ArticleJournal of the American Chemical Society2017
Quantitative Modeling of Bis(pyridine)silver(I) Permanganate Oxidation of Hydantoin Derivatives: Guidelines for Predicting the Site of Oxidation in Complex Substrates.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 22 citations in OpenAlex.
- Total Synthesis and Anticancer Study of (+)-Verticillin A.Journal of the American Chemical Society · 2025Article
- Computational tools for the prediction of site- and regioselectivity of organic reactions.Chemical science · 2025Review
- Total synthesis of complex 2,5-diketopiperazine alkaloids.The Alkaloids. Chemistry and biology · 2023Review
- Article
- Structure-Activity Relationship Studies of Hydantoin-Cored Ligands for Smoothened Receptor.ChemistryOpen · 2021Article
- Article
- Appraisal of disease-modifying potential of amlodipine as an anti-arthritic agent: new indication for an old drug.Inflammopharmacology · 2020Article
- Synthesis of Potent Cytotoxic Epidithiodiketopiperazines Designed for Derivatization.The Journal of organic chemistry · 2020Article
- An unknown component of a selective and mild oxidant: structure and oxidative ability of a double salt-type complex having κRSC advances · 2019Article
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
Abstract
The bis(pyridine)silver(I) permanganate promoted hydroxylation of diketopiperazines has served as a pivotal transformation in the synthesis of complex epipolythiodiketopiperazine alkaloids. This late-stage C-H oxidation chemistry is strategically critical to access N-acyl iminium ion intermediates necessary for nucleophilic thiolation of advanced diketopiperazines en route to potent epipolythiodiketopiperazine anticancer compounds. In this study, we develop an informative mathematical model using hydantoin derivatives as a training set of substrates by relating the relative rates of oxidation to various calculated molecular descriptors. The model prioritizes Hammett values and percent buried volume as key contributing factors in the hydantoin series while correctly predicting the experimentally observed oxidation sites in various complex diketopiperazine case studies. Thus, a method is presented by which to use simplified training molecules and resulting correlations to explain and predict reaction behavior for more complex substrates.
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