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On differences between racemic and enantiomerically pure forms of aziridine-2-carboxamide*

Synthesis, X-ray, and cytotoxicity studies of (S)- and (R)-aziridine-2-carboxamide (Leakadine) are described. X-ray data for the enantiomerically pure form are compared with those for racemic aziridine-2-carboxamide in order to explain the 21°C large melting point difference between both series. It was found that despite their overall low cytotoxicity (S)-aziridine-2-carboxamide is slightly more cytotoxic than (R)-aziridine-2-carboxamide.

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Correspondence to M. Turks.

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*Dedicated to Professor Ivars Kalvinsh on the occasion of his 65th birthday.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 928-935, May, 2012.

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Turks, M., Rijkure, I., Belyakov, S. et al. On differences between racemic and enantiomerically pure forms of aziridine-2-carboxamide*. Chem Heterocycl Comp 48, 861–868 (2012). https://doi.org/10.1007/s10593-012-1067-2

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Keywords

  • aziridine-2-carboxamide
  • chiral aziridines
  • Leakadine