 Inhibitors

Chemistry of Heterocyclic Compounds 2013
Imants Kreituss, Elīna Rozenberga, Jānis Zemītis, Peteris Trapencieris, Nadezhda Romanchikova, Māris Turks

A series of (aryltriazolyl)methylaziridines were synthesized and evaluated as selective inhibitors of matrix metalloproteinase-2. They constitute a novel class of hydroxamic acid-free matrix metalloproteinase inhibitors. The triazole fragment serves as a linker between the hydrophilic aziridine and the lipophilic part of the molecule. The best inhibition was observed with 1-(aziridin-2-ylmethyl)-4-(4-butylphenyl)-1H-1,2,3-triazole and 1-(aziridin-2-ylmethyl)-4-phenyl-1H-1,2,3-triazole that selectively inhibited MMP-2 at 73% in 20 μM concentration and at 75% in 10 μM concentration, respectively.

Keywords
aziridines, aziridine–triazole conjugates, triazoles, anticancer drugs, azide-alkyne dipolar cycloaddition, MMP-2 inhibitors
DOI
10.1007/s10593-013-1351-9
Hyperlink
http://link.springer.com/article/10.1007%2Fs10593-013-1351-9

Kreituss, I., Rozenberga, E., Zemītis, J., Trapencieris, P., Romanchikova, N., Turks, M. Discovery of Aziridine–Triazole Conjugates as Selective MMP-2 Inhibitors. Chemistry of Heterocyclic Compounds, 2013, Vol.49, Iss.8, pp.1191-1200. ISSN 0009-3122. Available from: doi:10.1007/s10593-013-1351-9

Publication language
English (en)