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Revision of the Regioselectivity of the Beirut Reaction of Monosubstituted Benzofuroxans With Benzoylacetonitrile. 6-Substituted quinoxaline-2-carbonitrile 1,4- Dioxides: Structural Characterization and Estimation of Anticancer Activity and Hypoxia Selectстатья
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Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 16 сентября 2020 г.
- Авторы: Buravchenko GI, Scherbakov AM, Korlukov AА, Dorovatovskii PV, Shchekotikhin AE
- Журнал: Current Organic Synthesis
- Том: 17
- Номер: 1
- Год издания: 2020
- Издательство: Bentham Science Publishers
- Местоположение издательства: Netherlands
- Первая страница: 29
- Последняя страница: 39
- DOI: 10.2174/1570179416666191210100754
- Аннотация: Background: Quinoxaline 1,4-dioxides have a broad range of biological activity that causes a growing interest in their derivatives for drug discovery. Recent studies demonstrated that quinoxaline 1,4- dioxides have a promising anticancer activity and good hypoxia-selectivity.Objective: The preparation, isolation, structure characterization, and screening for anticancer activity of the first representatives of 6-substituted quinoxaline-2-carbonitrile 1,4-dioxides have been described.Materials and methods: A series of 7- and 6-halogeno-3-phenylquinoxaline-2-carbonitrile 1,4-dioxides was synthesized by the Beirut reaction. The cytotoxicity was assessed by MTT test (72 h incubation) in normoxia (21% O2) and hypoxia (1% O2) conditions.Results: We found that during the Beirut reaction between a benzofuroxan bearing an electron withdrawing group and benzoylacetonitrile in the presence of triethylamine, in addition to well-known 7-substituted quinoxaline-2-carbonitrile 1,4-dioxides 7-11a, the 6-isomers 7-11b are formed. Moreover, the yield of the 6- isomers increased with the increase in the electron-withdrawing character of the substituent. For benzofuroxans with CO2Me and CF3 groups, 6-substituted quinoxaline-2-carbonitrile 1,4-dioxides 10-11b were the major products. Despite similarities in physicochemical and spectroscopic properties, the obtained isomers exhibit considerable differences in their anticancer activity and hypoxia selectivity.Conclusion: Substituents and their electronic effects play a key role in the formation of 7- and 6-substituted quinoxaline-2-carbonitrile 1,4-dioxides in the Beirut reaction and in the cytotoxicity properties of the obtained isomers.
- Добавил в систему: Щекотихин Андрей Егорович