Novel d-Annulated Pentacyclic Steroids: Regioselective Synthesis and Biological Evaluation in Breast Cancer Cells Full article
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Molecules
ISSN: 1420-3049 |
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| Output data | Year: 2020, Volume: 25, Number: 15, Article number : 3499, Pages count : DOI: 10.3390/molecules25153499 | ||||
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Abstract:
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.
Cite:
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
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
Identifiers:
| Web of science: | WOS:000567239300001 |
| Scopus: | 2-s2.0-85089130688 |
| OpenAlex: | W3046416756 |