4.6 Review

Chemoselective Reactions of Functionalized Sulfonyl Halides

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Diversity oriented clicking delivers ?-substituted alkenyl sulfonyl fluorides as covalent human neutrophil elastase inhibitors br

Yunfei Cheng et al.

Summary: Diversity Oriented Clicking (DOC) is a method for rapidly synthesizing functional libraries by combining classical and modern click chemistries. It involves modulating the assembly of compounds through chemical diversification of core SuFExable hubs, such as 2-Substituted-Alkynyl-1-Sulfonyl Fluorides (SASFs). The stereoselective Michael-type addition reactions from SASF hubs, including reactions with secondary amines, carboxylates, 1H-1,2,3-triazole, and halides, provide high yielding beta-substituted alkenyl sulfonyl fluorides as single isomers with minimal purification. These compounds show potential as covalent inhibitors of human neutrophil elastase, demonstrating the biological function aspect of click chemistry.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2022)

Article Biochemistry & Molecular Biology

Design, synthesis and biological evaluation of 2-aminopyridine derivatives as USP7 inhibitors

Xiaoming Xu et al.

Summary: A series of novel 2-aminopyridine derivatives were synthesized and evaluated for their USP7 inhibitory activities. Compounds 7 and 21 showed significant binding interactions with USP7 according to surface plasmon resonance binding assay.

BIOORGANIC CHEMISTRY (2022)

Article Chemistry, Organic

A reductive dehalogenative process for chemo- and stereoselective synthesis of 1,3-dienylsulfonyl fluorides

Yu-Zhen Zeng et al.

Summary: A mild and efficient method for the synthesis of 1,3-dienylsulfonyl fluorides was developed via dehalogenation of alpha-halo-1,3-dienylsulfonyl fluorides using zinc powder and acetic acid. Exclusive chemo- and stereoselectivities were achieved. This protocol was successfully applied to the synthesis of heterocyclic dienylsulfonyl fluorides and polyene sulfonyl fluoride.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Palladium-catalyzed C-H olefination of uridine, deoxyuridine, uridine monophosphate and uridine analogues

Qin Zhao et al.

Summary: The palladium-catalyzed oxidative C-H olefinations of uridine, deoxyuridine, uridine monophosphate and uridine analogues are reported. This protocol offers an efficient, atom-economic, and environmentally friendly approach for synthesizing biologically important C5-alkene modified uracil/uridine-containing derivatives and pharmaceutical candidates.

RSC ADVANCES (2022)

Review Chemistry, Multidisciplinary

Copper-photocatalyzed ATRA reactions: concepts, applications, and opportunities

Sebastian Engl et al.

Summary: Atom transfer radical addition (ATRA) reactions are important transformations in synthetic chemistry for the difunctionalization of alkenes using simple starting materials. The recent advancement in photocatalysis, particularly using copper complexes, has provided a mild and energy-efficient alternative to the traditional methods that required toxic initiators or harsh thermal conditions. Copper photocatalysis has the advantage of enabling ligand exchange and facilitating transformations utilizing their coordination sphere. It also allows the access to two-component and three-component ATRA reactions that were not feasible with other catalysts like ruthenium or iridium. This review highlights the emerging field of using Cu(i)-substrate assemblies as active photocatalysts for achieving three-component coupling reactions under enantioselective control.

CHEMICAL SOCIETY REVIEWS (2022)

Article Chemistry, Organic

Regioselective conjugate addition of isoxazol-5-ones to ethenesulfonyl fluoride

Dong-yu Zhu et al.

Summary: A highly regioselective conjugate addition of isoxazol-5-ones to ethenesulfonyl fluoride (ESF) has been developed, yielding N2-alkylated and C4-alkylated isoxazol-5-ones with a sulfonyl fluoride group. Further transformations with amines and phenol give sulfonamides and sulfonates, providing valuable products for drug discovery.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Article Chemistry, Organic

A cascade reaction for regiosetective construction of pyrazole-containing aliphatic sulfonyl fluorides

Wen-Fei Yang et al.

Summary: A copper-catalyzed cascade reaction has been developed for the synthesis of highly functionalized pyrazolyl aliphatic sulfonyl fluorides in good yields. This method demonstrates broad substrate compatibility, exclusive regioselectivity, high atom economy, and operational simplicity, making it valuable for the direct construction of pyrazole-containing aliphatic sulfonyl fluorides in medicinal chemistry and related disciplines.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Article Chemistry, Medicinal

Synthesis and Structure-activity Relationship of Aminoarylthiazole Derivatives as Potential Potentiators of the Chloride Transport Defect in Cystic Fibrosis

Nara Liessi et al.

