Abstract
Using the acylation reaction with tosyl chloride of N-aminopropyl analogues of tacrine and its cyclic homologues with different size of the aliphatic cycle (5–8), we synthesized a number of new derivatives of p-toluenesulfonamide. It is shown that the synthesized hybrid compounds of tacrine and p-toluenesulfonamide are effective inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) with the preferential inhibition of BChE. They also displace propidium from the peripheral anionic site of the electric eel AChE (Electrophorus electricus). The characteristics of the efficiency and selectivity of cholinesterase inhibition by the test compounds were confirmed by the results of molecular docking.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Bachurin, S.O., Zh. Nevrol. Psikhiatr. Im. S.S. Korsakova, 2016, vol. 116, no. 8, pp. 77–87.
Rosini, M., Simoni, E., Minarini, A., and Melchiorre, C., Neurochem. Res., 2014, vol. 39, pp. 1914–1923.
Lermontova, N., Lukoyanov, N., Serkova, T., Lukoyanova, E., and Bachurin, S., Mol. Chem. Neuropathol., 1998, vol. 33, no. 1, pp. 51–61.
Nordberg, A., Ballard, C., Bullock, R., Darreh-Shori, T., and Somogyi, M., Prim. Care Companion CNS Disord., 2013, vol. 15. pii: PCC.12r01412
Milelli, A., De Simone, A., Ticchi, N., Chen, H.H., Betari, N., Andrisano, V., and Tumiatti, V., Curr. Med. Chem., 2017, vol. 24, pp. 3522–3546.
Inestrosa, N.C., Dinamarca, M.C., and Alvarez, A., FEBS J., 2008, vol. 275, no. 4, pp. 625–632.
Szymanski, P., Skibinski, R., Inglot, T., Bajda, M., Jonczyk, J., Malawska, B., and Mikiciuk-Olasik, E., Molecules, 2013, vol. 18, no. 3, pp. 2878–2894.
Supuran, C.T., Molecules, 2017, vol. 22, no. 10, pp. 1642–1646.
Bag, S., Tulsan, R., Sood, A., Cho, H., Redjeb, H., Zhou, W., LeVine, H., Török, B., and Török, M., Bioorg. Med. Chem. Lett., 2015, vol. 25, no. 3, pp. 626–630.
Hicks, L.D., Hyatt, J.L., Stoddard, S., Tsurkan, L., Edwards, C.C., Wadkins, R.M., and Potter, P.M., J. Med. Chem., 2009, vol. 52, no. 12, pp. 3742–3752.
Rosini, M., Simoni, E., Bartolini, M., Tarozzi, A., Matera, R., Milelli, A., Hrelia, P., Andrisano, V., Bolognesi, M.L., and Melchiorre, C., Eur. J. Med. Chem., 2011, vol. 46, pp. 5435–5442.
Tang, H., Zhao, L.Z., Zhao, H.T., Huang, S.L., Zhong, S.M., Qin, J.K., Chen, Z.F., Huang, Z.S., and Liang, H., Eur. J. Med. Chem., 2011, vol. 46, no. 10, pp. 4970–4979.
Makhaeva, G.F., Sokolov, V.B., Shevtsova, E.F., Kovaleva, N.V., Lushchekina, S.V., Boltneva, N.P., Rudakova, E.V., Aksinenko, A.Yu., Shevtsov, P.N., Neganova, M.E., Dubova, L.G., and Bachurin, S.O., Pure Appl. Chem., 2017, vol. 89, no. 8, pp. 1167–1184.
Kharlamova, A.D., Lushchekina, S.V., Petrov, K.A., Kots, E.D., Nachon, F., Villard-Wandhammer, M., Zueva, I.V., Krejci, E., Reznik, V.S., Zobov, V.V., Nikolsky, E.E., and Masson, P., Biochem. J., 2016, vol. 473, pp. 1225–1236.
Taylor, P. and Lappi, S., Biochemistry, 1975, vol. 14, pp. 1989–1997.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © G.F. Makhaeva, N.V. Kovaleva, S.V. Lushchekina, E.V. Rudakova, N.P. Boltneva, A.N. Proshin, B.V. Lednev, I.V. Serkov, S.O. Bachurin, 2018, published in Doklady Akademii Nauk, 2018, Vol. 483, No. 6.
Rights and permissions
About this article
Cite this article
Makhaeva, G.F., Kovaleva, N.V., Lushchekina, S.V. et al. Conjugates of Tacrine and Its Cyclic Homologues with p-Toluenesulfonamide as Novel Acetylcholinesterase and Butyrylcholinesterase Inhibitors. Dokl Biochem Biophys 483, 369–373 (2018). https://doi.org/10.1134/S1607672918060200
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1607672918060200