The synthesis and cytotoxic activity of N-unsubstituted 3-aryl-4-(trifluoromethyl)-4H-spiro[chromeno[3,4-c]pyrrolidine-1,11'-indeno[1,2-b]quinoxalines]

Savelii V. Barkovskii; Maria V. Ulitko; Alexey Yu. Barkov; Ivan А. Kochnev; Nikolay S. Zimnitskiy; Vladislav Yu. Korotaev; Vyacheslav Ya. Sosnovskikh; Roman А. Stepanyuk; Timur I. Madzhidov

doi:10.1007/s10593-022-03113-7

The synthesis and cytotoxic activity of N-unsubstituted 3-aryl-4-(trifluoromethyl)-4H-spiro[chromeno[3,4-c]pyrrolidine-1,11'-indeno[1,2-b]quinoxalines]

Savelii V. Barkovskii, Maria V. Ulitko, Alexey Yu. Barkov, Ivan А. Kochnev, Nikolay S. Zimnitskiy, Vladislav Yu. Korotaev, Vyacheslav Ya. Sosnovskikh, Roman А. Stepanyuk, Timur I. Madzhidov

Research output: Contribution to journal › Article › peer-review

Abstract

A method for a regio- and stereoselective synthesis of N-unsubstituted 3-aryl-4-(trifluoromethyl)-4H-spiro[chromeno[3,4-c]pyrrolidine-1,11'-indeno[1,2-b]quinoxalines] in 52-85% yields based on the three-component reaction of 3-nitro-2-trifluoromethyl-2H-chromenes with azomethine ylides generated in situ from benzylamines and indeno[1,2-b]quinoxalin-11-one by heating under reflux in CH2Cl2 for 2 h in the presence of 0.1 equiv of pyrrolidine was developed. The resulting compounds exhibited moderate cytotoxic activity against HeLa human cervical carcinoma cells in the concentration range of 10(-5)-10(-4) M.

Original language	English
Pages (from-to)	462-472
Number of pages	11
Journal	Chemistry of Heterocyclic Compounds
Volume	58
Issue number	8-9
DOIs	https://doi.org/10.1007/s10593-022-03113-7
Publication status	Published - 1 Sep 2022

ASJC Scopus subject areas

Organic Chemistry

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Chemistry, Multidisciplinary

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Barkovskii, S. V., Ulitko, M. V., Barkov, A. Y., Kochnev, I. А., Zimnitskiy, N. S., Korotaev, V. Y., Sosnovskikh, V. Y., Stepanyuk, R. А., & Madzhidov, T. I. (2022). The synthesis and cytotoxic activity of N-unsubstituted 3-aryl-4-(trifluoromethyl)-4H-spiro[chromeno[3,4-c]pyrrolidine-1,11'-indeno[1,2-b]quinoxalines]. Chemistry of Heterocyclic Compounds, 58(8-9), 462-472. https://doi.org/10.1007/s10593-022-03113-7

@article{c75e3fb8652b4a7bace476ad8e027fa1,

title = "The synthesis and cytotoxic activity of N-unsubstituted 3-aryl-4-(trifluoromethyl)-4H-spiro[chromeno[3,4-c]pyrrolidine-1,11'-indeno[1,2-b]quinoxalines]",

abstract = "A method for a regio- and stereoselective synthesis of N-unsubstituted 3-aryl-4-(trifluoromethyl)-4H-spiro[chromeno[3,4-c]pyrrolidine-1,11'-indeno[1,2-b]quinoxalines] in 52-85% yields based on the three-component reaction of 3-nitro-2-trifluoromethyl-2H-chromenes with azomethine ylides generated in situ from benzylamines and indeno[1,2-b]quinoxalin-11-one by heating under reflux in CH2Cl2 for 2 h in the presence of 0.1 equiv of pyrrolidine was developed. The resulting compounds exhibited moderate cytotoxic activity against HeLa human cervical carcinoma cells in the concentration range of 10(-5)-10(-4) M.",

author = "Barkovskii, {Savelii V.} and Ulitko, {Maria V.} and Barkov, {Alexey Yu.} and Kochnev, {Ivan А.} and Zimnitskiy, {Nikolay S.} and Korotaev, {Vladislav Yu.} and Sosnovskikh, {Vyacheslav Ya.} and Stepanyuk, {Roman А.} and Madzhidov, {Timur I.}",

note = "This work was supported financially by the Russian Foundation for Basic Research (project no. 20-03-00716) within the framework of the State assignment of the Ministry of Science and Higher Education of the Russian Federation (project FEUZ-2020-0052). The authors are grateful to the staff of the Center for Collective Use “Spectroscopy and Analysis of Organic Compounds” of the Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences for help in conducting physicochemical studies.",

year = "2022",

month = sep,

day = "1",

doi = "10.1007/s10593-022-03113-7",

language = "English",

volume = "58",

pages = "462--472",

journal = "Chemistry of Heterocyclic Compounds",

issn = "0009-3122",

publisher = "Springer Verlag",

number = "8-9",

}

Barkovskii, SV, Ulitko, MV , Barkov, AY , Kochnev, IА , Zimnitskiy, NS , Korotaev, VY , Sosnovskikh, VY, Stepanyuk, RА & Madzhidov, TI 2022, 'The synthesis and cytotoxic activity of N-unsubstituted 3-aryl-4-(trifluoromethyl)-4H-spiro[chromeno[3,4-c]pyrrolidine-1,11'-indeno[1,2-b]quinoxalines]', Chemistry of Heterocyclic Compounds, vol. 58, no. 8-9, pp. 462-472. https://doi.org/10.1007/s10593-022-03113-7

The synthesis and cytotoxic activity of N-unsubstituted 3-aryl-4-(trifluoromethyl)-4H-spiro[chromeno[3,4-c]pyrrolidine-1,11'-indeno[1,2-b]quinoxalines]. / Barkovskii, Savelii V.; Ulitko, Maria V.; Barkov, Alexey Yu. et al.

In: Chemistry of Heterocyclic Compounds, Vol. 58, No. 8-9, 01.09.2022, p. 462-472.

Research output: Contribution to journal › Article › peer-review

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T1 - The synthesis and cytotoxic activity of N-unsubstituted 3-aryl-4-(trifluoromethyl)-4H-spiro[chromeno[3,4-c]pyrrolidine-1,11'-indeno[1,2-b]quinoxalines]

AU - Barkovskii, Savelii V.

AU - Ulitko, Maria V.

AU - Barkov, Alexey Yu.

AU - Kochnev, Ivan А.

AU - Zimnitskiy, Nikolay S.

AU - Korotaev, Vladislav Yu.

AU - Sosnovskikh, Vyacheslav Ya.

AU - Stepanyuk, Roman А.

AU - Madzhidov, Timur I.

N1 - This work was supported financially by the Russian Foundation for Basic Research (project no. 20-03-00716) within the framework of the State assignment of the Ministry of Science and Higher Education of the Russian Federation (project FEUZ-2020-0052). The authors are grateful to the staff of the Center for Collective Use “Spectroscopy and Analysis of Organic Compounds” of the Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences for help in conducting physicochemical studies.

PY - 2022/9/1

Y1 - 2022/9/1

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AB - A method for a regio- and stereoselective synthesis of N-unsubstituted 3-aryl-4-(trifluoromethyl)-4H-spiro[chromeno[3,4-c]pyrrolidine-1,11'-indeno[1,2-b]quinoxalines] in 52-85% yields based on the three-component reaction of 3-nitro-2-trifluoromethyl-2H-chromenes with azomethine ylides generated in situ from benzylamines and indeno[1,2-b]quinoxalin-11-one by heating under reflux in CH2Cl2 for 2 h in the presence of 0.1 equiv of pyrrolidine was developed. The resulting compounds exhibited moderate cytotoxic activity against HeLa human cervical carcinoma cells in the concentration range of 10(-5)-10(-4) M.

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ER -

The synthesis and cytotoxic activity of N-unsubstituted 3-aryl-4-(trifluoromethyl)-4H-spiro[chromeno[3,4-c]pyrrolidine-1,11'-indeno[1,2-b]quinoxalines]

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Карбо- и гетероаннелирование 3-нитро-2-(трифторметил)-2Н-хроменов

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The synthesis and cytotoxic activity of N-unsubstituted 3-aryl-4-(trifluoromethyl)-4H-spiro[chromeno[3,4-c]pyrrolidine-1,11'-indeno[1,2-b]quinoxalines]

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Карбо- и гетероаннелирование 3-нитро-2-(трифторметил)-2Н-хроменов

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