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Effective Synthesis of 3,4-Diaryl-isoxazole-5-carboxamides and their Antiproliferative Properties. / Maksimenko, Anna S.; Kislyi, Victor P.; Chernysheva, Natalia B. и др.

в: European Journal of Organic Chemistry, Том 2019, № 26, 14.07.2019, стр. 4260-4270.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Harvard

Maksimenko, AS, Kislyi, VP, Chernysheva, NB, Strelenko, YA, Zubavichus, YV, Khrustalev, VN, Semenova, MN & Semenov, VV 2019, 'Effective Synthesis of 3,4-Diaryl-isoxazole-5-carboxamides and their Antiproliferative Properties', European Journal of Organic Chemistry, Том. 2019, № 26, стр. 4260-4270. https://doi.org/10.1002/ejoc.201900643

APA

Maksimenko, A. S., Kislyi, V. P., Chernysheva, N. B., Strelenko, Y. A., Zubavichus, Y. V., Khrustalev, V. N., Semenova, M. N., & Semenov, V. V. (2019). Effective Synthesis of 3,4-Diaryl-isoxazole-5-carboxamides and their Antiproliferative Properties. European Journal of Organic Chemistry, 2019(26), 4260-4270. https://doi.org/10.1002/ejoc.201900643

Vancouver

Maksimenko AS, Kislyi VP, Chernysheva NB, Strelenko YA, Zubavichus YV, Khrustalev VN и др. Effective Synthesis of 3,4-Diaryl-isoxazole-5-carboxamides and their Antiproliferative Properties. European Journal of Organic Chemistry. 2019 июль 14;2019(26):4260-4270. doi: 10.1002/ejoc.201900643

Author

Maksimenko, Anna S. ; Kislyi, Victor P. ; Chernysheva, Natalia B. и др. / Effective Synthesis of 3,4-Diaryl-isoxazole-5-carboxamides and their Antiproliferative Properties. в: European Journal of Organic Chemistry. 2019 ; Том 2019, № 26. стр. 4260-4270.

BibTeX

@article{8559e9853e8a44e99152bf1d44e3af41,
title = "Effective Synthesis of 3,4-Diaryl-isoxazole-5-carboxamides and their Antiproliferative Properties",
abstract = "A simple scalable procedure for the synthesis of 3,4-diaryl-isoxazole-5-carboxamides 6 under mild conditions from readily available material was developed. The targeted compounds 6, structural analogues of heat shock protein inhibitors, were obtained by the rearrangement of intermediate 3,4-diaryl-5-carboxamido-isoxazoline N-oxides 5. In contrast to carboxamido-isoxazoline oxides 5, base-catalyzed recyclization of 3,4-diaryl-5-(ethoxycarbonyl)isoxazoline N-oxides 9c unexpectedly yielded 5-hydroxy-1,2-oxazin-6-ones 17c instead of ethyl 3,4-diaryl-isoxazole-5-carboxylates 10. Crystal and molecular structure of 4-(2,5-dimethoxy-3,4-methylenedioxyphenyl)-5-hydroxy-3-phenyl-6H-1,2-oxazin-6-one 17c was established by single-crystal X-ray diffraction study. In a phenotypic sea urchin embryo assay, carboxamide 6f showed moderate antimitotic antitubulin activity compared to 5-unsubstituted 3,4-diarylisoxazoles 15, which featured strong microtubule destabilizing effect.",
keywords = "Antiproliferation, Nitrogen heterocycles, Recyclization, Urchin embryo",
author = "Maksimenko, {Anna S.} and Kislyi, {Victor P.} and Chernysheva, {Natalia B.} and Strelenko, {Yuri A.} and Zubavichus, {Yan V.} and Khrustalev, {Victor N.} and Semenova, {Marina N.} and Semenov, {Victor V.}",
year = "2019",
month = jul,
day = "14",
doi = "10.1002/ejoc.201900643",
language = "English",
volume = "2019",
pages = "4260--4270",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "26",

}

RIS

TY - JOUR

T1 - Effective Synthesis of 3,4-Diaryl-isoxazole-5-carboxamides and their Antiproliferative Properties

AU - Maksimenko, Anna S.

AU - Kislyi, Victor P.

AU - Chernysheva, Natalia B.

AU - Strelenko, Yuri A.

AU - Zubavichus, Yan V.

AU - Khrustalev, Victor N.

AU - Semenova, Marina N.

AU - Semenov, Victor V.

PY - 2019/7/14

Y1 - 2019/7/14

N2 - A simple scalable procedure for the synthesis of 3,4-diaryl-isoxazole-5-carboxamides 6 under mild conditions from readily available material was developed. The targeted compounds 6, structural analogues of heat shock protein inhibitors, were obtained by the rearrangement of intermediate 3,4-diaryl-5-carboxamido-isoxazoline N-oxides 5. In contrast to carboxamido-isoxazoline oxides 5, base-catalyzed recyclization of 3,4-diaryl-5-(ethoxycarbonyl)isoxazoline N-oxides 9c unexpectedly yielded 5-hydroxy-1,2-oxazin-6-ones 17c instead of ethyl 3,4-diaryl-isoxazole-5-carboxylates 10. Crystal and molecular structure of 4-(2,5-dimethoxy-3,4-methylenedioxyphenyl)-5-hydroxy-3-phenyl-6H-1,2-oxazin-6-one 17c was established by single-crystal X-ray diffraction study. In a phenotypic sea urchin embryo assay, carboxamide 6f showed moderate antimitotic antitubulin activity compared to 5-unsubstituted 3,4-diarylisoxazoles 15, which featured strong microtubule destabilizing effect.

AB - A simple scalable procedure for the synthesis of 3,4-diaryl-isoxazole-5-carboxamides 6 under mild conditions from readily available material was developed. The targeted compounds 6, structural analogues of heat shock protein inhibitors, were obtained by the rearrangement of intermediate 3,4-diaryl-5-carboxamido-isoxazoline N-oxides 5. In contrast to carboxamido-isoxazoline oxides 5, base-catalyzed recyclization of 3,4-diaryl-5-(ethoxycarbonyl)isoxazoline N-oxides 9c unexpectedly yielded 5-hydroxy-1,2-oxazin-6-ones 17c instead of ethyl 3,4-diaryl-isoxazole-5-carboxylates 10. Crystal and molecular structure of 4-(2,5-dimethoxy-3,4-methylenedioxyphenyl)-5-hydroxy-3-phenyl-6H-1,2-oxazin-6-one 17c was established by single-crystal X-ray diffraction study. In a phenotypic sea urchin embryo assay, carboxamide 6f showed moderate antimitotic antitubulin activity compared to 5-unsubstituted 3,4-diarylisoxazoles 15, which featured strong microtubule destabilizing effect.

KW - Antiproliferation

KW - Nitrogen heterocycles

KW - Recyclization

KW - Urchin embryo

UR - http://www.scopus.com/inward/record.url?scp=85068522401&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201900643

DO - 10.1002/ejoc.201900643

M3 - Article

AN - SCOPUS:85068522401

VL - 2019

SP - 4260

EP - 4270

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 26

ER -

ID: 25464779