Current Organic Synthesis, volume 17, issue 1, pages 29-39
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 Selectivity
Publication type: Journal Article
Publication date: 2020-02-24
Journal:
Current Organic Synthesis
Quartile SCImago
Q3
Quartile WOS
Q3
Impact factor: 1.8
ISSN: 15701794
Organic Chemistry
Biochemistry
Abstract
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.
Material and Method:
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.
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Chemical Data Collections
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RSC Advances
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RSC Advances
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Multidisciplinary Digital Publishing Institute (MDPI)
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Elsevier
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Elsevier
1 publication, 25%
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Royal Society of Chemistry (RSC)
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Royal Society of Chemistry (RSC)
1 publication, 25%
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Buravchenko G. I. et al. 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 Selectivity // Current Organic Synthesis. 2020. Vol. 17. No. 1. pp. 29-39.
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Buravchenko G. I., Scherbakov A. M., Korlyukov A., Dorovatovskii P., Shchekotikhin A. 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 Selectivity // Current Organic Synthesis. 2020. Vol. 17. No. 1. pp. 29-39.
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TY - JOUR
DO - 10.2174/1570179416666191210100754
UR - https://doi.org/10.2174%2F1570179416666191210100754
TI - 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 Selectivity
T2 - Current Organic Synthesis
AU - Buravchenko, Galina I.
AU - Scherbakov, Alexander M.
AU - Korlyukov, Alexander
AU - Dorovatovskii, Pavel
AU - Shchekotikhin, Andrey
PY - 2020
DA - 2020/02/24 00:00:00
PB - Bentham Science
SP - 29-39
IS - 1
VL - 17
SN - 1570-1794
ER -
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@article{2020_Buravchenko,
author = {Galina I. Buravchenko and Alexander M. Scherbakov and Alexander Korlyukov and Pavel Dorovatovskii and Andrey Shchekotikhin},
title = {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 Selectivity},
journal = {Current Organic Synthesis},
year = {2020},
volume = {17},
publisher = {Bentham Science},
month = {feb},
url = {https://doi.org/10.2174%2F1570179416666191210100754},
number = {1},
pages = {29--39},
doi = {10.2174/1570179416666191210100754}
}
Cite this
MLA
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Buravchenko, Galina I., et al. “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 Selectivity.” Current Organic Synthesis, vol. 17, no. 1, Feb. 2020, pp. 29-39. https://doi.org/10.2174%2F1570179416666191210100754.