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Positive and negative AMPA receptor modulators based on tricyclic bispidine derivative: Minor structural change inverts the type of activity

Mstislav Igorevich Lavrov 1
Mstislav Igorevich Lavrov
,  , 
Elena Andreevna Golubeva 1
Elena Andreevna Golubeva
, 
Eugene V Radchenko 1
Eugene V Radchenko
, 
Vladimir Lollievich Zamoyski 2
Vladimir Lollievich Zamoyski
, 
Vladimir Viktorovich Grigoriev 1, 2
Vladimir Viktorovich Grigoriev
, 
Vladimir Alexandrovich Palyulin 1
Vladimir Alexandrovich Palyulin
10.1016/j.mencom.2022.05.023
Published 2022-04-29
Communication , Volume 32, Issue 3, 360-363
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Lavrov M. I. et al. Positive and negative AMPA receptor modulators based on tricyclic bispidine derivative: Minor structural change inverts the type of activity // Mendeleev Communications. 2022. Vol. 32. No. 3. pp. 360-363.
GOST all authors (up to 50) Copy
Lavrov M. I., Veremeeva P. N., Golubeva E. A., Radchenko E. V., Zamoyski V. L., Grigoriev V. V., Palyulin V. A. Positive and negative AMPA receptor modulators based on tricyclic bispidine derivative: Minor structural change inverts the type of activity // Mendeleev Communications. 2022. Vol. 32. No. 3. pp. 360-363.
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TY - JOUR
DO - 10.1016/j.mencom.2022.05.023
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.023
TI - Positive and negative AMPA receptor modulators based on tricyclic bispidine derivative: Minor structural change inverts the type of activity
T2 - Mendeleev Communications
AU - Lavrov, Mstislav Igorevich
AU - Veremeeva, Polina Nikolaevna
AU - Golubeva, Elena Andreevna
AU - Radchenko, Eugene V
AU - Zamoyski, Vladimir Lollievich
AU - Grigoriev, Vladimir Viktorovich
AU - Palyulin, Vladimir Alexandrovich
PY - 2022
DA - 2022/04/29
PB - Mendeleev Communications
SP - 360-363
IS - 3
VL - 32
ER -
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@article{2022_Lavrov,
author = {Mstislav Igorevich Lavrov and Polina Nikolaevna Veremeeva and Elena Andreevna Golubeva and Eugene V Radchenko and Vladimir Lollievich Zamoyski and Vladimir Viktorovich Grigoriev and Vladimir Alexandrovich Palyulin},
title = {Positive and negative AMPA receptor modulators based on tricyclic bispidine derivative: Minor structural change inverts the type of activity},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.023},
number = {3},
pages = {360--363},
doi = {10.1016/j.mencom.2022.05.023}
}
MLA
Cite this
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Lavrov, Mstislav Igorevich, et al. “Positive and negative AMPA receptor modulators based on tricyclic bispidine derivative: Minor structural change inverts the type of activity.” Mendeleev Communications, vol. 32, no. 3, Apr. 2022, pp. 360-363. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.023.

Keywords

3,7-diazabicyclo[3.3.1]nonane
allosteric modulators
AMPA receptors
bispidines
heterocyclization

Abstract

Two new potent AMPA receptor allosteric modulators, 6-(1,3-benzodioxol-5-yl)-1,11-dimethyl-3,6,9-triazatri-cyclo[7.3.1.13,11]tetradecane-4,8,12-trione and -4,8-dione were synthesized from 1,3-benzodioxol-5-amine and the corresponding 3,7-dichloroacetyl-3,7-diazabicyclo[3.3.1]-nonanes. In a wide concentration range (10−12–10−7 m), the 12-oxo derivative acts as a positive modulator causing the potentiation of the kainate-induced AMPA receptor currents with maximum potentiation at 1 nm (62%) while its analogue without a ketone group has significant (up to 40%) negative modulator effect. Their tentative mechanisms of action were analyzed by means of molecular modelling

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