ArticleChemistry, an Asian journal2012
Formal synthesis of (-)-englerin A and cytotoxicity studies of truncated englerins.
Article in Chemistry, an Asian journal, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Biological Effects of Modifications of the Englerin A Glycolate.ACS medicinal chemistry letters · 2022Article
- Bridgehead Modifications of Englerin A Reduce TRPC4 Activity and Intravenous Toxicity but not Cell Growth Inhibition.ACS medicinal chemistry letters · 2020Article
- Cycloaddition reactions of enoldiazo compounds.Chemical Society reviews · 2017Review
- Englerins: A Comprehensive Review.Journal of natural products · 2017Review
- Article
- Renal cancer-selective Englerin A induces multiple mechanisms of cell death and autophagy.Journal of experimental & clinical cancer research : CR · 2013Article
- A formal synthesis of (-)-englerin A by relay ring closing metathesis and transannular etherification.Organic letters · 2012Article
- Article
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Authors and funding
5 authors.
Funding
Abstract
An efficient formal synthesis of (-)-englerin A (1) is reported. The target molecule is a recently isolated guaiane sesquiterpene that possesses highly potent and selective activity against renal cancer cell-lines. Our enantioselective strategy involved the construction of the BC ring system of compound 1 through a Rh(II)-catalyzed [4+3] cycloaddition reaction followed by subsequent attachment of the A ring through an intramolecular aldol condensation reaction. As such, this strategy allows the synthesis of truncated englerins. Evaluation of these analogues with the A498 renal cancer cell-line suggested that the A ring of englerin is crucial to its antiproliferative activity. Moreover, evaluation of these analogues led to the identification of potent growth-inhibitors of CEM cells with GI(50) values in the range 1-3 μM.
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Registered trials
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