Home / Publications / New 1,11-dimethyl-3,6,9-triazatricyclo[7.3.1.13,11]tetradecane-4,8,12-trione derivative as an allosteric modulator of the glutamatergic system

New 1,11-dimethyl-3,6,9-triazatricyclo[7.3.1.13,11]tetradecane-4,8,12-trione derivative as an allosteric modulator of the glutamatergic system

Elena Andreevna Golubeva 1
Elena Andreevna Golubeva
Mstislav Igorevich Lavrov 1
Mstislav Igorevich Lavrov
Evgenia Mikhailovna Bovina 1
Evgenia Mikhailovna Bovina
Eugene V Radchenko 1
Eugene V Radchenko
Andrey Fedorovich Asachenko 2
Andrey Fedorovich Asachenko
Vladimir Lollievich Zamoyski 3
Vladimir Lollievich Zamoyski
Vladimir Viktorovich Grigoriev 1, 3
Vladimir Viktorovich Grigoriev
Vladimir Alexandrovich Palyulin 1
Vladimir Alexandrovich Palyulin
1 Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
2 A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Moscow, Russian Federation
3 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
Published 2022-12-26
CommunicationVolume 33, Issue 1, 70-72
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Golubeva E. A. et al. New 1,11-dimethyl-3,6,9-triazatricyclo[7.3.1.13,11]tetradecane-4,8,12-trione derivative as an allosteric modulator of the glutamatergic system // Mendeleev Communications. 2022. Vol. 33. No. 1. pp. 70-72.
GOST all authors (up to 50) Copy
Golubeva E. A., Lavrov M. I., Veremeeva P. N., Bovina E. M., Radchenko E. V., Topchiy M. A., Asachenko A. F., Zamoyski V. L., Grigoriev V. V., Palyulin V. A. New 1,11-dimethyl-3,6,9-triazatricyclo[7.3.1.13,11]tetradecane-4,8,12-trione derivative as an allosteric modulator of the glutamatergic system // Mendeleev Communications. 2022. Vol. 33. No. 1. pp. 70-72.
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TY - JOUR
DO - 10.1016/j.mencom.2023.01.022
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.022
TI - New 1,11-dimethyl-3,6,9-triazatricyclo[7.3.1.13,11]tetradecane-4,8,12-trione derivative as an allosteric modulator of the glutamatergic system
T2 - Mendeleev Communications
AU - Golubeva, Elena Andreevna
AU - Lavrov, Mstislav Igorevich
AU - Veremeeva, Polina Nikolaevna
AU - Bovina, Evgenia Mikhailovna
AU - Radchenko, Eugene V
AU - Topchiy, Maxim Anatol'evich
AU - Asachenko, Andrey Fedorovich
AU - Zamoyski, Vladimir Lollievich
AU - Grigoriev, Vladimir Viktorovich
AU - Palyulin, Vladimir Alexandrovich
PY - 2022
DA - 2022/12/26
PB - Mendeleev Communications
SP - 70-72
IS - 1
VL - 33
ER -
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@article{2022_Golubeva,
author = {Elena Andreevna Golubeva and Mstislav Igorevich Lavrov and Polina Nikolaevna Veremeeva and Evgenia Mikhailovna Bovina and Eugene V Radchenko and Maxim Anatol'evich Topchiy and Andrey Fedorovich Asachenko and Vladimir Lollievich Zamoyski and Vladimir Viktorovich Grigoriev and Vladimir Alexandrovich Palyulin},
title = {New 1,11-dimethyl-3,6,9-triazatricyclo[7.3.1.13,11]tetradecane-4,8,12-trione derivative as an allosteric modulator of the glutamatergic system},
journal = {Mendeleev Communications},
year = {2022},
volume = {33},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.022},
number = {1},
pages = {70--72},
doi = {10.1016/j.mencom.2023.01.022}
}
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Golubeva, Elena Andreevna, et al. “New 1,11-dimethyl-3,6,9-triazatricyclo[7.3.1.13,11]tetradecane-4,8,12-trione derivative as an allosteric modulator of the glutamatergic system.” Mendeleev Communications, vol. 33, no. 1, Dec. 2022, pp. 70-72. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.022.
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Keywords

3
7-diazabicyclo[3.3.1]nonanes
allosteric modulators
AMPA receptor
cross-coupling
indane derivatives
nitriles
PAMs
patch clamp.
piperonylic acid

Abstract

An optimized synthesis of N-{5-[(1,11-dimethyl-4,8,12-trioxo-3,6,9-triazatricyclo[7.3.1.13,11]tetradec-6-yl)methyl]-indan-2-yl}-1,3-benzodioxole-5-carboxamide has been carried out from indan-2-one oxime in seven steps. In vitro studies using electrophysiological patch clamp technique have revealed a positive modulation effect of this compound on kainate induced currents in Purkinje neurons in a wide range of concentrations from 10-12 to 10-8 m.

