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

Resultado de la investigación: Article › revisión exhaustiva

Resumen

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.

Idioma original	English
Páginas (desde-hasta)	462-472
Número de páginas	11
Publicación	Chemistry of Heterocyclic Compounds
Volumen	58
N.º	8-9
DOI	https://doi.org/10.1007/s10593-022-03113-7
Estado	Published - 1 sept. 2022

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Chemistry, Multidisciplinary

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1 Terminado

Карбо- и гетероаннелирование 3-нитро-2-(трифторметил)-2Н-хроменов
Коротаев, В. Ю., Улитко, М. В., Кутяшев, И. Б., Барков, А. Ю., Зимницкий, Н. С. & Кочнев, И. А.
22/02/2020 → 27/12/2022
Proyecto: Award Project

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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

Barkovskii, Savelii V. ; Ulitko, Maria V. ; Barkov, Alexey Yu. ; Kochnev, Ivan А. ; Zimnitskiy, Nikolay S. ; Korotaev, Vladislav Yu. ; Sosnovskikh, Vyacheslav Ya. ; Stepanyuk, Roman А. ; Madzhidov, Timur I. / 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]. En: Chemistry of Heterocyclic Compounds. 2022 ; Vol. 58, N.º 8-9. pp. 462-472.

@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.}",

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, n.º 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.; Kochnev, Ivan А.; Zimnitskiy, Nikolay S.; Korotaev, Vladislav Yu.; Sosnovskikh, Vyacheslav Ya.; Stepanyuk, Roman А.; Madzhidov, Timur I.

En: Chemistry of Heterocyclic Compounds, Vol. 58, N.º 8-9, 01.09.2022, p. 462-472.

Resultado de la investigación: Article › revisión exhaustiva

TY - JOUR

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.

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.

UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=000864239000006

U2 - 10.1007/s10593-022-03113-7

DO - 10.1007/s10593-022-03113-7

M3 - Article

VL - 58

SP - 462

EP - 472

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 8-9

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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