A5056793364- Crystallization and Solubility Studies
- Click Chemistry and Applications
- X-ray Diffraction in Crystallography
- Chemical Synthesis and Analysis
- Radical Photochemical Reactions
- Sulfur-Based Synthesis Techniques
- Catalytic C–H Functionalization Methods
- Synthesis and Characterization of Heterocyclic Compounds
- Catalytic Alkyne Reactions
- Chemical Synthesis and Reactions
- Synthesis of heterocyclic compounds
- Oxidative Organic Chemistry Reactions
- Fluorine in Organic Chemistry
- Computational Drug Discovery Methods
- Catalytic Cross-Coupling Reactions
- Parasitic Infections and Diagnostics
- Toxoplasma gondii Research Studies
- Chemical Reactions and Isotopes
- Synthesis and Reactivity of Sulfur-Containing Compounds
- Synthesis and Biological Evaluation
- Synthesis and Reactions of Organic Compounds
- Antimicrobial Peptides and Activities
- RNA and protein synthesis mechanisms
- interferon and immune responses
- Pneumocystis jirovecii pneumonia detection and treatment
Broad Institute
2020-2024
École Polytechnique Fédérale de Lausanne
2019-2024
Bicyclic azetidines potently inhibit Cryptosporidium in vivo by targeting phenylalanyl-tRNA synthetase.
We report the oxyalkynylation of thiiranes and thietanes using ethynylbenziodoxolone reagents (EBXs) to readily access functionalized building blocks bearing an alkynyl, a benzoate, iodide group. The reaction proceeds with high atom efficiency most likely through alkynyl-episulfonium intermediate. transformation is copper-catalyzed compatible large array thietanes.
We report an azido-alkynylation of alkenes allowing a straightforward access to homopropargylic azides by combining hypervalent iodine reagents and alkynyl-trifluoroborate salts. The design photocatalytic redox-neutral radical polar crossover process was key develop this transformation. A variety possessing electron-rich -poor aryls, heterocycles or ether substituents could be accessed in 34-84% yield. products are synthetically useful building blocks that easily transformed into pyrroles...
We report the detailed background for discovery and development of synthesis homopropargylic azides by azido-alkynylation alkenes. Initially, a strategy involving SOMOphilic alkynes was adopted, but only resulted in 29% yield desired product. By switching to radical-polar crossover approach after optimization, high (72%) azide reached. Full insights are given about factors that were essential success optimization process.
We report a copper-catalyzed alkynylation of azadipeptides using ethynylbenziodoxolone (EBX) reagents. Nonsymmetrical ynehydrazides could be obtained in 25–97% yield azaglycine derivatives as nucleophiles. The transformation is compatible with most functional groups naturally occurring on amino acid side chains and allows the transfer silyl-, alkyl-, aryl-substituted alkynes. α-alkynyl products further functionalized by nucleophilic attack or cycloaddition triple bond.
Ethynylbenziodoxolones (EBXs) are commonly encountered reagents for the electrophilic alkynylation of nucleophiles. Herein, we report a one-pot, two-step process EBX generation and their direct application in substrate functionalization. Our approach enables us to bypass originally mandatory isolation purification reagents, resulting more efficient synthesis. We could apply this seven different transformations involving both two- one-electron nucleophiles obtain large variety alkynylated products.
We report the synthesis of ketene dithioarylacetals in 40–97% yield using thiophenols and acyl-EBXs (ethynylbenziodoxolones) generated situ from a common hypervalent iodine precursor alkynyl trifluoroborate salts. The products could be further modified to afford functionalized dithioacetals various S-substituted heterocycles.
Abstract Previous studies have shown that bicyclic azetidines are potent and selective inhibitors of apicomplexan phenylalanine tRNA synthetase (PheRS), leading to parasite growth inhibition in vitro vivo , including models Toxoplasma infection. Despite these useful properties, additional optimization is required for the development efficacious treatments toxoplasmosis from this inhibitor series, particular achieve sufficient exposure brain. Here, we describe a series PheRS built on new...
Previous studies have shown that bicyclic azetidines are potent and selective inhibitors of apicomplexan phenylalanine tRNA synthetase (PheRS), leading to parasite growth inhibition in vitro vivo, including models Toxoplasma infection. Despite these useful properties, additional optimization is required for the development efficacious treatments toxoplasmosis from this inhibitor series, particular, achieve optimal exposure brain. Here, we describe a series PheRS built on new pyrrolidine core...
We report a copper-catalyzed alkynylation of azadipeptides using ethynylbenziodoxolone (EBX) reagents. Non-symmetrical ynehydrazides could be obtained in 25-97% yield azaglycine derivatives as nucleophiles. The transfor-mation is compatible with most functional groups naturally occurring on amino acid side-chains and allows the transfer silyl-, alkyl- aryl-substituted alkynes. α-alkynyl products further functionalized by nucleophilic attack or cycloaddition triple bond.
We report a copper-catalyzed alkynylation of azadipeptides using ethynylbenziodoxolone (EBX) reagents. Non-symmetrical ynehydrazides could be obtained in 25-97% yield azaglycine derivatives as nucleophiles. The transfor-mation is compatible with most functional groups naturally occurring on amino acid side-chains and allows the transfer silyl-, alkyl- aryl-substituted alkynes. α-alkynyl products further functionalized by nucleophilic attack or cycloaddition triple bond.