References

.
GROMACS: High performance molecular simulations through multi-level parallelism from laptops to supercomputers
Abraham M.J., Murtola T., Schulz R., Páll S., Smith J.C., Hess B., Lindahl E.
SoftwareX, 2015
.
CHARMM general force field: A force field for drug-like molecules compatible with the CHARMM all-atom additive biological force fields
Vanommeslaeghe K., Hatcher E., Acharya C., Kundu S., Zhong S., Shim J., Darian E., Guvench O., Lopes P., Vorobyov I., Mackerell A.D.
Journal of Computational Chemistry, 2009
.
MM-GBSA and MM-PBSA performance in activity evaluation of AMPA receptor positive allosteric modulators
Karlov D.S., Lavrov M.I., Palyulin V.A., Zefirov N.S.
Journal of Biomolecular Structure and Dynamics, 2017
.
Lavrov M.I., Veremeeva P.N., Karlov D.S., Zamoyski V.L., Grigoriev V.V., Palyulin V.A.
Mendeleev Communications, 2019
.
MMPBSA.py: An Efficient Program for End-State Free Energy Calculations
Miller B.R., McGee T.D., Swails J.M., Homeyer N., Gohlke H., Roitberg A.E.
Journal of Chemical Theory and Computation, 2012
.
Enhancing Action of Positive Allosteric Modulators through the Design of Dimeric Compounds
Drapier T., Geubelle P., Bouckaert C., Nielsen L., Laulumaa S., Goffin E., Dilly S., Francotte P., Hanson J., Pochet L., Kastrup J.S., Pirotte B.
Journal of Medicinal Chemistry, 2018
.
gmx_MMPBSA: A New Tool to Perform End-State Free Energy Calculations with GROMACS
Valdés-Tresanco M.S., Valdés-Tresanco M.E., Valiente P.A., Moreno E.
Journal of Chemical Theory and Computation, 2021
.
S 47445 Produces Antidepressant- and Anxiolytic-Like Effects through Neurogenesis Dependent and Independent Mechanisms
Mendez-David I., Guilloux J., Papp M., Tritschler L., Mocaer E., Gardier A.M., Bretin S., David D.J.
Frontiers in Pharmacology, 2017
.
Pharmacophore analysis of positive allosteric modulators of AMPA receptors
Karlov D.S., Lavrov M.I., Palyulin V.A., Zefirov N.S.
Russian Chemical Bulletin, 2016
.
PHYSIOLOGICALLY ACTIVE INDANAMINES1
LEVIN N., GRAHAM B.E., KOLLOFF H.G.
Journal of Organic Chemistry, 1944
.
Comparison of biological effects of N-alkylated congeners of .beta.-phenethylamine derived from 2-aminotetralin, 2-aminoindan, and 6-aminobenzocycloheptene
Cannon J.G., Perez J.A., Pease J.P., Long J.P., Flynn J.R., Rusterholz D.B., Dryer S.E.
Journal of Medicinal Chemistry, 1980
.
Antidepressant-Like Effects of CX717, a Positive Allosteric Modulator of AMPA Receptors
Gordillo-Salas M., Pascual-Antón R., Ren J., Greer J., Adell A.
Molecular Neurobiology, 2020
.
Temnyakova N.S., Vasilenko D.A., Lavrov M.I., Karlov D.S., Grishin Y.K., Zamoyski V.L., Grigoriev V.V., Averina E.B., Palyulin V.A.
Mendeleev Communications, 2021
.
Chronic Ampakine Treatments Stimulate Dendritic Growth and Promote Learning in Middle-Aged Rats
Lauterborn J.C., Palmer L.C., Jia Y., Pham D.T., Hou B., Wang W., Trieu B.H., Cox C.D., Kantorovich S., Gall C.M., Lynch G.
Journal of Neuroscience, 2016
.
Radchenko E.V., Karlov D.S., Lavrov M.I., Palyulin V.A.
Mendeleev Communications, 2017
.
Lavrov M.I., Karlov D.S., Palyulin V.A., Grigoriev V.V., Zamoyski V.L., Brkich G.E., Pyatigorskaya N.V., Zapolskiy M.E.
Mendeleev Communications, 2018
.
AMPA receptor positive allosteric modulators: a patent review
Pirotte B., Francotte P., Goffin E., de Tullio P.
Expert Opinion on Therapeutic Patents, 2013
.
Acute ampakine treatment ameliorates age-related deficits in long-term potentiation
Radin D.P., Zhong S., Purcell R., Lippa A.
Biomedicine and Pharmacotherapy, 2016
.
Upregulation of neurotrophins by S 47445, a novel positive allosteric modulator of AMPA receptors in aged rats
Calabrese F., Savino E., Mocaer E., Bretin S., Racagni G., Riva M.A.
Pharmacological Research, 2017
.
Effects of chronic systemic low-impact ampakine treatment on neurotrophin expression in rat brain
Radin D.P., Johnson S., Purcell R., Lippa A.S.
Biomedicine and Pharmacotherapy, 2018
.
Lavrov M.I., Stroganov O.V., Zamoyski V.L., Grigoriev V.V., Zapolskiy M.E., Sysolyatin S.V., Malykhin V.V., Surmachev V.N., Palyulin V.A.
Mendeleev Communications, 2020
.
Lavrov M.I., Veremeeva P.N., Golubeva E.A., Radchenko E.V., Zamoyski V.L., Grigoriev V.V., Palyulin V.A.
Mendeleev Communications, 2022