A5050222498- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Fluorine in Organic Chemistry
- Chemical Synthesis and Analysis
- Cyclopropane Reaction Mechanisms
- Synthesis and Catalytic Reactions
- Synthesis and Biological Evaluation
- Synthesis and Reactions of Organic Compounds
- Crystallography and molecular interactions
- Radical Photochemical Reactions
- Catalytic C–H Functionalization Methods
- Click Chemistry and Applications
- Organic Chemistry Cycloaddition Reactions
- Asymmetric Synthesis and Catalysis
- Carbohydrate Chemistry and Synthesis
- Oxidative Organic Chemistry Reactions
- Chemical Synthesis and Reactions
- Synthesis of β-Lactam Compounds
- Sulfur-Based Synthesis Techniques
- Inorganic Fluorides and Related Compounds
- Antimicrobial Peptides and Activities
- Synthesis and Characterization of Heterocyclic Compounds
- Synthesis of heterocyclic compounds
- Synthesis and biological activity
- Catalytic Cross-Coupling Reactions
Taras Shevchenko National University of Kyiv
2016-2025
Enamine (Ukraine)
2016-2025
Institute of Bioorganic Chemistry and Petrochemistry V.P. Kukhar
2024
Robert Bosch (Germany)
2023
Torrey Pines Institute For Molecular Studies
2019
Scripps (United States)
2019
Scripps Institution of Oceanography
2019
Scripps Research Institute
2019
Division of Chemistry
2017-2019
Laboratoire de Chimie Organique
2016-2017
Historically accessed through two-electron, anionic chemistry, ketones, alcohols, and amines are of foundational importance to the practice organic synthesis. After placing this work in proper historical context, Article reports development, full scope, a mechanistic picture for strikingly different way forging such functional groups. Thus, carboxylic acids, once converted redox-active esters (RAEs), can be utilized as formally nucleophilic coupling partners with other derivatives (to...
Abstract Saturated bioisosteres of ortho ‐disubstituted benzenes (bicyclo[2.1.1]hexanes) were synthesized, characterized and validated. These cores incorporated into the bioactive compounds Valsartan, Boskalid Fluxapyroxad instead benzene ring. The saturated analogues showed a similar level antifungal activity compared to that .
A useful protocol for achieving decarboxylative cross-coupling (DCC) of redox-active esters (RAE, isolated or generated in situ) and halo(hetero)arenes is reported. This pragmatically focused study employs a unique Ag-Ni electrocatalytic platform to overcome numerous limitations that have plagued this strategically powerful transformation. In its optimized form, coupling partners can be combined surprisingly simple way: open the air, using technical-grade solvents, an inexpensive ligand Ni...
Abstract The ortho -substituted phenyl ring is a basic structural element in chemistry. It found more than three hundred drugs and agrochemicals. During the past decade, scientists have tried to replace bioactive compounds with saturated bioisosteres obtain novel patentable structures. However, most of research this area has been devoted replacement para ring. Here we developed improved physicochemical properties: 2-oxabicyclo[2.1.1]hexanes. Crystallographic analysis revealed that these...
After more than 20 years of trials, a practical scalable approach to fluoro-substituted bicyclo[1.1.1]pentanes (F-BCPs) has been developed. The physicochemical properties the F-BCPs have studied, and core was incorporated into structure anti-inflammatory drug Flurbiprofen in place fluorophenyl ring.
Abstract A general approach to 3‐azabicyclo[3.1.1]heptanes by reduction of spirocyclic oxetanyl nitriles was developed. The mechanism, scope, and scalability this transformation were studied. core incorporated into the structure antihistamine drug Rupatidine instead pyridine ring, which led a dramatic improvement in physicochemical properties.
1,2-Disubstituted bicyclo[2.1.1]hexanes have been synthesized, characterized, and biologically validated as saturated bioisosteres of the ortho -substituted benzene ring.
The Pauson-Khand reaction has in the past 50 years become one of most common cycloaddition reactions chemistry. Coupling two unsaturated bonds with carbon monoxide, transformation remains limited to CO as a C
A chemical reagent to access methyl sulfones has been developed. Its reaction with various bis-nucleophiles leads the rapid formation of previously unknown heteroaromatic sulfones. Analogous strategy can also be used construct alkyl-, CHF2-, CF3- and even bicyclo[1.1.1]pentane-containing derivatives. These compounds have demonstrated a high potential for use in medicinal chemistry coordination chemistry. Methyl sulfone is standard polar substituent found different agro chemicals or drugs but...