Summary: Cystic fibrosis is a common genetic disorder caused by mutations in the CFTR protein. Some aminoarylthiazoles have been identified as correctors and potentiators for CFTR, with compounds 2 and 13 showing promise for future development as potentiators for chloride transport defects in cystic fibrosis.

MEDICINAL CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Electrochemical Oxo-Fluorosulfonylation of Alkynes under Air: Facile Access to β-Keto Sulfonyl Fluorides

Dengfeng Chen et al.

Summary: This study reports a new electrochemical method for generating FSO2 radicals and synthesizing beta-keto sulfonyl fluorides, which can yield two different products through oxo-fluorosulfonylation. These products can be used as building blocks for various derivatives and heterocycles, exhibiting potent activities against Bursaphelenchus xylophilus and Colletotrichum gloeosporioides.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Desulfonative Suzuki-Miyaura Coupling of Sulfonyl Fluorides

Paul Chatelain et al.

Summary: Sulfonyl fluorides have been identified as powerful click electrophiles for Pd-catalyzed Suzuki-Miyaura cross-coupling, occurring selectively in the absence of base and even in the presence of strong acids. Mechanistic experiments and DFT calculations suggest that oxidative addition at the C-S bond followed by desulfonation facilitate transmetalation in this desulfonative cross-coupling reaction.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

A Broad-Spectrum Catalytic Amidation of Sulfonyl Fluorides and Fluorosulfates**

Mingjie Wei et al.

Summary: A catalytic method has been developed for the synthesis of sulfonamides and sulfamates with the activation by 1-hydroxybenzotriazole (HOBt) and silicon additives, showing high efficiency for sterically hindered substrates. The catalyst loading is low and yields are generally excellent, demonstrating potential applications in medicinal chemistry.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Iminoboronates as Dual-Purpose Linkers in Chemical Probe Development

Antonie J. van der Zouwen et al.

Summary: Chemical probes that covalently modify proteins are powerful tools for biological research. Choosing the right reactive group for the design of a probe is crucial, and a modular approach has been developed in this study for easy coupling of reactive groups to ligands. The iminoboronate probes synthesized in this study selectively label target proteins and can be further modified using transimination reactions with aminohydrazides, for example, to introduce fluorophores.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Article Chemistry, Organic

I2-Promoted Direct C-H Sulfenylation of Isoquinolin-1(2H)-ones with Sulfonyl Chlorides

Cai-Yun Yang et al.

Summary: A simple, efficient, and green method for regioselective C-4 sulfenylation of isoquinolin-1(2H)-ones was described using aryl sulfonyl chlorides as the sulfur source under metal- and solvent-free conditions. The reaction showed high regioselectivity, broad substrate scope, and good functional group tolerance, and a radical reaction mechanism involving ArS. radicals as key intermediates was proposed.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Medicinal

Discovery of GLPG2451, a Novel Once Daily Potentiator for the Treatment of Cystic Fibrosis

Steven E. Van der Plas et al.

Summary: Cystic fibrosis is a life-threatening disease caused by mutations in the CFTR gene, but its function can be partially restored with correctors and potentiators. The discovery and optimization of a novel potentiator series focused on retaining different intramolecular contacts to identify a series devoid of genotoxic liabilities. The clinical candidate GLPG2451 was chosen based on its pharmacokinetic properties and low CYP induction potential.

JOURNAL OF MEDICINAL CHEMISTRY (2021)

Article Chemistry, Organic

The synthesis of chiral β-naphthyl-β-sulfanyl ketones via enantioselective sulfa-Michael reaction in the presence of a bifunctional cinchona/sulfonamide organocatalyst

Deniz Tozendemir et al.

Summary: Cinchona alkaloid-derived organocatalysts have been widely utilized in asymmetric transformations, resulting in products with high enantiopurity. A bifunctional quinine-derived sulfonamide organocatalyst was developed for catalyzing the asymmetric sulfa-Michael reaction, achieving high enantioselectivity with low catalyst loading. The enriched sulfa-Michael addition products were successfully oxidized to obtain the corresponding sulfones.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Biochemistry & Molecular Biology

Design, synthesis, spectral characterization and molecular docking studies of novel pyranoquinolinyl dihydropyridine carboxylates as potential antibacterial agents including Vibrio cholerae with minimal cytotoxity towards fibroblast cell line (L-929)

G. Lavanya et al.

Summary: Novel pyranoquinolinyl dihydropyridine carboxylate (PDC) derivatives with potential antibacterial activity were designed and synthesized, showing good in vitro antibacterial activity and molecular docking mechanism. The study highlights the potential antimicrobial properties of the PDC derivatives.

BIOORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Highly Enantioselective Addition of N-2,2,2-Trifluoroethylisatin Ketimines to Ethylene Sulfonyl Fluoride

Jie Chen et al.

Summary: An enantioselective Michael addition has been developed for the synthesis of structurally diverse isatin-derived alpha-(trifluoromethyl)imine derivatives with excellent yields and enantioselectivities, which are valuable candidates for drug discovery.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Acetal Addition to Electron-Deficient Alkenes with Hydrogen Atom Transfer as a Radical Chain Propagation Step

Wei Chuen Chan et al.

Summary: In this study, a visible-light-promoted addition reaction utilizing a hydrogen atom and an acetal carbon towards various electron-deficient alkenes was described. The reaction operates via a radical chain mechanism, which is a less commonly observed pathway for this type of transformation. Experimental and density functional theory studies confirmed the hydrogen atom transfer from 1,3-dioxolane to alpha-malonyl radicals.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Design, synthesis, and antibacterial activity of novel myricetin derivatives containing sulfonate

Shijun Su et al.

Summary: A series of myricetin derivatives containing sulfonate groups were designed and synthesized, showing significant antibacterial activities against various plant pathogenic bacteria. Some compounds demonstrated better activities than commercial reagents, suggesting their potential as new antibacterial agents.

MONATSHEFTE FUR CHEMIE (2021)

Article Biochemistry & Molecular Biology

Discovery of a Cell-Active SuTEx Ligand of Prostaglandin Reductase 2

Emmanuel K. Toroitich et al.

Summary: The study demonstrated the potential of SuTEx compounds in covalent modification of protein tyrosine sites and identified HHS-0701 as a cell-active inhibitor targeting prostaglandin reductase 2.

CHEMBIOCHEM (2021)

Article Chemistry, Multidisciplinary

Cu-catalyzed endo-selective asymmetric 1,3-dipolar cycloaddition of azomethine ylides with ethenesulfonyl fluorides: Efficient access to chiral pyrrolidine-3-sulfonyl fluorides

Yi-Nan Li et al.

Summary: The Cu-catalyzed endo-selective asymmetric 1,3-dipolar cycloaddition of azomethine ylides with ethenesulfonyl fluorides (ESFs) provides an efficient method to access a wide range of chiral pyrrolidine-3-sulfonyl fluorides and other chiral sulfonyl derivatives with good yields and stereoselectivity, demonstrating their synthetic utility in SuFEx chemistry.

CHINESE CHEMICAL LETTERS (2021)

Article Chemistry, Organic

Heteroaliphatic Dimethylphosphine Oxide Building Blocks: Synthesis and Physico-Chemical Properties

Andrii Fedyk et al.

Summary: The scalable synthesis of saturated heterocyclic dimethyl phosphine oxides was achieved through key steps involving reactions of HP(O)Me-2, palladium-catalyzed reactions, and base-mediated nucleophilic substitutions. Introduction of the P(O)Me-2 group significantly affected the compound's basicity, hydrophilicity, and aqueous solubility. This method shows potential for generating lead-like three-dimensional compound libraries as confirmed using the LLAMA tool.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Review Chemistry, Organic

Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances

Oleksandr O. Grygorenko et al.

Summary: Current medicinal chemistry heavily relies on the quality of building blocks, with an emergence of many novel (or well-overlooked) chemotypes for drug discovery. This includes adapting new synthetic methodologies, designing new bioisosteres, and paying attention to underrated structural motifs.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Medicinal

An Exploration of Chemical Properties Required for Cooperative Stabilization of the 14-3-3 Interaction with NF-κB-Utilizing a Reversible Covalent Tethering Approach

Madita Wolter et al.

Summary: This study describes the systematic bottom-up development of a reversible covalent PPI stabilizer and investigates how its chemical properties affect the structural changes in the ternary 14-3-3/p65/molecular glue complex, ultimately leading to increased stability and high cooperativity.

JOURNAL OF MEDICINAL CHEMISTRY (2021)

Article Chemistry, Medicinal

Development of Covalent, Clickable Probes for Adenosine A1 and A3 Receptors

Phuc N. H. Trinh et al.

