Реферат: The acid-catalyzed cyclization of benzylidenes based on 16-dehydropregnenolone acetate (16-DPA) was studied. It was found that these compounds readily undergo regioselective interrupted Nazarov cyclization with trapping chloride ion and an efficient method of the synthesis of d-annulated pentacyclic steroids based on this reaction was proposed. The structures of the synthesized pentacyclic steroids were determined by NMR and X-ray diffraction. It was found that the reaction affords a single diastereomer, but the latter can crystallize as two conformers depending on the structure. Antiproliferative activity of synthesized compounds was evaluated against two breast cancer cell lines: MCF-7 and MDA-MB-231. All tested compounds showed relatively high antiproliferative activity. The synthetic potential of the protocol developed was illustrated by the gram-scale experiment.

Библиографическая ссылка: Vorontsova S.K. , Yadykov A.V. , Scherbakov A.M. , Minyaev M.E. , Zavarzin I.V. , Mikhaevich E.I. , Volkova Y.A. , Shirinian V.Z.
Novel d-Annulated Pentacyclic Steroids: Regioselective Synthesis and Biological Evaluation in Breast Cancer Cells
Molecules. 2020. V.25. N15. 3499 . DOI: 10.3390/molecules25153499 WOS Scopus OpenAlex

Идентификаторы БД:

Web of science:	WOS:000567239300001
Scopus:	2-s2.0-85089130688
OpenAlex:	W3046416756

Цитирование в БД:

БД	Цитирований
OpenAlex	10
Scopus	7
Web of science	6

Альметрики: