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Halonal, an original benzoylated phenobarbital derivative anticonvulsant: in vivo evaluation, chemometric and molecular docking studies of enantiomers

Tamara Vladimirovna Shushpanova 1, 2
Tamara Vladimirovna Shushpanova
, 
Nikolay Aleksandrovich Bokhan 1, 3
Nikolay Aleksandrovich Bokhan
, 
Galina B Slepchenko 4
Galina B Slepchenko
, 
Evgeniya Valer'evna Markova 5
Evgeniya Valer'evna Markova
, 
Olga V Shushpanova 6
Olga V Shushpanova
, 
Irina N Smirnova 2
Irina N Smirnova
, 
Alexei Aleksandrovich Zaitsev 2
Alexei Aleksandrovich Zaitsev
, 
Natalia Eduardovna Kolomiets 3, 7
Natalia Eduardovna Kolomiets
,  , 
Viktor Dmitrievich Filimonov 4
Viktor Dmitrievich Filimonov
1 Mental Health Research Institute, Tomsk National Research Medical Center, Russian Academy of Sciences, Tomsk, Russian Federation
2 Tomsk Research Institute of Balneology and Physiotherapy, Federal Scientific and Clinical Center for Medical Rehabilitation and Balneology, Tomsk, Russian Federation
3 Siberian State Medical University, Tomsk, Russian Federation
4 National Research Tomsk Polytechnic University, Tomsk, Russian Federation
5 Research Institute of Fundamental and Clinical Immunology, Novosibirsk, Russian Federation
6 Scientific Center for Mental Health, Moscow, Russian Federation
7 Kemerovo State Medical University, Kemerovo, Russia
10.1016/j.mencom.2024.10.027
Published 2024-10-22
Communication , Volume 34, Issue 6, 854-858
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Shushpanova T. V. et al. Halonal, an original benzoylated phenobarbital derivative anticonvulsant: in vivo evaluation, chemometric and molecular docking studies of enantiomers // Mendeleev Communications. 2024. Vol. 34. No. 6. pp. 854-858.
GOST all authors (up to 50) Copy
Shushpanova T. V., Bokhan N. A., Slepchenko G. B., Markova E. V., Shushpanova O. V., Smirnova I. N., Zaitsev A. A., Kolomiets N. E., Kuksenok V. Y., Filimonov V. D. Halonal, an original benzoylated phenobarbital derivative anticonvulsant: in vivo evaluation, chemometric and molecular docking studies of enantiomers // Mendeleev Communications. 2024. Vol. 34. No. 6. pp. 854-858.
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TY - JOUR
DO - 10.1016/j.mencom.2024.10.027
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.10.027
TI - Halonal, an original benzoylated phenobarbital derivative anticonvulsant: in vivo evaluation, chemometric and molecular docking studies of enantiomers
T2 - Mendeleev Communications
AU - Shushpanova, Tamara Vladimirovna
AU - Bokhan, Nikolay Aleksandrovich
AU - Slepchenko, Galina B
AU - Markova, Evgeniya Valer'evna
AU - Shushpanova, Olga V
AU - Smirnova, Irina N
AU - Zaitsev, Alexei Aleksandrovich
AU - Kolomiets, Natalia Eduardovna
AU - Kuksenok, Vera Yur'evna
AU - Filimonov, Viktor Dmitrievich
PY - 2024
DA - 2024/10/22
PB - Mendeleev Communications
SP - 854-858
IS - 6
VL - 34
ER -
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@article{2024_Shushpanova,
author = {Tamara Vladimirovna Shushpanova and Nikolay Aleksandrovich Bokhan and Galina B Slepchenko and Evgeniya Valer'evna Markova and Olga V Shushpanova and Irina N Smirnova and Alexei Aleksandrovich Zaitsev and Natalia Eduardovna Kolomiets and Vera Yur'evna Kuksenok and Viktor Dmitrievich Filimonov},
title = {Halonal, an original benzoylated phenobarbital derivative anticonvulsant: in vivo evaluation, chemometric and molecular docking studies of enantiomers},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.10.027},
number = {6},
pages = {854--858},
doi = {10.1016/j.mencom.2024.10.027}
}
MLA
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Shushpanova, Tamara Vladimirovna, et al. “Halonal, an original benzoylated phenobarbital derivative anticonvulsant: in vivo evaluation, chemometric and molecular docking studies of enantiomers.” Mendeleev Communications, vol. 34, no. 6, Oct. 2024, pp. 854-858. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.10.027.

Keywords

2-fluorobenzoyl substituent.
anticonvulsant
barbiturates
enantiomer
GABAA receptor
molecular docking
γ-aminobutyric acid

Abstract

An original phenobarbital anticonvulsant Halonal, 5-ethyl-1-(2-fluorobenzoyl)-5-phenylpyrimidine-2,4,6(1H,3H,5H)-trione, stimulated the cellular immune and the humoral response in long-term alcoholized male (CBAxC57Bl/6) F1 mice to the level of healthy animals. Voltammetry was found to be suitable for determination of Halonal R/S-enantiomeric ratio, which was exemplified on the authentic sample with the R/S-composition of 40:60. Molecular docking (Schrodinger program, Glide) showed that Halonal behaved as a benzonal derivative interacting with GABAAR via the BARB binding site, with S-Halonal having higher similarity score than its R-enantiomer because of a different orientation of the 2-fluorobenzoyl substituent.

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