ArticleThe Journal of organic chemistry2017
Thermal and Photoinduced Copper-Promoted C-Se Bond Formation: Synthesis of 2-Alkyl-1,2-benzisoselenazol-3(2H)-ones and Evaluation against Mycobacterium tuberculosis.
Article in The Journal of organic chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 57 citations in OpenAlex.
- Covalent Inhibitors Targeting Mycobacterial Enzymes: Current Status, Challenges and Future Perspectives.Pharmaceuticals (Basel, Switzerland) · 2026Review
- Selenocyanate-Containing Molecules as Trypanosoma cruzi Inhibitors: Impact of Regioisomerism, Conformational Restriction, and Second-Ring Substitution.ChemMedChem · 2026Article
- Design, Synthesis, and In Vitro Evaluation of 4-(Arylchalcogenyl)methyl)-1H-1,2,3-triazol-1-yl-menadione: Exploring Their Potential AgainstPharmaceuticals (Basel, Switzerland) · 2025Article
- Copper catalyzed carbon-selenium bond formation via the coupling reaction of aryl halides, phenylboronic acid and Se.Scientific reports · 2025Article
- Design and synthesis of novel main protease inhibitors of COVID-19: quinoxalino[2,1-RSC advances · 2024Article
- Asymmetric Synthesis and Applications of Chiral Organoselenium Compounds: A Review.Molecules (Basel, Switzerland) · 2024Review
- Small-Molecule Ebselen Binds to YTHDF Proteins Interfering with the Recognition ofACS pharmacology & translational science · 2022Article
- Magnetic mesocellular foams with nickel complexes: as efficient and reusable nanocatalysts for the synthesis of symmetrical and asymmetrical diaryl chalcogenides.Nanoscale advances · 2022Article
- The Mpro structure-based modifications of ebselen derivatives for improved antiviral activity against SARS-CoV-2 virus.Bioorganic chemistry · 2021Article
- Ebselen and Analogues: Pharmacological Properties and Synthetic Strategies for Their Preparation.Molecules (Basel, Switzerland) · 2021Review
- Neuroprotective and Anti-neuroinflammatory Properties of Ebselen Derivatives and Their Potential to Inhibit Neurodegeneration.ACS chemical neuroscience · 2020Article
- Exploring Covalent Allosteric Inhibition of Antigen 85C from Mycobacterium tuberculosis by Ebselen Derivatives.ACS infectious diseases · 2017Article
Corrections and comments
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Authors and funding
6 authors at 2 institutions in 1 country.
Funding
Abstract
2-Alkyl-1,2-benzisoselenazol-3(2H)-ones, represented by ebselen (1a), are being studied intensively for a range of medicinal applications. We describe both a new thermal and photoinduced copper-mediated cross-coupling between potassium selenocyanate (KSeCN) and N-substituted ortho-halobenzamides to form 2-alkyl-1,2-benzisoselenazol-3(2H)-ones containing a C-Se-N bond. The copper ligand (1,10-phenanthroline) facilitates C-Se bond formation during heating via a mechanism that likely involves atom transfer (AT), whereas, in the absence of ligand, photoinduced activation likely proceeds through a single electron transfer (SET) mechanism. A library of 15 2-alkyl-1,2-benzisoselenazol-3(2H)-ones was prepared. One member of the library was azide-containing derivative 1j that was competent to undergo a strain-promoted azide-alkyne cycloaddition. The library was evaluated for inhibition of Mycobacterium tuberculosis (Mtb) growth and Mtb Antigen 85C (Mtb Ag85C) activity. Compound 1f was most potent with a minimal inhibitory concentration (MIC) of 12.5 μg/mL and an Mtb Ag85C apparent IC
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