ArticleACS medicinal chemistry letters2012
Ring Structure and Aromatic Substituent Effects on the pK a of the Benzoxaborole Pharmacophore.
Article in ACS medicinal chemistry letters, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 37 papers.
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Who cites it
37 citing papers in PubMed.
- Benzoxaboroles Are Structurally Unique Binders of Eukaryotic Translation Initiation Factor 4E.Journal of the American Chemical Society · 2026Article
- Benzoxaboroles are structurally unique binders of eukaryotic translation initiation factor 4E.bioRxiv : the preprint server for biology · 2026Article
- Pharmacology of estrogen-related receptors (ERRs) agonists.RSC chemical biology · 2026Review
- Stereodefined Synthesis of 3-Difluoromethyl-Benzoxaboroles: Novel Antimicrobials with Unlocked H-Bonding.Organic letters · 2026Article
- Formation and Structural Characterization of Benzoxa- and Thienoxaphosphaborinines.The Journal of organic chemistry · 2025Article
- Discovery of an Orally Efficacious Pyrazolo[3,4-Journal of medicinal chemistry · 2025Article
- Experimental and DFT Approaches to Physico-Chemical Properties of Bioactive Resveratrol Analogues.Molecules (Basel, Switzerland) · 2024Article
- The Benzoxazole Heterocycle: A Comprehensive Review of the Most Recent Medicinal Chemistry Developments of Antiproliferative, Brain-Penetrant, and Anti-inflammatory Agents.Topics in current chemistry (Cham) · 2024Review
- Boronate Ester Hydrogels for Biomedical Applications: Challenges and Opportunities.Chemistry of materials : a publication of the American Chemical Society · 2024Review
- Applications of chromatographic methods in metabolomics: A review.Journal of chromatography. B, Analytical technologies in the biomedical and life sciences · 2024Review
- Modular Synthesis of Complex Benzoxaboraheterocycles through Chelation-Assisted Rh-Catalyzed [2 + 2 + 2] Cycloaddition.ACS catalysis · 2024Article
- Review
- Correlations between the Electronic Structure and Energetics of the Catalytic Steps in Homogeneous Water Oxidation Catalysis.Journal of the American Chemical Society · 2023Article
- Synthesis and Biophysical and Biological Studies ofJournal of medicinal chemistry · 2023Article
- An endoscopically compatible fast-gelation powder forms Janus-adhesive hydrogel barrier to prevent postoperative adhesions.Proceedings of the National Academy of Sciences of the United States of America · 2023Article
- Merging Electron Deficient Boronic Centers with Electron-Withdrawing Fluorine Substituents Results in Unique Properties of Fluorinated Phenylboronic Compounds.Molecules (Basel, Switzerland) · 2022Review
- Reactive chemistry for covalent probe and therapeutic development.Trends in pharmacological sciences · 2022Review
- How Substitution Combines with Non-Covalent Interactions to Modulate 1,4-Naphthoquinone and Its Derivatives Molecular Features-Multifactor Studies.International journal of molecular sciences · 2021Article
- Development of structurally extended benzosiloxaboroles - synthesis andRSC advances · 2021Article
- Boronic acid with high oxidative stability and utility in biological contexts.Proceedings of the National Academy of Sciences of the United States of America · 2021Article
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Authors and funding
4 authors.
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Abstract
In this work, we present an investigation into the physical properties of a unique class of aromatic boronic acids, the benzoxaboroles. Using spectrophotometric methods, the ionization constants of a family of substituted benzoxaboroles are determined. Heterocyclic ring modifications are examined to determine their effects on the ionization of the boronic acid moiety. It is also shown that the substituent effects about the aromatic ring follow a Hammett relationship with the compounds' measured pK a values. Finally, these substituent effects are also shown to extend to the sugar binding properties of these compounds under physiologically relevant conditions. Combined, these data will inform medicinal chemists wishing to tailor the ionization and/or ability of this class of compound to bind diol-containing biomolecules.
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