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

Anna S. Maksimenko, Victor P. Kislyi, Natalia B. Chernysheva, Yuri A. Strelenko, Yan V. Zubavichus, Victor N. Khrustalev, Marina N. Semenova, Victor V. Semenov

Результат исследования: Научные публикации в периодических изданияхстатья

1 Цитирования (Scopus)

Аннотация

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.

Язык оригиналаанглийский
Страницы (с-по)4260-4270
Число страниц11
ЖурналEuropean Journal of Organic Chemistry
Том2019
Номер выпуска26
DOI
СостояниеОпубликовано - 14 июл 2019
Опубликовано для внешнего пользованияДа

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  • Цитировать

    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