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Annulated bicyclic isothioureas: identification of active and selective butyrylcholinesterase inhibitors

Evgeniya Vladimirovna Nurieva 1
Evgeniya Vladimirovna Nurieva
, 
Alexander Aleksandrovich Alexeev 1
Alexander Aleksandrovich Alexeev
, 
Nikolay Alekseevich Zefirov 1, 2
Nikolay Alekseevich Zefirov
, 
Elena Rudol'fovna Milaeva 1, 2
Elena Rudol'fovna Milaeva
, 
Nadezhda Vladimirovna Kovaleva 2
Nadezhda Vladimirovna Kovaleva
, 
Alexey N Proshin 2
Alexey N Proshin
, 
Galina Faivelevna Makhaeva 2
Galina Faivelevna Makhaeva
, 
Ol'ga Nikolaevna Zefirova 1, 2
Ol'ga Nikolaevna Zefirova
1 Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
2 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
10.1016/j.mencom.2023.01.024
Published 2022-12-26
Communication , Volume 33, Issue 1, 77-79
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Nurieva E. V. et al. Annulated bicyclic isothioureas: identification of active and selective butyrylcholinesterase inhibitors // Mendeleev Communications. 2022. Vol. 33. No. 1. pp. 77-79.
GOST all authors (up to 50) Copy
Nurieva E. V., Alexeev A. A., Zefirov N. A., Milaeva E. R., Kovaleva N. V., Proshin A. N., Makhaeva G. F., Zefirova O. N. Annulated bicyclic isothioureas: identification of active and selective butyrylcholinesterase inhibitors // Mendeleev Communications. 2022. Vol. 33. No. 1. pp. 77-79.
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TY - JOUR
DO - 10.1016/j.mencom.2023.01.024
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.024
TI - Annulated bicyclic isothioureas: identification of active and selective butyrylcholinesterase inhibitors
T2 - Mendeleev Communications
AU - Nurieva, Evgeniya Vladimirovna
AU - Alexeev, Alexander Aleksandrovich
AU - Zefirov, Nikolay Alekseevich
AU - Milaeva, Elena Rudol'fovna
AU - Kovaleva, Nadezhda Vladimirovna
AU - Proshin, Alexey N
AU - Makhaeva, Galina Faivelevna
AU - Zefirova, Ol'ga Nikolaevna
PY - 2022
DA - 2022/12/26
PB - Mendeleev Communications
SP - 77-79
IS - 1
VL - 33
ER -
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@article{2022_Nurieva,
author = {Evgeniya Vladimirovna Nurieva and Alexander Aleksandrovich Alexeev and Nikolay Alekseevich Zefirov and Elena Rudol'fovna Milaeva and Nadezhda Vladimirovna Kovaleva and Alexey N Proshin and Galina Faivelevna Makhaeva and Ol'ga Nikolaevna Zefirova},
title = {Annulated bicyclic isothioureas: identification of active and selective butyrylcholinesterase inhibitors},
journal = {Mendeleev Communications},
year = {2022},
volume = {33},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.024},
number = {1},
pages = {77--79},
doi = {10.1016/j.mencom.2023.01.024}
}
MLA
Cite this
MLA Copy
Nurieva, Evgeniya Vladimirovna, et al. “Annulated bicyclic isothioureas: identification of active and selective butyrylcholinesterase inhibitors.” Mendeleev Communications, vol. 33, no. 1, Dec. 2022, pp. 77-79. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.024.
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Keywords

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

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.

