Spin-labeled cytisine derivatives containing stable pyrrolidine and piperidine nitroxyl radicals were synthesized by acylation and alkylation of the secondary amine. Toxicological studies showed that introduction of the nitroxyl group decreased significantly the general toxicity.
Similar content being viewed by others
References
Z. D. Raikov, E. T. Raikova, and A. T. Atanasov, Med. Hypotheses, 57, 302 (2001); J. Russel, N. Okayama, J. S. Alexander, D. N. Granger, and C. J. Hsia, Free Radical Biol. Med., 25, 153 (1998); P. Seminara, F. Franchi, N. Konovalova, C. Pioli, R. Rossetti, L. Tubani, G. Doria, and F. R. Fanelli, Acta Haematol., 105, 77 (2001); J. Skolimowski, A. Kochman, L. Cebicka, and D. Metodiewa, Bioorg. Med. Chem., 11, 3529 (2003).
P. Tutka and W. Zatonski, Pharmacol. Rep., 58, 777 (2006).
A. P. Kozikowski, S. K. Chellappan, Y. Xiao, K. M. Bajjuri, H. Yuan, K. J. Kellar, and P. A. Petukhov, Chem. Med. Chem., 2, 1157 (2007).
E. G. Perez, C. Mendez-Galvez, and B. K. Cassels, Nat. Prod. Rep., 29, 555 (2012).
M. S. Frasinyuk, V. I. Vinogradova, S. P. Bondarenko, and V. P. Khilya, Chem. Nat. Compd., 43, 590 (2007).
S. P. Bondarenko, M. S. Frasinyuk, V. I. Vinogradova, and V. P. Khilya, Chem. Nat. Compd., 46, 771 (2010).
S. P. Bondarenko, M. S. Frasinyuk, V. I. Vinogradova, and V. P. Khilya, Chem. Nat. Compd., 47, 604 (2011).
V. A. Saprykina, V. I. Vinogradova, R. F. Ambartsumova, T. F. Ibragimov, and Kh. M. Sakhidoyatov, Chem. Nat. Compd., 42, 470 (2006).
A. K. Przybyl and M. Kubicki, J. Mol. Struct., 985, 157 (2011).
I. V. Kulakov, D. M. Turdybekov, Z. M. Zhambekov, O. A. Nurkenov, B. T. Ibragimov, S. A. Talipov, and K. M. Turdybekov, Khim. Prir. Soedin., 572 (2009).
L. B. Volodarskii, I. A. Grigorev, S. A. Dikanov, V. A. Reznikov, and G. I. Shchukin, Imidazoline Nitroxyl Radicals [in Russian], Nauka, Novosibirsk, Sib. Br., 1988, 216 pp.
M. Niks and M. Otto, J. Immunol. Methods, 130, 149 (1990).
L. Berliner (ed.), Spin Labeling/ 1., Academic Press, New York, 1976.
S. Ogawa and H. M. McConnel, Proc. Natl. Acad. Sci. USA, 58, 19 (1967).
H. O. Hankovszky, K. Hideg, and J. Tigyi, Acta Chim. Acad. Sci. Hung., 98, 339 (1978).
Acknowledgment
The work was supported financially by RFBR Grant No. 12-03-00718a and the Moscow Administration Program (Contract No. 16-12-Gen-M). Spectral characteristics and XSA data of the synthesized compounds were obtained at the Chemical Service, CCH, SB, RAS.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Prirodnykh Soedinenii, No. 2, March–April, 2013, pp. 264–267.
Rights and permissions
About this article
Cite this article
Polienko, Y.F., Vinogradova, V.I., Sagdullaev, S.S. et al. First spin-labeled cytisine derivatives. Chem Nat Compd 49, 311–315 (2013). https://doi.org/10.1007/s10600-013-0588-y
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-013-0588-y