Effective Synthesis of 3,4-Diaryl-isoxazole-5-carboxamides and their Antiproliferative Properties Научная публикация
Журнал |
European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690 |
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Вых. Данные | Год: 2019, Том: 2019, Номер: 26, Страницы: 4260-4270 Страниц : 11 DOI: 10.1002/ejoc.201900643 | ||||||||
Ключевые слова | Nitrogen heterocycles · Recyclization ·Antiproliferation · Urchin embryo | ||||||||
Авторы |
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Организации |
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Реферат:
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.
Библиографическая ссылка:
Maksimenko A.S.
, Kislyi V.P.
, Chernysheva N.B.
, Strelenko Y.A.
, Zubavichus Y.V.
, Khrustalev V.N.
, Semenova M.N.
, Semenov V.V.
Effective Synthesis of 3,4-Diaryl-isoxazole-5-carboxamides and their Antiproliferative Properties
European Journal of Organic Chemistry. 2019. V.2019. N26. P.4260-4270. DOI: 10.1002/ejoc.201900643 WOS Scopus РИНЦ
Effective Synthesis of 3,4-Diaryl-isoxazole-5-carboxamides and their Antiproliferative Properties
European Journal of Organic Chemistry. 2019. V.2019. N26. P.4260-4270. DOI: 10.1002/ejoc.201900643 WOS Scopus РИНЦ
Даты:
Поступила в редакцию: | 30 апр. 2019 г. |
Опубликована online: | 4 июл. 2019 г. |
Опубликована в печати: | 14 июл. 2019 г. |
Идентификаторы БД:
Web of science | WOS:000474190300001 |
Scopus | 2-s2.0-85068522401 |
РИНЦ | 41635652 |
Chemical Abstracts | 2019:1329981 |
Chemical Abstracts (print) | 171:302273 |
OpenAlex | W2953476189 |