Abstract Photobiological processes in nature are usually triggered by nonpeptidic chromophores or modified side chains. A system is presented which the polypeptide backbone itself can be conformationally switched light. An amino acid analogue was designed and synthesized based on a reversibly photoisomerizable diarylethene scaffold. This incorporated into cyclic of antimicrobial peptide gramicidin S at several sites. The biological activity resulting peptidomimetics could then effectively...
A novel approach to agrochemically important difluoromethyl-substituted pyrazoles has been developed based on the elusive reagent CF2 HCHN2 , which was synthesized (generated in situ) for first time and employed [3+2] cycloaddition reactions with alkynes. The reaction is extremely practical as it a one-pot process, does not require catalyst or isolation of potentially toxic explosive gaseous intermediate, proceeds common solvent, namely chloroform, air. also scalable allows preparation...
A practical synthetic approach to the difluoro-substituted bicyclo[1.1.1]pentanes was developed. The key step an addition of difluorocarbene (:CF2) electron-rich bicyclo[1.1.0]butanes by CF3TMS/NaI system. obtained difluoro-bicyclo[1.1.1]pentanes are suggested be used as saturated bioisosteres benzene rings for purpose drug discovery projects.
A new generation of saturated benzene mimetics, 2-oxabicyclo[2.1.1]hexanes, was developed. These compounds were designed as analogues bicyclo[1.1.1]pentane with an improved water solubility. Crystallographic analysis 2-oxabicyclo[2.1.1]hexanes revealed that they occupy a novel chemical space, but, at the same time, resemble motif meta-disubstituted benzenes.
Abstract The [3+2] cycloaddition of CF 3 CHN 2 , generated in situ, with electron‐deficient alkenes/alkynes affords ‐substituted pyrazolines/pyrazoles quantitative yields. one‐pot three‐component reaction between CH NH · HCl, NaNO and the substrate proceeds at room temperature dichloromethane/water.
A simple and robust method for electrochemical alkyl C–H fluorination is presented. Using a nitrate additive, widely available fluorine source (Selectfluor), carbon-based electrodes, wide variety of activated unactivated bonds are converted into their C–F congeners. The scalability the reaction also demonstrated with 100 gram preparation fluorovaline.
Abstract This work bridges a gap in the cross‐coupling of aliphatic redox‐active esters with aryl zinc reagents. Previously limited to primary, secondary, and specialized tertiary centers, new protocol has been devised enable coupling general systems using nickel catalysis. The scope this operationally simple method is broad, it can be used simplify synthesis medicinally relevant motifs bearing quaternary centers.
Sulfonylated aromatics are commonplace motifs in drugs and agrochemicals. However, methods for the direct synthesis of sulfonylated non-classical arene bioisosteres, which could improve physicochemical properties drug agrochemical candidates, limited. Here we report a solution to this challenge: one-pot halosulfonylation [1.1.1]propellane, [3.1.1]propellane bicyclo[1.1.0]butanes that proceeds under practical, scalable mild conditions. The sulfonyl halides used chemistry feature aryl,...
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. design structure based on analysis advantages disadvantages previously used bioisosteres: bicyclo[1.1.1]pentane, bicyclo[2.2.2]octane, cubane. key synthesis step iodocyclization cyclohexane-containing alkenyl alcohols molecular iodine acetonitrile. 2-Oxabicyclo[2.2.2]octane core...
Abstract We have developed a general and practical approach towards 2‐oxabicyclo[2.1.1]hexanes with two three exit vectors via an iodocyclization reaction. The obtained compounds been easily converted into the corresponding building blocks for use in medicinal chemistry. 2‐Oxabicyclo[2.1.1]hexanes incorporated structure of five drugs agrochemicals, validated biologically as bioisosteres ortho ‐ meta ‐benzenes.
Abstract There is a pressing need, particularly in the field of drug discovery, for general methods that will enable direct coupling tertiary alkyl fragments to (hetero)aryl halides. Herein uniquely powerful and simple set conditions achieving this transformation with unparalleled generality chemoselectivity disclosed. This new protocol placed context other recently reported methods, applied simplify routes known bioactive building blocks molecules, scaled up both batch flow. The role...