ArticleThe Journal of organic chemistry2016
Characterization and Synthesis of Eudistidine C, a Bioactive Marine Alkaloid with an Intriguing Molecular Scaffold.
Article in The Journal of organic chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 30 citations in OpenAlex.
- Marine Natural Products as Novel Treatments for Parasitic Diseases.Handbook of experimental pharmacology · 2025Review
- Natural Enantiomers: Occurrence, Biogenesis and Biological Properties.Molecules (Basel, Switzerland) · 2022Review
- Demystifying racemic natural products in the homochiral world.Nature reviews. Chemistry · 2022Review
- Marine alkaloids as bioactive agents against protozoal neglected tropical diseases and malaria.Natural product reports · 2021Review
- NMR characterization of rearranged staurosporine aglycone analogues from the marine sponge Damiria sp.Magnetic resonance in chemistry : MRC · 2021Article
- Cytotoxic Naphthoquinone Analogues, Including Heterodimers, and Their Structure Elucidation Using LR-HSQMBC NMR Experiments.Journal of natural products · 2021Article
- Review
- Deciphering the chemical instability of sphaeropsidin A under physiological conditions - degradation studies and structural elucidation of the major metabolite.Organic & biomolecular chemistry · 2020Article
- Elucidation of Spirodactylone, a Polycyclic Alkaloid from the Sponge Dactylia sp., and Nonenzymatic Generation from the Co-metabolite Denigrin B.Organic letters · 2019Article
- Ascidian Toxins with Potential for Drug Development.Marine drugs · 2018Review
- Unequivocal determination of caulamidines A and B: application and validation of new tools in the structure elucidation tool box.Chemical science · 2018Article
Corrections and comments
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Authors and funding
20 authors at 5 institutions in 1 country.
Funding
Abstract
An extract of Eudistoma sp. provided eudistidine C (1), a heterocyclic alkaloid with a novel molecular framework. Eudistidine C (1) is a racemic natural product composed of a tetracyclic core structure further elaborated with a p-methoxyphenyl group and a phenol-substituted aminoimidazole moiety. This compound presented significant structure elucidation challenges due to the large number of heteroatoms and fully substituted carbons. These issues were mitigated by application of a new NMR pulse sequence (LR-HSQMBC) optimized to detect four- and five-bond heteronuclear correlations and the use of computer-assisted structure elucidation software. Synthesis of eudistidine C (1) was accomplished in high yield by treating eudistidine A (2) with 4(2-amino-1H-imidazol-5-yl)phenol (4) in DMSO. Synthesis of eudistidine C (1) confirmed the proposed structure and provided material for further biological characterization. Treatment of 2 with various nitrogen heterocycles and electron-rich arenes provided a series of analogues (5-10) of eudistidine C. Chiral-phase HPLC resolution of epimeric eudistidine C provided (+)-(R)-eudistidine C (1a) and (-)-(S)-eudistidine C (1b). The absolute configuration of these enantiomers was assigned by ECD analysis. (-)-(S)-Eudistidine C (1b) modestly inhibited interaction between the protein binding domains of HIF-1α and p300. Compounds 1, 2, and 6-10 exhibited significant antimalarial activity against Plasmodium falciparum.
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Registered trials
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