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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F. M. D. Ismail, D. O. Levitsky, and V. M. Dembitsky, Eur. J. Med. Chem., 44, 3373 (2009).
J. B. Sweeney, Chem. Soc. Rev., 31, 247 (2002).
Y. Nakao, M. Fujita, K. Warabi, S. Matsunaga, and N. Fusetani, J. Am. Chem. Soc., 122, 10462 (2000).
R. S. Coleman and J. Li, A. Navarro, Angew. Chem., Int. Ed., 40, 1736 (2001).
B. S. Iyengar, R. T. Dorr, and W. A. Remers, J. Med. Chem., 47, 218 (2004).
B. S. Iyengar, R. T. Dorr, D. S. Alberts, E. M. Hersh, S. E. Salmon, and W. A. Remers, J. Med. Chem., 42, 510 (1999).
I. Ya. Kalvinsh and E. B. Astapenok, Belg. Pat. Appl. 860239; Chem. Abstr., 90, 34103 (1979).
I. Y. Kalvinsh and E. B. Astapenok, US Pat. Appl. 4686215; Chem. Abstr., 107, 168799 (1987).
P. Trapencieris, I. Kalviņš, L. Kauliņa, and V. Kauss, Org. Process Res. Dev., 1, 259 (1997).
P. J. A. Kuehl and W. A. Remers, WO Pat. Appl. 2008045686; Chem. Abstr., 148, 456463 (2008).
A. Fürst, E. Kyburz, and S. Majnoni, Swiss Pat. Appl. 362078; Chem. Abstr., 59, 62128 (1963).
K. Nakajima, F. Takai, T. Tanaka, and K. Okawa, Bull. Chem. Soc. Jpn., 51, 1577 (1978).
K. Jähnisch, E. Gründemann, A. Kunath, and M. Ramm, Liebigs Ann. Chem., 881 (1994).
J. E. Baldwin, A. C. Spivey, C. J. Schofield, and J. B. Sweeney, Tetrahedron, 49, 6309 (1993).
H. Harada, T. Morie, T. Suzuki, T. Yoshida, and S. Kato, Tetrahedron, 54, 10671 (1998).
G. E. Veitch, K. L. Bridgwood, and S. V. Ley, Org. Lett., 10, 3623 (2008).
M. Turks, D. Zicāne, and I. Rijkure, LV Pat. Appl. 13848; Chem. Abstr., 151, 490989 (2009).
P. T. Trapentsier, I. Ya. Kalvin’sh, E. E. Liepin’sh, and E. Ya. Lukevits, Khim. Geterotsikl. Soedin., 350 (1983). [Chem. Heterocycl. Compd., 19, 283 (1983)].
T. Mosmann, J. Immunol. Methods, 65, 55 (1983).
A. A. Starchenko, V. A. Khil'ko, S. A. Komarets, A. N. Khlunovskii, T. I. Prilukova, S. V. Kraskovskaia, and A. V. Danilov, Zh. Vopr. Neirokhir. im. N. N. Burdenko, 15 (1996).
H. E. Gottlieb, V. Kotlyar, and A. Nudelman, J. Org. Chem., 62, 7512 (1997).
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, and R. Spagna, J. Appl. Cryst., 32, 115 (1999).
G. M. Sheldrick, SHELXL-97. Program for the Refinement of Crystal Structures, University of Göttingen, Göttingen, 1997.
S. Mackay, C. J. Gilmore, C. Edwards, N. Stewart, and K. Shankland, maXus. Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow, 1999.
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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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DOI: https://doi.org/10.1007/s10593-012-1067-2