Open Access
Molecules, volume 25, issue 15, pages 3499
Novel d-annulated pentacyclic steroids: Regioselective synthesis and biological evaluation in breast cancer cells
Yadykov Anton V
1
,
Minyaev Mikhail E.
1
,
Zavarzin Igor V
1
,
Mikhaevich Ekaterina I
2
,
Volkova Yulia
1
,
Shirinian Valerii Z
1
Publication type: Journal Article
Publication date: 2020-07-31
PubMed ID:
32752019
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
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.
Citations by journals
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1
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CrystEngComm
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1 publication, 14.29%
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Investigational New Drugs
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1 publication, 14.29%
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Physical Chemistry Chemical Physics
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Citations by publishers
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1
2
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Royal Society of Chemistry (RSC)
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Royal Society of Chemistry (RSC)
2 publications, 28.57%
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Springer Nature
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Springer Nature
1 publication, 14.29%
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Multidisciplinary Digital Publishing Institute (MDPI)
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Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 14.29%
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Elsevier
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Elsevier
1 publication, 14.29%
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Wiley
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Wiley
1 publication, 14.29%
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1
2
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- We do not take into account publications that without a DOI.
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- Statistics recalculated weekly.
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Vorontsova S. K. et al. Novel d-annulated pentacyclic steroids: Regioselective synthesis and biological evaluation in breast cancer cells // Molecules. 2020. Vol. 25. No. 15. p. 3499.
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Vorontsova S. K., Yadykov A. V., Scherbakov A. M., Minyaev M. E., Zavarzin I. V., Mikhaevich E. I., Volkova Y., Shirinian V. Z. Novel d-annulated pentacyclic steroids: Regioselective synthesis and biological evaluation in breast cancer cells // Molecules. 2020. Vol. 25. No. 15. p. 3499.
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TY - JOUR
DO - 10.3390/molecules25153499
UR - https://doi.org/10.3390%2Fmolecules25153499
TI - Novel d-annulated pentacyclic steroids: Regioselective synthesis and biological evaluation in breast cancer cells
T2 - Molecules
AU - Vorontsova, Svetlana K
AU - Minyaev, Mikhail E.
AU - Zavarzin, Igor V
AU - Mikhaevich, Ekaterina I
AU - Yadykov, Anton V
AU - Shirinian, Valerii Z
AU - Scherbakov, Alexander M.
AU - Volkova, Yulia
PY - 2020
DA - 2020/07/31 00:00:00
PB - Multidisciplinary Digital Publishing Institute (MDPI)
SP - 3499
IS - 15
VL - 25
PMID - 32752019
SN - 1420-3049
ER -
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@article{2020_Vorontsova,
author = {Svetlana K Vorontsova and Mikhail E. Minyaev and Igor V Zavarzin and Ekaterina I Mikhaevich and Anton V Yadykov and Valerii Z Shirinian and Alexander M. Scherbakov and Yulia Volkova},
title = {Novel d-annulated pentacyclic steroids: Regioselective synthesis and biological evaluation in breast cancer cells},
journal = {Molecules},
year = {2020},
volume = {25},
publisher = {Multidisciplinary Digital Publishing Institute (MDPI)},
month = {jul},
url = {https://doi.org/10.3390%2Fmolecules25153499},
number = {15},
pages = {3499},
doi = {10.3390/molecules25153499}
}
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MLA
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Vorontsova, Svetlana K., et al. “Novel d-annulated pentacyclic steroids: Regioselective synthesis and biological evaluation in breast cancer cells.” Molecules, vol. 25, no. 15, Jul. 2020, p. 3499. https://doi.org/10.3390%2Fmolecules25153499.