References

.
Synthesis, molecular docking and biological evaluation of N,N-disubstituted 2-aminothiazolines as a new class of butyrylcholinesterase and carboxylesterase inhibitors
Makhaeva G.F., Boltneva N.P., Lushchekina S.V., Serebryakova O.G., Stupina T.S., Terentiev A.A., Serkov I.V., Proshin A.N., Bachurin S.O., Richardson R.J.
Bioorganic and Medicinal Chemistry, 2016
.
Alexeev A.A., Nurieva E.V., Trofimova T.P., Chesnakova E.A., Grishin Y.K., Lyssenko K.A., Filimonova M.V., Zefirova O.N.
Mendeleev Communications, 2019
.
Selective butyrylcholinesterase inhibition elevates brain acetylcholine, augments learning and lowers Alzheimer β-amyloid peptide in rodent
Greig N.H., Utsuki T., Ingram D.K., Wang Y., Pepeu G., Scali C., Yu Q., Mamczarz J., Holloway H.W., Giordano T., Chen D., Furukawa K., Sambamurti K., Brossi A., Lahiri D.K., et. al.
Proceedings of the National Academy of Sciences of the United States of America, 2005
.
Decreased Activity of Circulating Butyrylcholinesterase in Blood Is an Independent Prognostic Marker in Pancreatic Cancer Patients
Klocker E.V., Barth D.A., Riedl J.M., Prinz F., Szkandera J., Schlick K., Kornprat P., Lackner K., Lindenmann J., Stöger H., Stotz M., Gerger A., Pichler M.
Cancers, 2020
.
New Hybrids of 4-Amino-2,3-polymethylene-quinoline and p-Tolylsulfonamide as Dual Inhibitors of Acetyl- and Butyrylcholinesterase and Potential Multifunctional Agents for Alzheimer’s Disease Treatment
Makhaeva G.F., Kovaleva N.V., Boltneva N.P., Lushchekina S.V., Astakhova T.Y., Rudakova E.V., Proshin A.N., Serkov I.V., Radchenko E.V., Palyulin V.A., Bachurin S.O., Richardson R.J.
Molecules, 2020
.
A patent review of butyrylcholinesterase inhibitors and reactivators 2010–2017
Andrisano V., Naldi M., De Simone A., Bartolini M.
Expert Opinion on Therapeutic Patents, 2018
.
“Triple” mutual prodrug based on 2-methoxyestradiol: synthesis and biotesting in vitro
Lavrushkina E.A., Shibilev V.M., Zefirov N.A., Shevtsova E.F., Shevtsov P.N., Kuznetsov S.A., Zefirova O.N.
Russian Chemical Bulletin, 2020
.
New Compounds. Isothiocyanocyclohexene and Derivative
Greenwood F., James W.
Journal of the American Chemical Society, 1951
.
Cyclic Isothiourea in Drug Design
Nurieva E.V., Alexeev A.A., Zefirova O.N.
Chemistry of Heterocyclic Compounds, 2021
.
Butyrylcholinesterase: An Important New Target in Alzheimer's Disease Therapy
Greig N.H., Lahiri D.K., Sambamurti K.
International Psychogeriatrics, 2002
.
Gu Y., Chow M.J., Kapoor A., Mei W., Jiang Y., Yan J., De Melo J., Seliman M., Yang H., Cutz J., Bonert M., Major P., Tang D.
Translational Oncology, 2018
.
Nurieva E.V., Trofimova T.P., Alexeev A.A., Proshin A.N., Chesnakova E.A., Grishin Y.K., Lyssenko K.A., Filimonova M.V., Bachurin S.O., Zefirova O.N.
Mendeleev Communications, 2018
.
Structure-activity relationship study of tryptophan-based butyrylcholinesterase inhibitors
Meden A., Knez D., Malikowska-Racia N., Brazzolotto X., Nachon F., Svete J., Sałat K., Grošelj U., Gobec S.
European Journal of Medicinal Chemistry, 2020
.
Evdokimova A.V., Alexeev A.A., Nurieva E.V., Milaeva E.R., Kuznetsov S.A., Zefirova O.N.
Mendeleev Communications, 2021
.
A New Therapeutic Target in Alzheimer's Disease Treatment: Attention to Butyrylcholinesterase
Greig N.H., Utsuki T., Yu Q., Zhu X., Holloway H.W., Perry T., Lee B., Ingram D.K., Lahiri D.K.
Current Medical Research and Opinion, 2001