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A new approach to the synthesis of 17-pyrazolylandrostaneстатья Исследовательская статья
Информация о цитировании статьи получена из
Scopus
Дата последнего поиска статьи во внешних источниках: 1 мая 2024 г.
- Авторы: Komkov Alexander V., Menchikov Leonid G., Dmitrenok Andrey S., Scherbakov Alexander M., Salnikova Diana I., Levina Inna S., Zavarzin Igor V.
- Журнал: Chem. Heterocycl. Compd
- Том: 59
- Номер: 8
- Год издания: 2023
- Первая страница: 554
- Последняя страница: 563
- DOI: 10.1007/s10593-023-03233-8
- Аннотация: We propose a new approach to the synthesis of 17-pyrazolylandrostanes on the basis of 17β-[3-(dimethylamino)acryloyl]-16α,17α-epoxy-3β-hydroxyandrost-5-ene. This epoxyandrostene was shown to react with hydrazine hydrate, producing 17α-hydrazinyl-3β,16α-dihydroxy-17β-(1H-pyrazolyl-3-yl)androst-5-ene that was used in reactions with aromatic aldehydes, leading to 17-hydrazones. The treatment of 17β-[3-(dimethylamino)acryloyl]-16α,17α-epoxy-3β-hydroxyandrost-5-ene with phenylhydrazine led to the formation of 3β,16α-dihydroxy-17-(1-phenyl-1H-pyrazol-5-yl)androst-5-ene. At the same time, the reactions of epoxyandrostene with methylhydrazine or benzylamineproceeded with conservation of the epoxide ring and led to the formation of 16α,17-epoxyandrostanes containing a 1-methyl-1H-pyrazol-5-yl or 3-(benzylamino)acryloyl substituent at position 17, respectively. The obtained hydrazones exhibited a moderate antiproliferativeactivity against the MCF-7 breast cancer cell line. The strongest antiproliferative potential was identified in the case of 17α-[(4-bromobenzylidene)hydrazinyl]-3β,16α-dihydroxy-17β-(1H-pyrazol-3-yl)androst-5-ene with an IC50 value around 16 μM.
- Добавил в систему: Сальникова Диана Игоревна