E. V. Nurieva, A. A. Alexeev, N. A. Zefirov, E. R. Milaeva, N. V. Kovaleva, A. N. Proshin, G. F. Makhaeva, O. N. Zefirova, “Annulated bicyclic isothioureas: identification of active and selective butyrylcholinesterase inhibitors”, Mendeleev Commun., 2023, Volume 33, Issue 1,Pages <nobr>77

This article is cited in 5 papers

Communications

Annulated bicyclic isothioureas: identification of active and selective butyrylcholinesterase inhibitors

E. V. Nurieva^a, A. A. Alexeev^a, N. A. Zefirov^ab, E. R. Milaeva^ab, N. V. Kovaleva^b, A. N. Proshin^b, G. F. Makhaeva^b, O. N. Zefirova^ab

^a Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
^b Institute of Physiologically Active Compounds, Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, Chernogolovka, Moscow Region, Russian Federation

Abstract: Structural optimization of butyrylcholinesterase inhibitors, 5-bromomethyl- and 5-iodomethyl-N,N-disubstituted 2-aminothiazolines, led to a series of their annulated bicyclic analogues, obtained by intramolecular cyclization of cycloalkenylthioureas. The most active compound in this series, cyclohepta[d]thiazol-2-amine, is a mixed-type butyryl-cholinesterase inhibitor with IC₅₀ = 130 nm, highly selective compared to acetylcholinesterase and non-toxic at 100 μm concentrations.

Keywords: bicyclic isothioureas, cycloalka[d]thiazole-2-amine, thioureas, 2-aminothiazolines, heterocyclization, butyrylcholinesterase inhibitors, Alzheimer’s disease, cytotoxicity.

Language: English

DOI: 10.1016/j.mencom.2023.01.024

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