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

Chemistry of Heterocyclic Compounds 2014
Rihards Aleksis, Kristaps Jaudzems, Jekaterīna Ivanova, Raivis Žalubovskis, Ivars Kalviņš, Edvards Liepiņš

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.

Atslēgas vārdi
aziridine-2-carboxamide; Leakadine; non-activated aziridines; nucleophilic ring opening
DOI
10.1007/s10593-014-1410-x
Hipersaite
http://link.springer.com/article/10.1007/s10593-014-1410-x

Aleksis, R., Jaudzems, K., Ivanova, J., Žalubovskis, R., Kalviņš, I., Liepiņš, E. Reactivity of Aziridine-2-Carboxamide (Leakadine) with Nucleophiles in Aqueous Solutions. Chemistry of Heterocyclic Compounds, 2014, Vol.49, No.11, 1589.-1598.lpp. ISSN 0009-3122. e-ISSN 1573-8353. Pieejams: doi:10.1007/s10593-014-1410-x

Publikācijas valoda
English (en)