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Selective synthesis of A-ring <i>Е</i>-arylidene derivatives from β-sitosterol and their activityстатья
- Авторы: Petrova A.V., Khusnutdinova E.F., Lobov A.N., Zakirova L.M., Ha N.T.T, Babkov D.A.
- Журнал: Natural Product Research
- Год издания: 2022
- Издательство: Taylor & Francis
- Местоположение издательства: United Kingdom
- Первая страница: 1
- Последняя страница: 8
- DOI: 10.1080/14786419.2022.2103555
- Аннотация: A series of 24-ethylcholest-4-ene-3,6-dione 2E-arylidene-derivatives has been synthesized by a Claisen-Schmidt reaction from a natural phytosterol β-sitosterol with yields of 80–85%. The structure of the obtained compounds was confirmed by NMR spectroscopy, including two-dimensional correlation experiments. The synthesized compounds were evaluated for their in vitro cytotoxicity and α-glucosidase inhibitory activity. It was established that compound 3 with pyridin-3-ylmethylene moiety exhibited a selective cytotoxic effect against the U251 cancer cell line with 99.31% inhibition of cancer cell growth. Compounds with pyridin-4-ylmethylene 4 and furan-2-ylmethylene-5 fragments were the most active inhibitors of α-glucosidase with IC50 64.00 and 38.95 µM, being 3- and 5-times more active than acarbose. Binding mode to α-glucosidase and ADMET characteristics for the lead molecule 5 were proposed computationally. To sum up, an efficient approach to the derivatives with promising antidiabetic activity based on available natural product β-sitosterol is suggested.
- Добавил в систему: Хуснутдинова Эльмира Фанилевна