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.
Highlights
Triterpenoids are a large group of natural compounds that are widely found in nature and are prevalent in plants
The synthesis of three pairs of novel Glycyrrhetinic acid (GA) 1 heterocyclic derivatives is summarized in Scheme 1
In addition to the intention to prepare heterocyclic derivatives with improved cytotoxicity, 9–14 were synthesized to explore the effect of the keto group in position C-11 on the antiproliferative compounds 9–14 were synthesized to explore the effect of the keto group in position C-11 on the activity
Summary
Triterpenoids are a large group of natural compounds that are widely found in nature and are prevalent in plants They display a wide spectrum of biological and pharmacological activities. Glycyrrhetinic acid (GA) 1 (Figure 1) is the aglycone of glycyrrhizin, a major pentacyclic triterpenoid saponin found in the roots of licorice (Glycyrrhiza species) [12] This compound has a proven antiproliferative activity against several cancer cell lines and its anticancer effects were observed in animal models [13,14,15,16]. GA 1 can be extracted from the roots of licorice in high yields (up to 24%) [22] These findings have increased its scientific interest as a scaffold for the development of new derivatives for potential cancer treatment [23,24,25,26,27]
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