Reductive alkylation of 3-amino-12-N-methylcytisine by aromatic aldehydes synthesized a series of secondary amines. The nootropic activity of the synthesized compounds was studied in vivo (mnestic and antihypoxic properties) and in vitro (antiradical properties and ability to affect transcription factor HIF-1 DNA-binding activity). The cytotoxicity of the synthesized compounds was assessed. The lead compound was identified.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
N. V. Titova, Russ. Med. Zh., 24, 1846 (2007).
T. A. Voronina, Farm. Toksikol., 54 (2), 6 (1991).
N. P. Shabalov, A. A. Skoromets, A. P. Shumilina, T. N. Platonova, Yu. V. Sereda, and O. A. Fedorov, Vestn. Ross. Voenno-med. Akad., 1 (5), 24 (2001).
M. Windisch, Brain Mechanisms and Psychotropic Drugs, CRC Press, New York, 1996, pp. 239–257.
T. A. Voronina and S. B. Seredenin, Eksp. Klin. Farmakol., 4, 3 (1998).
G. Semenza, Cell, 148 (3), 399 (2012).
Q. Ke and M. Costa, Mol. Pharmacol., 70 (5), 1469 (2006).
I. P. Tsypysheva, A. V. Koval'skaya, N. S. Makara, A. N. Lobov, I. A. Petrenko, E. G. Galkin, T. A. Sapozhnikova, F. S. Zarudii, and M. S. Yunusov, Chem. Nat. Compd., 48, 629 (2012).
Sh. B. Rakhimov, V. I. Vinogradova, Yu. R. Mirzaev, N. L. Vypova, and D. S. Kazantseva, Chem. Nat. Compd., 42, 462 (2006).
R. U. Khabriev, Handbook of Experimental (Preclinical) Study of New Drugs [in Russian], Meditsina, Moscow, 2005, 832 pp.
V. M. Berestovitskaya, O. S. Vasil'eva, B. M. Novikov, N. V. Usik, M. M. Zobacheva, I. N. Tjurenkov, V. N. Perfilova, and L. E. Borodkina, RU Pat. No. 2,216,322, Nov. 20, 2003.
T. A. Gudasheva, R. U. Ostrovskaya, S. S. Trofimov, M. Yu. Kosoi, F. V. Ienkina, Yu. V. Burov, and A. P. Soldinov, Khim.-farm. Zh., 19 (11), 1322 (1985).
T. J. Mosmann, Immunol. Methods, 65, 55 (1983).
C. Canu Boido and F. Sparatore, Il Farmaco, 54, 438 (1999).
K. Nagayama, A. Kumar, K. Wuthrich, and R. R. Ernst, J. Magn. Reson., 40, 321 (1980).
I. P. Tsypysheva, A. V. Koval’skaya, A. N. Lobov, M. Kh. Salimgareeva, U. Sh. Fatkullina, P. R. Petrova, S. F. Gabdrakhmanova, N. S. Makara, K. Yu. Suponitskii, Yu. V. Vakhitova, F. S. Zarudii, and M. S. Yunusov, Chem. Nat. Compd., 49, 707 (2013).
M. L. Belen'kii, Elements of Quantitative Assessment of the Pharmacological Effect [in Russian], Medgiz, Leningrad, 1963, 152 pp.
M. Kh. Salimgareeva, S. V. Sadovnikov, E. I. Farafontova, E. I. Zainullina, V. A. Vakhitov, and Yu. V. Vakhitova, Prikl. Biokhim. Mikrobiol., 50 (2), 219 (2014).
Acknowledgment
The work used equipment at the Biomika CCU (Department of Biochemical Research Methods and Nanobiotechnology, RTsKP Agidel, Ufa) and UNU KODINK. The work was sponsored by the RAS Presidium Basic Research Program “Basic Sciences – Medicine” for 2014; grants of the RF President for leading scientific schools NSh-5923.2014.4; and RFBR Grant No. 14-04-97035-povolzh'e-a.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2015, pp. 780–785.
Rights and permissions
About this article
Cite this article
Tsypysheva, I.P., Koval’skaya, A.V., Lobov, A.N. et al. Synthesis and Nootropic Activity of new 3-Amino-12-N-Methylcytisine Derivatives. Chem Nat Compd 51, 910–915 (2015). https://doi.org/10.1007/s10600-015-1446-x
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-015-1446-x