Summary: This study presents the development of the first bifunctional ligands for adenosine A(1) receptor and adenosine A(3) receptor, which possess nanomolar affinity and irreversible binding properties. These ligands can aid in target validation and direct visualization of receptors in different native environments. They also exhibit moderate selectivity over A(2A) and A(2B) adenosine receptors.

JOURNAL OF MEDICINAL CHEMISTRY (2021)

Article Biochemistry & Molecular Biology

Nucleus-Independent Chemical Shift (NICS) as a Criterion for the Design of New Antifungal Benzofuranones

Maria de los Angeles Zermeno-Macias et al.

Summary: The study indicates that aromaticity plays an important role in molecular design, and the use of nucleus-independent chemical shifts (NICS) is an effective criterion for evaluating the antifungal activity of indol-4-ones. A linear regression analysis showed a significant relationship between NICS and antifungal activity, with varying effects on different series of compounds. Furthermore, the validity of the equations was confirmed through the synthesis and testing of benzofuran-4-ones, supporting the utility of NICS in the molecular design of compounds with antifungal activity.

MOLECULES (2021)

Article Chemistry, Organic

SuFExable Isocyanides for Ugi Reaction: Synthesis of Sulfonyl Fluoro Peptides

Shuheng Xu et al.

Summary: The sulfonyl fluoro isocyanides were developed as a new type of SuFExable synthon and utilized as building blocks in the Ugi reaction. This study established the Ugi reaction and explored its substrate scope, allowing for the one-step synthesis of various sulfonyl fluoro alpha-amino amides and peptides. This protocol presents a novel approach for SuFExable building blocks and click chemistry, as well as offering a distinct method for sulfonyl fluoro peptides.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Enantioselective Addition of Azlactones to Ethylene Sulfonyl Fluoride via Dual Catalysis

Dong-yu Zhu et al.

Summary: Enantioselective conjugate addition of azlactones to ethylene sulfonyl fluoride has been achieved effectively via cooperative catalysis, providing structurally diverse azlactone sulfonyl fluoride derivatives for drug discovery purposes.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Transition metal-free regioselective synthesis of triazolyl aliphatic sulfonyl fluorides

Shadrack Wilson Lucas et al.

Summary: An efficient and metal-free method has been developed for exclusively regioselective construction of aliphatic sulfonyl fluoride moiety at the C4 position of 1,2,3-triazole ring in up to 95 % isolated yield.

TETRAHEDRON (2021)

Article Biochemistry & Molecular Biology

Structure-activity relationship, in vitro and in vivo evaluation of novel dienyl sulphonyl fluorides as selective BuChE inhibitors for the treatment of Alzheimer's disease

Chengyao Wu et al.

Summary: Compound A10, as a selective BuChE inhibitor, exhibits neuroprotective effects, good safety profile, and can effectively restore Aβ (1-42)-induced cognitive dysfunction.

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Radical-mediated vicinal addition of alkoxysulfonyl/fluorosulfonyl and trifluoromethyl groups to aryl alkyl alkynes

Xinrui Dong et al.

Summary: The addition of trifluoromethyl sulfonyl radicals to alkynes is a valuable method for constructing highly functionalized sulfonyl compounds. This process shows broad functional group compatibility and potential in drug discovery and chemical biology.

CHEMICAL SCIENCE (2021)

Article Chemistry, Organic

A general approach to nitrile- and sulfonyl fluoride-substituted cyclopropanes

Zai-Wei Zhang et al.

Summary: Both cis and trans configurations of functionalized cyano cyclopropane bearing sulfonyl fluoride moiety can be accessed through Corey-Chaykovsky cyclopropanation reactions. This protocol is mild and leads to good yields with excellent functional group compatibility. Further applications of these compounds in SuFEx reactions and cyano reductions have also been successfully achieved in good yields.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Photoredox-catalyzed aminofluorosulfonylation of unactivated olefins

Tao Zhong et al.

Summary: This study successfully reported the first three-component aminofluorosulfonylation of unactivated olefins by merging photoredox-catalyzed proton-coupled electron transfer (PCET) activation with radical relay processes, efficiently affording various aliphatic sulfonyl fluorides featuring a privileged 5-membered heterocyclic core under mild conditions with good functional group tolerance. The synthetic potential of the sulfonyl fluoride products was examined by diverse transformations including SuFEx reactions and transition metal-catalyzed cross-coupling reactions, with mechanistic studies demonstrating the involvement of amidyl radicals, alkyl radicals, and sulfonyl radicals in this difunctionalization transformation.

