ArticleOrganic & biomolecular chemistry2013
A-ring oxygenation modulates the chemistry and bioactivity of caged Garcinia xanthones.
Article in Organic & biomolecular chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
7 citing papers in PubMed, 18 citations in OpenAlex.
- Gambogic acid: Multi-gram scale isolation, stereochemical erosion toward epi-gambogic acid and biological profile.Frontiers in natural products · 2022Article
- Synthetic Chiral Derivatives of Xanthones: Biological Activities and Enantioselectivity Studies.Molecules (Basel, Switzerland) · 2019Review
- Synthesis of 8',11'-dihydrospiro[cyclohexane-1,2'-oxepino[2,3-RSC advances · 2018Article
- Caged Garcinia Xanthones, a Novel Chemical Scaffold with Potent Antimalarial Activity.Antimicrobial agents and chemotherapy · 2017Article
- Gambogic acid identifies an isoform-specific druggable pocket in the middle domain of Hsp90β.Proceedings of the National Academy of Sciences of the United States of America · 2016Article
- Spontaneously-forming spheroids as an in vitro cancer cell model for anticancer drug screening.Oncotarget · 2015Article
- The Fe-S cluster-containing NEET proteins mitoNEET and NAF-1 as chemotherapeutic targets in breast cancer.Proceedings of the National Academy of Sciences of the United States of America · 2015Article
Corrections and comments
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Authors and funding
7 authors at 3 institutions in 2 countries.
Funding
Abstract
Natural products of the caged Garcinia xanthones (CGX) family are characterized by a unique chemical structure, potent bioactivities and promising pharmacological profiles. We have developed a Claisen/Diels-Alder reaction cascade that, in combination with a Pd(0)-catalyzed reverse prenylation, provides rapid and efficient access to the CGX pharmacophore, represented by the structure of cluvenone. To further explore this pharmacophore, we have synthesized various A-ring oxygenated analogues of cluvenone and have evaluated their bioactivities in terms of growth inhibition, mitochondrial fragmentation, induction of mitochondrial-dependent cell death and Hsp90 client inhibition. We found that installation of an oxygen functionality at various positions of the A-ring influences significantly both the site-selectivity of the Claisen/Diels-Alder reaction and the bioactivity of these compounds, due to remote electronic effects.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.