REACTIVITY OF AZIRIDINE-2-CARBOXAMIDE (LEAKADINE) WITH NUCLEOPHILES IN AQUEOUS SOLUTIONS

Authors

  • R. Aleksis LOSI
  • K. Jaudzems LOSI
  • J. Ivanova LOSI
  • R. Žalubovskis LOSI
  • I. Kalvinsh LOSI
  • E. Liepiņš LOSI

DOI:

https://doi.org/10.1007/925

Keywords:

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

Abstract

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.

How to Cite
Aleksis, R.; Jaudzems, K.; Ivanova, J.; Žalubovskis, R. ; Kalvinsh, I.; Liepinsh, E. Chem. Heterocycl. Compd. 2014, 49, 1589. [Khim. Geterotsikl. Soedin. 2013, 1716.]

For this article in the English edition see DOI 10.1007/s10593-014-1410-x

Author Biographies

R. Aleksis, LOSI

Rihards Aleksis

K. Jaudzems, LOSI

Kristaps Jaudzems

J. Ivanova, LOSI

Jekaterina Ivanova

R. Žalubovskis, LOSI

Raivis Žalubovskis

I. Kalvinsh, LOSI

Ivars Kalvinsh

E. Liepiņš, LOSI

Edvards Liepiņš

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Published

2013-12-02

Issue

No. 11 (2013)

Section

Original Papers