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Chemistry of Heterocyclic Compounds

, Volume 49, Issue 11, pp 1589–1598 | Cite as

Reactivity of Aziridine-2-Carboxamide (Leakadine) with Nucleophiles in Aqueous Solutions*

  • R. Aleksis
  • K. Jaudzems
  • J. Ivanova
  • R. Žalubovskis
  • I. Kalvinsh
  • E. LiepinshEmail author
Article

We describe studies of aziridine-2-carboxamide (Leakadine) reactivity with N-, O-, and S-nucleophiles in aqueous solutions using NMR spectroscopy and chemical synthesis. The results show that nucleophilic ring opening reactions of Leakadine with N- and O-nucleophiles take place only in acidic solutions, while reactions with S-nucleophiles occur irrespective of the pH and at a significantly higher reaction rate. These data suggest that the antitumor and immunostimulating activity of Leakadine may be associated with inhibition of extracellular cysteine proteases of cancer cells.

Keywords

aziridine-2-carboxamide Leakadine non-activated aziridines nucleophilic ring opening 

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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • R. Aleksis
    • 1
  • K. Jaudzems
    • 1
  • J. Ivanova
    • 1
  • R. Žalubovskis
    • 1
  • I. Kalvinsh
    • 1
  • E. Liepinsh
    • 1
    Email author
  1. 1.Latvian Institute of Organic SynthesisRigaLatvia

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