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Synthesis and Antiproliferative Activity of Novel Heterocyclic Glycyrrhetinic Acid Derivatives

1
Laboratory of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Coimbra, 3000-548 Coimbra, Portugal
2
Centre for Neuroscience and Cell Biology, 3004-504 Coimbra, Portugal
3
Department of Biochemistry and Molecular Biomedicine, Faculty of Biology, University of Barcelona, Diagonal 643, 08028 Barcelona, Spain
4
Centro de Investigación Biomédica en Red de Enfermedades Hepáticas y Digestivas (CIBEREHD), Instituto de Salud Carlos III (ISCIII), 28029 Madrid, Spain
*
Authors to whom correspondence should be addressed.
Molecules 2019, 24(4), 766; https://doi.org/10.3390/molecules24040766
Received: 16 January 2019 / Revised: 5 February 2019 / Accepted: 15 February 2019 / Published: 20 February 2019
(This article belongs to the Section Medicinal Chemistry)
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Abstract

A new series of glycyrrhetinic acid derivatives has been synthesized via the introduction of different heterocyclic rings conjugated with an α,β-unsaturated ketone in its ring A. These new compounds were screened for their antiproliferative activity in a panel of nine human cancer cell lines. Compound 10 was the most active derivative, with an IC50 of 1.1 µM on Jurkat cells, which is 96-fold more potent than that of glycyrrhetinic acid, and was 4-fold more selective toward that cancer cell line. Further biological studies performed in Jurkat cells showed that compound 10 is a potent inducer of apoptosis that activates both the intrinsic and extrinsic pathways. View Full-Text
Keywords: pentacyclic triterpenoids; glycyrrhetinic acid; heterocyclic derivatives; antiproliferative activity; apoptosis pentacyclic triterpenoids; glycyrrhetinic acid; heterocyclic derivatives; antiproliferative activity; apoptosis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Alho, D.P.S.; Salvador, J.A.R.; Cascante, M.; Marin, S. Synthesis and Antiproliferative Activity of Novel Heterocyclic Glycyrrhetinic Acid Derivatives. Molecules 2019, 24, 766.

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