CHEMICAL SCIENCE (2021)

Article Chemistry, Multidisciplinary

Photoactive electron donor-acceptor complex platform for Ni-mediated C(sp3)-C(sp2) bond formation

Lisa Marie Kammer et al.

Summary: A dual photochemical/nickel-mediated decarboxylative strategy for the assembly of C(sp(3))-C(sp(2)) linkages has been developed. This platform utilizes commercially available Hantzsch ester as an organic photoreductant to generate catalytically active Ni(0) species under light irradiation, enabling the coupling of diverse C(sp(3))-centered radical architectures with (hetero)aryl bromides. The protocol proceeds under mild reaction conditions and is compatible with sensitive functional groups and pharmaceutically relevant cores.

CHEMICAL SCIENCE (2021)

Article Chemistry, Organic

Design, synthesis, and evaluation of positron emission tomography/fluorescence dual imaging probes for targeting facilitated glucose transporter 1 (GLUT1)

Richard Yuen et al.

Summary: The study aimed to develop novel glucose-based dual imaging probes for PET and fluorescence imaging. Among the compounds tested, 2-FBDG showed favorable fluorescent properties and similar potency to 2-NBDG in competing for GLUT1 transport in breast cancer cells.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Arylation of gem-difluoroalkenes using a Pd/Cu Co-catalytic system that avoids β-fluoride elimination

Kedong Yuan et al.

Summary: In the arylation reaction of gem-difluoroalkenes using arylsulfonyl chlorides catalyzed by Pd-II/Cu-I, an alternate low-energy route involving beta-H elimination is proposed to avoid beta-F elimination, leading to the synthesis of difluorinated products. This reaction allows exploration of new reactivities of unstable fluorinated alkyl-metal species, and provides new opportunities for transforming readily available fluorinated alkenes into more elaborate substructures.

CHEMICAL SCIENCE (2021)

Article Chemistry, Multidisciplinary

Molecular design principles of ionic liquids with a sulfonyl fluoride moiety

David J. Siegel et al.

Summary: A new method for developing sulfonyl fluoride-functionalized ionic liquids with structural diversity has been reported. These ionic liquids exhibit properties consistent with their classification as ionic liquids. In-depth understanding of structure-property correlations was gained through a combination of methods including molecular design, synthesis, computational modeling, and X-ray crystallographic studies.

NEW JOURNAL OF CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Metal-Free Synthesis of Functional 1-Substituted-1,2,3-Triazoles from Ethenesulfonyl Fluoride and Organic Azides

Marie-Claire Giel et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Ligand Conformational Bias Drives Enantioselective Modification of a Surface-Exposed Lysine on Hsp90

Adolfo Cuesta et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Organic

Arylsulfonyl fluoride boronic acids: Preparation and coupling reactivity

Terry Shing-Bong Lou et al.

TETRAHEDRON (2020)

Article Chemistry, Medicinal

Discovery of Isoxazole Amides as Potent and Selective SMYD3 Inhibitors

Dai-Shi Su et al.

ACS MEDICINAL CHEMISTRY LETTERS (2020)

Article Chemistry, Multidisciplinary

Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) Hubs

Christopher J. Smedley et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Chemistry, Organic

Recent Advances of Sulfonylation Reactions in Water

Li Wu et al.

CURRENT ORGANIC SYNTHESIS (2020)

Article Chemistry, Organic

Synthesis of Functionalized Bridged Bicyclic Sulfonamides with a Bridgehead Nitrogen Atom

Oleksandr P. Blahun et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Organic

Synthesis of the 1-Bromotricyclo[4.1.0.02,7]heptane Adduct with 2-Bromoethanesulfonyl Bromide and Its Transformations

S. G. Kostryukov et al.

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Applied

An Easy, General and Practical Method for the Construction of Alkyl Sulfonyl Fluorides

Xu Zhang et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

Article Chemistry, Organic

Protocol for Stereoselective Construction of Highly Functionalized Dienyl Sulfonyl Fluoride Warheads

Zai-Wei Zhang et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Organic

Clickable Transformation of Nitriles (RCN) to Oxazolyl Sulfonyl Fluoride Warheads

Wan-Yin Fang et al.

ORGANIC LETTERS (2020)

Article Biochemistry & Molecular Biology

Hit-to-lead optimization of a benzene sulfonamide series for potential antileishmanial agents

Paul J. Koovits et al.

