E/Z Isomerism of the Potential Antiepileptic Drug GIZH-298 | Sciact

E/Z Isomerism of the Potential Antiepileptic Drug GIZH-298 Научная публикация

Журнал

Molecules
ISSN: 1420-3049

Вых. Данные

Год: 2026, Том: 31, Номер: 11, Номер статьи : 1872, Страниц : DOI: 10.3390/molecules31111872

Авторы

Mokrov Grigory V. ¹ , Litvinova Svetlana A. ² , Biryukova Valentina E. ¹ , Voronina Tatiana A. ² , Shorunov Sergey V. ¹ , Rebeko Alexey G. ¹ , Vorobyova Tatiana Yu. ¹ , Grushevskaya Liubov N. ³ , Sergeeva Maria S. ³ , Kuznetsov Dmitry N. ³ , Kravtsova Oxana Yu. ⁴ , Nikitina Ekaterina A. ² , Gladysheva Natalia A. ² , Zhanataev Aliy K. ⁵ , Durnev Andrey D. ⁵ , Losev Timofey V. ⁶ , Malashkeevich Ksenia M. ⁶ , Medvedev Michael G. ⁶ , Islamov Marat M. ⁷ , Lyssenko Konstantin A. ⁷ , Dorofeev Vladimir L. ^8,3

Организации

1	Department of Medicinal Chemistry, Federal Research Center for Innovator and Emerging Biomedical and Pharmaceutical Technologies, Baltiyskaya 8, 125315 Moscow, Russia
2	Department of Neuropsychopharmacology, Federal Research Center for Innovator and Emerging Biomedical and Pharmaceutical Technologies, Baltiyskaya 8, 125315 Moscow, Russia
3	Laboratory of Standardization and Quality Control, Federal Research Center for Innovator and Emerging Biomedical and Pharmaceutical Technologies, Baltiyskaya 8, 125315 Moscow, Russia
4	Pharmacokinetics Laboratory, Federal Research Center for Innovator and Emerging Biomedical and Pharmaceutical Technologies, Baltiyskaya 8, 125315 Moscow, Russia
5	Department of Toxicology, Federal Research Center for Innovator and Emerging Biomedical and Pharmaceutical Technologies, Baltiyskaya 8, 125315 Moscow, Russia
6	Group of Theoretical Chemistry, Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt 47, 119991 Moscow, Russia
7	Faculty of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1/3, 119991 Moscow, Russia
8	Federal Research Center for Innovator and Emerging Biomedical and Pharmaceutical Technologies, Baltiyskaya 8, 125315 Moscow, Russia

The synthesis, purification, and comprehensive characterization of the E- and Z-isomers of the prospective anticonvulsant compound GIZH-298 were carried out. It was demonstrated that both isomers could be obtained in a pure form by isolating the corresponding oximes at the initial stage of synthesis. The E- and Z-isomers exhibit pronounced differences in their physicochemical characteristics, spectral features, and pharmacological profiles. Z-GIZH-298 was found to be photosensitive, undergoing Z-E isomerization upon irradiation, as confirmed by both theoretical analysis and experimental observations. Additionally, partial conversion to the E-form occurs during prolonged reflux of Z-GIZH-298 in polar solvents, whereas the compound remains stable in aqueous and acidic media at ambient temperature. In the maximal electroshock assay, both isomers demonstrated anticonvulsant activity, with Z-GIZH-298 showing substantially higher efficacy than its E-counterpart. These findings highlight the need to account for potential E-isomer formation when considering further development of Z-GIZH-298 as a promising anticonvulsant agent.

Mokrov G.V. , Litvinova S.A. , Biryukova V.E. , Voronina T.A. , Shorunov S.V. , Rebeko A.G. , Vorobyova T.Y. , Grushevskaya L.N. , Sergeeva M.S. , Kuznetsov D.N. , Kravtsova O.Y. , Nikitina E.A. , Gladysheva N.A. , Zhanataev A.K. , Durnev A.D. , Losev T.V. , Malashkeevich K.M. , Medvedev M.G. , Islamov M.M. , Lyssenko K.A. , Dorofeev V.L.
E/Z Isomerism of the Potential Antiepileptic Drug GIZH-298
Molecules. 2026. V.31. N11. 1872 . DOI: 10.3390/molecules31111872 OpenAlex

Поступила в редакцию:	20 апр. 2026 г.
Опубликована online:	29 мая 2026 г.

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