ON DIFFERENCES BETWEEN RACEMIC AND ENANTIOMERICALLY PURE FORMS OF AZIRIDINE-2-CARBOXAMIDE

Authors

  • M. Turks Riga Technical University
  • I. Rijkure Riga Technical University
  • S. Belyakov Latvian Institute of Organic Synthesis
  • D. Zicāne Riga Technical University
  • V. Kumpiņš Riga Technical University
  • Ē. Bizdēna Riga Technical University
  • A. Meikas Institute for Gene Technology, Tallinn Technical University; Competence Center for Cancer Research
  • A. Valkna Institute for Gene Technology, Tallinn Technical University; Competence Center for Cancer Research

DOI:

https://doi.org/10.1007/1158

Keywords:

aziridine-2-carboxamide, chiral aziridines, Leakadine

Abstract

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.

Also published in Chemistry of Heterocyclic Compounds, 2012, 48 (6), pp 861-868

http://link.springer.com/article/10.1007/s10593-012-1067-2

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Published

2013-11-14

Issue

No. 6 (2012)

Section

Original Papers