RSC MEDICINAL CHEMISTRY (2020)

Article Chemistry, Organic

Light-induced [2+2] cycloadditions for the construction of cyclobutane-fused pyridinyl sulfonyl fluorides

Jing Liu et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Iridium-catalyzed C-H amidation of s-tetrazines

Huan Xiong et al.

CHEMICAL COMMUNICATIONS (2020)

Article Chemistry, Multidisciplinary

Dual ligand-promoted palladium-catalyzed nondirected C-H alkenylation of aryl ethers

Biao Yin et al.

CHEMICAL COMMUNICATIONS (2020)

Article Chemistry, Multidisciplinary

A novel sulfonamide derivative as a strong and selective apototic agent against hematological malignancies

Alisson Bigolin et al.

CHEMICAL PAPERS (2020)

Article Chemistry, Organic

2-Azidoethane-1-sulfonylfluoride (ASF): A Versatile Bis-clickable Reagent for SuFEx and CuAAC Click Reactions

Xu Zhang et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Medicinal

Development of Covalent Ligands for G Protein-Coupled Receptors: A Case for the Human Adenosine A3 Receptor

Xue Yang et al.

JOURNAL OF MEDICINAL CHEMISTRY (2019)

Article Chemistry, Organic

Synthesis of β-Arylethenesulfonyl Fluoride via Pd-Catalyzed Nondirected C-H Alkenylation

Xiao-Yue Chen et al.

ORGANIC LETTERS (2019)

Article Chemistry, Multidisciplinary

Biocompatible SuFEx Click Chemistry: Thionyl Tetrafluoride (SOF4)-Derived Connective Hubs for Bioconjugation to DNA and Proteins

Feng Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Applied

Hydrogenation of nitroaromatics to anilines catalyzed by air-stable arene ruthenium (II)-NNN pincer complexes

Jayaraman Pitchaimani et al.

APPLIED ORGANOMETALLIC CHEMISTRY (2019)

Article Chemistry, Multidisciplinary

Late-Stage Direct o-Alkenylation of Phenols by PdII-Catalyzed C-H Functionalization

Yandong Dou et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

Article Chemistry, Organic

Directed ortho -Metalation of Arenesulfonyl Fluorides and Aryl Fluorosulfates

Alicja Talko et al.

SYNTHESIS-STUTTGART (2019)

Article Chemistry, Multidisciplinary

Utilizing Carbonyl Coordination of Native Amides for Palladium-Catalyzed C(sp3)-H Olefination

Hojoon Park et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Organic

Converting (E)-(Hetero)arylethanesulfonyl Fluorides to (Z)-(Hetero)arylethanesulfonyl Fluorides Under Light Irradiation

Yu-Mei Huang et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Medicinal

Discovery of Benzoylsulfonohydrazides as Potent Inhibitors of the Histone Acetyltransferase KAT6A

David J. Leaver et al.

JOURNAL OF MEDICINAL CHEMISTRY (2019)

Article Chemistry, Medicinal

1,3,4-Oxadiazol-2-ylbenzenesulfonamides as privileged structures for the inhibition of monoamine oxidase B

Anton Shetnev et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2019)

Article Chemistry, Organic

Construction of α-(Hetero)aryl Ethenesulfonyl Fluorides for SuFEx Click Chemistry

Jing Leng et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Multidisciplinary

Cyclic Alkenylsulfonyl Fluorides: Palladium-Catalyzed Synthesis and Functionalization of Compact Multifunctional Reagents

Terry Shing-Bong Lou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Selective Late-Stage Sulfonyl Chloride Formation from Sulfonamides Enabled by Pyry-BF4

Alejandro Gomez-Palomino et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Direct Oxidation of Csp3-H bonds using in Situ Generated Trifluoromethylated Dioxirane in Flow

Mathieu Lesieur et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

Article Chemistry, Medicinal

Kinetic Optimization of Lysine-Targeting Covalent Inhibitors of HSP72

Jonathan Pettinger et al.

JOURNAL OF MEDICINAL CHEMISTRY (2019)

Article Chemistry, Multidisciplinary

An in situ combinatorial methodology to synthesize and screen chemical probes

Antonie J. van der Zouwen et al.

CHEMICAL COMMUNICATIONS (2019)

Article Chemistry, Multidisciplinary

Copper-catalyzed radical approach to allenyl iodides

Yulong Song et al.

