The neuropharmacological activity of two (–)-cytisine derivatives with adamantyl fragments was studied. It was shown that N-1-adamantylcytisine-12-thiocarbamide exhibited in tests in vivo a pronounced mnestic effect, increased the lifespan of laboratory animals under hypoxic conditions, and also enhanced in vitro binding of transcription factors NFAT and NF-κB to the DNA sequences corresponding to them.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
F. J. E. Vajda, J. Clin. Neurosci., 9, 4 (2002).
M. F. Beal, Ann. Neurol., 38, 357 (1995).
I. V. Damulin, Russ. Med. Zh., 9, No. 25, 1178 (2001).
W. Danysz, C. G. Parsons, and G. Quack, Amino Acids, 19, 167 (2000).
W. Danysz, C. G. Parsons, H.-J. Mobius, A. Stoffler, and G. Quack, Neurotoxic. Res., 2, 85 (2000).
G. Stamatiou, A. Kolocouris, N. Kolocouris, G. Fytas, G. B. Foscolos, J. Neyts, and E. De Clercq, Bioorg. Med. Chem. Lett., 11, 2137 (2001).
M.-J. Perez, J. Balzarini, M. Hosoya, E. De Clercq, and M.-J. Camarasa, Bioorg. Med. Chem. Lett., 2, 647 (1992).
N. Kolocouris, G. Zoidis, G. B. Foscolos, G. Fytas, S. R. Prathalingham, J. M. Kelly, L. Naesens, and E. De Clercq, Bioorg. Med. Chem. Lett., 17, 4358 (2007).
O. N. Zefirova, E. V. Nurieva, H. Lemcke, A. A. Ivanov, D. V. Shishov, D. G. Weiss, S. A. Kuznetsov, and N. S. Zefirov, Bioorg. Med. Chem. Lett., 18, 5091 (2008).
I. P. Tsypysheva, A. V. Kovalskaya, N. S. Makara, A. N. Lobov, I. A. Petrenko, E. G. Galkin, T. A. Sapozhnikova, F. S. Zarudii, and M. S. Yunuysov, Khim. Prir. Soedin., 565 (2012).
Handbook of Experimental (Preclinical) Study of New Drugs [in Russian], Moscow, 2005, 827 pp.
M. R. Muller and A. Rao, Nat. Rev. Immunol., 10, 645 (2010).
I. A. Kostanyan, A. V. Vonarshenko, and V. M. Lipkin, Bioorg. Khim., 36, 15 (2010).
M. S. Hayden and S. Ghosh, Genes Dev., 18, 2195 (2004).
G. L. Wang, B. H. Jiang, E. A. Rue, and G. L. Semenza, Proc. Natl. Acad. Sci. USA, 92, 5510 (1995).
APEX2 and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA, 2005.
G. M. Sheldrick, Acta Crystallogr. Sect. A: Found. Crystallogr., 64, 112 (2008).
F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor, J. Chem. Soc. Perkin Trans. 2, No. 2, 1 (1987).
Acknowledgment
The work was supported by a grant of the RFBR No. 12-03-00724-a, FTP “Science and Science-Pedagogical Departments of Innovation Russia” (Contract No. 8046) and the Basic Research Program of the RAS Presidium “Fundamental Sciences – Medicine” (Project Design and Synthesis of Potential Clinical Candidates for Treating Neurodegenerative Diseases, Injuries, and Neurotrauma Among (–)-Cytisine Derivatives) for 2013.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2013, pp. 606–609.
Rights and permissions
About this article
Cite this article
Tsypysheva, I.P., Koval′skaya, A.V., Lobov, A.N. et al. Synthesis and neuropharmacological activity of N-1-adamantylcytisine-12-carbamide and its 12-thiocarbonyl analog. Chem Nat Compd 49, 707–711 (2013). https://doi.org/10.1007/s10600-013-0713-y
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-013-0713-y