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

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


Keywords


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

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