METHOD FOR THE PREPARATION OF 4-ARYL-3-PYRROLIN-2-ONES AND THEIR 5-BROMO DERIVATIVES

Authors

  • М. Ворона Latvian Institute of Organic Synthesis
  • Н. Орлова Latvian Institute of Organic Synthesis
  • Е. Кузнецов Latvian Institute of Organic Synthesis
  • С. Викайнис Latvian Institute of Organic Synthesis
  • Э. Лиепиньш Latvian Institute of Organic Synthesis
  • С. Беляков Latvian Institute of Organic Synthesis
  • А. Мишнев Latvian Institute of Organic Synthesis
  • Г. Вейнберг Latvian Institute of Organic Synthesis

DOI:

https://doi.org/10.1007/382

Keywords:

aziridines, aziridine-triazole conjugates, triazoles, anticancer drugs, azide-alkyne dipolar cycloaddition, MMP-2 inhibitors

Abstract

A series of (aryltriazolyl)methylaziridines was 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 metalloproteinase-2 at 73% in 20 μM concentration and at 75% in 10 μM concentration, respectively.

Authors: M. Vorona, N. Orlova, E. Kuznetsov, S. Vikainis, E. Liepinsh, S. Belyakov, A. Mishnev, G. Veinberg.

English Translation in Chemistry of Heterocyclic Compounds, 2013, 49 (8), pp 1118-1127

http://link.springer.com/article/10.1007/s10593-013-1352-8

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Published

2013-06-17

Issue

No. 8 (2013)

Section

Original Papers