CHEMICAL COMMUNICATIONS (2019)

Review Chemistry, Multidisciplinary

The growing applications of SuFEx click chemistry

A. S. Barrow et al.

CHEMICAL SOCIETY REVIEWS (2019)

Article Chemistry, Medicinal

Small molecule inhibitors of anthrax edema factor

Guan-Sheng Jiao et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2018)

Article Chemistry, Multidisciplinary

1-Bromoethene-1-sulfonyl fluoride (BESF) is another good connective hub for SuFEx click chemistry

Christopher J. Smedley et al.

CHEMICAL COMMUNICATIONS (2018)

Article Chemistry, Multidisciplinary

Saturated Heterocyclic Aminosulfonyl Fluorides: New Scaffolds for Protecting-Group-Free Synthesis of Sulfonamides

Sergey A. Zhersh et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

Article Chemistry, Medicinal

Rational approach to highly potent and selective apoptosis signal-regulating kinase 1 (ASK1) inhibitors

Frank Lovering et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2018)

Article Chemistry, Organic

[3+2] Cycloaddition of an Azomethyne Ylide and Vinyl Sulfonyl Fluorides ? an Approach to Pyrrolidine-3-sulfonyl Fluorides

Volodymyr L. Mykhalchuk et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2018)

Review Chemistry, Organic

Sulfonyl Fluorides (SFs): More Than Click Reagents?

Praveen K. Chinthakindi et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Biochemical Research Methods

Synthesis, bioconjugation and stability studies of [F-18]ethenesulfonyl fluoride

Bo Zhang et al.

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS (2018)

Article Chemistry, Organic

[2+2]-Photocycloaddition of N-Benzylmaleimide to Alkenes As an Approach to Functional 3-Azabicyclo[3.2.0]heptanes

Yevhen A. Skalenko et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

C(alkenyl)-H Activation via Six-Membered Palladacycles: Catalytic 1,3-Diene Synthesis

Mingyu Liu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Organic

Sulfonamide Synthesis via Calcium Triflimide Activation of Sulfonyl Fluorides

Paramita Mukherjee et al.

ORGANIC LETTERS (2018)

Article Chemistry, Organic

Efficient synthesis of chalcone-4 '-sulfonyl chlorides and fluorides

Dmitrii Semenok et al.

TETRAHEDRON LETTERS (2018)

Article Chemistry, Organic

Hetaryl Bromides Bearing the SO2F Group - Versatile Substrates for Palladium-Catalyzed C-C Coupling Reactions

Artem Yu. Cherepakha et al.

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ISRAEL JOURNAL OF CHEMISTRY (2017)

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ORGANIC LETTERS (2017)

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CHEMISTRYSELECT (2017)

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

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BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2017)

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BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2016)

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Development of indole sulfonamides as cannabinoid receptor negative allosteric modulators

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BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2016)

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CHINESE JOURNAL OF ORGANIC CHEMISTRY (2016)

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MOLECULES (2016)

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ACS CHEMICAL BIOLOGY (2015)

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CHEMISTRY-A EUROPEAN JOURNAL (2015)

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ACS MEDICINAL CHEMISTRY LETTERS (2015)

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CHEMISTRY-A EUROPEAN JOURNAL (2014)

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Synthesis of 5-(ethylsulfonyl)-2-methoxyaniline: An important pharmacological fragment of VEGFR2 and other inhibitors

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BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2013)

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EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2013)

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Aromatic Sulfonyl Fluorides Covalently Kinetically Stabilize Transthyretin to Prevent Amyloidogenesis while Affording a Fluorescent Conjugate

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

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Synthesis and Evaluation of Activity-Based Probes Carrying a 5′-Fluorosulfonylbenzoyl Adenosine Moiety for Protein Kinases

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JOURNAL OF THE CHINESE CHEMICAL SOCIETY (2013)

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Synthetic Routes of Sulfonamide Derivatives: A Brief Review

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MINI-REVIEWS IN ORGANIC CHEMISTRY (2013)

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Chemoselective synthesis of aryl carboxamido sulfonic acid derivatives

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TETRAHEDRON (2013)

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BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2012)

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Design, synthesis and biological evaluation of β-carboline derivatives as novel inhibitors targeting B-Raf kinase

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BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2012)

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Design and synthesis of procollagen C-proteinase inhibitors

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BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2012)

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The palladium-catalyzed desulfitative cyanation of arenesulfonyl chlorides and sodium sulfinates

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CHEMISTRY-A EUROPEAN JOURNAL (2012)

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Synthesis and biochemical evaluation of triazole/tetrazole-containing sulfonamides against thrombin and related serine proteases

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BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2011)

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Palladium-catalyzed desulfitative C-arylation of a benzo[d]oxazole C-H bond with arene sulfonyl chlorides

