ArticleNature communications2023
2-Oxabicyclo[2.2.2]octane as a new bioisostere of the phenyl ring.
Article in Nature communications, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
What it found
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
14 citing papers in PubMed, 53 citations in OpenAlex.
- Strain-Release Pentafluorosulfanylation of Carbonyl-Containing Disubstituted Bicyclobutanes: A Fortuitous Path to SFAngewandte Chemie (International ed. in English) · 2026Article
- Bicyclo[1.1.1]pentane as a Phenyl Isosteric Replacement.ACS medicinal chemistry letters · 2026Article
- Ladder-shaped molecules for the masses.Nature chemistry · 2026Article
- Complete Computational Exploration of Eight-Carbon Hydrocarbon Chemical Space.The Journal of organic chemistry · 2026Article
- Collective synthesis of 1,2,4-trisubstituted, meta- and ortho-substituted arene bioisosteres from bicyclobutanes.Nature chemistry · 2026Article
- Pharmacokinetics, pathology and efficacy of SARS-CoV-2 main protease inhibitor VPC285785 in a murine model of coronavirus infection.Scientific reports · 2026Article
- Asymmetric C-H Functionalization of Bicyclo[2.1.1]hexanes and Their 2-Oxa- and 2-Aza Derivatives via Rhodium Carbene Intermediates.Journal of the American Chemical Society · 2026Article
- Boron-Enabled Stereoselective Synthesis of Polysubstituted Housanes.Journal of the American Chemical Society · 2025Article
- 3-Oxabicyclo[3.1.1]heptane as an Isostere of meta-Benzene.Angewandte Chemie (International ed. in English) · 2025Article
- Exploring Simple Drug Scaffolds from the Generated Database Chemical Space Reveals a Chiral Bicyclic Azepane with Potent Neuropharmacology.Journal of medicinal chemistry · 2025Article
- Enantioselective photocatalytic synthesis of bicyclo[2.1.1]hexanes as ortho-disubstituted benzene bioisosteres with improved biological activity.Nature chemistry · 2025Article
- Applications of Bridgehead Heterocycles in Drug Design and Medicinal Chemistry.Topics in current chemistry (Cham) · 2025Review
- Modular alkene synthesis from carboxylic acids, alcohols and alkanes via integrated photocatalysis.Nature chemistry · 2024Article
- Three-dimensional saturated C(spNature reviews. Chemistry · 2024Review
Corrections and comments
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Authors and funding
17 authors at 3 institutions in 1 country.
Funding
Abstract
The phenyl ring is a basic structural element in chemistry. Here, we show the design, synthesis, and validation of its new saturated bioisostere with improved physicochemical properties - 2-oxabicyclo[2.2.2]octane. The design of the structure is based on the analysis of the advantages and disadvantages of the previously used bioisosteres: bicyclo[1.1.1]pentane, bicyclo[2.2.2]octane, and cubane. The key synthesis step is the iodocyclization of cyclohexane-containing alkenyl alcohols with molecular iodine in acetonitrile. 2-Oxabicyclo[2.2.2]octane core is incorporated into the structure of Imatinib and Vorinostat (SAHA) drugs instead of the phenyl ring. In Imatinib, such replacement leads to improvement of physicochemical properties: increased water solubility, enhanced metabolic stability, and reduced lipophilicity. In Vorinostat, such replacement results in a new bioactive analog of the drug. This study enhances the repertoire of available saturated bioisosteres of (hetero)aromatic rings for the use in drug discovery projects.
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What OpenQuestion holds
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.