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CHEMICAL COMMUNICATIONS (2011)

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EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2011)

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JOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY (2011)

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A convenient synthetic route to 2,4,6-tris(chlorosulfonyl)- and 2,4,6-tris(fluorosulfonyl)phenol, aniline and chlorobenzene

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JOURNAL OF FLUORINE CHEMISTRY (2011)

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Syntheses of a Perfluoroethanesulfonyl Fluoride Vinyl Ether

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Regioselective C-H Activation of Cyclometalated Bis-Tridentate Ruthenium Complexes

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SCIENCE CHINA-CHEMISTRY (2011)

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BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2010)

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CHEMICAL COMMUNICATIONS (2010)

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EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2010)

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Reactions of imines with 2,2-difluoro-2-fluorosulfonylacetyl fluoride

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JOURNAL OF FLUORINE CHEMISTRY (2010)

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The Electrical Properties of Biphenylenes

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ORGANIC LETTERS (2010)

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Synthesis of isomeric fluoronitrobenzene-sulfonyl chlorides

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TETRAHEDRON (2010)

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AUSTRALIAN JOURNAL OF CHEMISTRY (2009)

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JOURNAL OF THE CHINESE CHEMICAL SOCIETY (2009)

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1-Arylsulfonyl-2-(Pyridylmethylsulfinyl) Benzimidazoles as New Proton Pump Inhibitor Prodrugs

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MOLECULES (2009)

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Direct reductive aminations with catalytic molybdenum dioxide dichloride and phenylsilane

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TETRAHEDRON LETTERS (2009)

Article Chemistry, Medicinal

Synthesis and antiproliferative activities of isoindigo and azaisoindigo derivatives

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EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2008)

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Synthesis and biological evaluation of inhibitors of thymidine monophosphate kinase from Bacillus anthracis

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NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS (2008)

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JOURNAL OF MEDICINAL CHEMISTRY (2007)

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C-8 Modifications of 3-alkyl-1,8-dibenzylxanthines as inhibitors of human cytosolic phosphoenolpyruvate carboxykinase

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BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2007)

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From selective substrate analogue factor Xa inhibitors to dual inhibitors of thrombin and factor Xa.: Part 3

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BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2007)

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Azithromycin-sulfonamide conjugates as inhibitors of resistant Streptococcus pyogenes strains

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EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2007)

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Discovery and optimization of a novel series of liver X receptor-α agonists

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BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2006)

Article Chemistry, Organic

A novel synthesis of 2-chloro-4-fluoro-5-nitrobenzenesulfonyl chloride

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ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL (2005)

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Conformationally constrained N1-arylsulfonyltryptamine derivatives as 5-HT6 receptor antagonists

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BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2005)

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JOURNAL OF ORGANIC CHEMISTRY (2005)

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Synthesis and antimicrobial activity of some 2(1H)-quinoxalinone-6-sulfonyl derivatives

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PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS (2005)

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Discovery and evaluation of 2-anilino-5-aryloxazoles as a novel class of VEGFR2 kinase inhibitors

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JOURNAL OF MEDICINAL CHEMISTRY (2005)

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Novel sulfonamide derivatives as inhibitors of histone deacetylase

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HELVETICA CHIMICA ACTA (2005)

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JOURNAL OF FLUORINE CHEMISTRY (2004)

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BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2004)

Article Biochemistry & Molecular Biology

5 '-O-fluorosulfonylbenzoyl esters of purine nucleosides as potential inhibitors of NTPase/helicase and polymerase of Flaviviridae viruses

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NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS (2003)

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CHEMICAL COMMUNICATIONS (2002)

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MAGNETIC RESONANCE IN CHEMISTRY (2001)

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Concise formation of 4-benzyl piperidines and related derivatives using a Suzuki protocol

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JOURNAL OF ORGANIC CHEMISTRY (2001)

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Ion conduction in zwitterionic-type molten salts and their polymers

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JOURNAL OF MATERIALS CHEMISTRY (2001)

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Anilides of (R)-trifluoro-2-hydroxy-2-methylpropionic acid as inhibitors of pyruvate dehydrogenase kinase

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Carbonic anhydrase inhibitors: Inhibition of isozymes I, II and IV by sulfamide and sulfamic acid derivatives

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JOURNAL OF ENZYME INHIBITION (2000)

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Affinity labelling at the 4-hydroxyl group of N-acetylglucosamine and N-acetylgalactosamine

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AUSTRALIAN JOURNAL OF CHEMISTRY (2000)