Yevhen Karpun

@zsmu.edu.ua

Department of Natural Sciences for Foreign Students and Toxicological Chemistry/ toxchem.zp.ua
Zaporizhzhia State Medical University

Yevhen Karpun


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https://researchid.co/ekarpun

RESEARCH, TEACHING, or OTHER INTERESTS

Pharmacology (medical), Biochemistry, Organic Chemistry, Biochemistry (medical)
15

Scopus Publications

Scopus Publications

  • Photo and mechanochemically induced reduction of nitroarenes using ammonia borane
    Satenik Mkrtchyan, Vishal B. Purohit, Oleksandr Shalimov, Yevhen Karpun, Ronak V. Prajapati, Vaibhav D. Prajapati, Björn Bielec, Gabriela Addová, Juraj Filo, Pengyue Jin, Cui Wang, Dmitry Katayev, Viktor O. Iaroshenko
    Organic Chemistry Frontiers, 2026
    This study presents an advanced approach for the reduction of nitroarenes to anilines, employing cucurbit[7]uril as a catalyst and ammonia borane as a hydrogen source, signifying noteworthy progression in photochemical supramolecular catalysis.
  • Practical One-Pot Four-Step Synthesis of Isocoumarin-3-Carboxylic Acids
    Roman Y. Vasylyshyn, Bohdan A. Demydchuk, Sergiy M. Kovalenko, Vasyl S. Matiychuk, Svetlana Shishkina, Oleg Lukin, Yevhen Karpun, Alexander Shivanyuk, Volodymyr M. Fetyukhin
    Synlett, 2026
    We report a facile and versatile, one-pot four-step synthesis of functionalized isocoumarin-3-carboxylic acids on a 70–100 g scale. Commercially available substituted anthranilic acids are converted into the corresponding 2-carboxydiazonium bromides, which subsequently undergo the CuBr-catalyzed Meerwein reaction with methyl-2-fluoroacrylate to afford 2-(2-bromo-2-fluoro-3-methoxy-3-oxopropyl)benzoic acids, whereas o-bromobenzoic acids are formed as minor impurities in the concomitant Sandmeyer reactions. The treatment of the reaction mixture with CH2Cl2 and aqueous NaHCO3 removes the salts of the o-bromobenzoic acids into the aqueous phase while 2-(2-bromo-2-fluoro-3-methoxy-3-oxopropyl)benzoic acids cyclize to give methyl 3-fluoro-isocoumarin-3-carboxylates whose trituration with AcOH/HCl/H3BO3 eliminates HF and hydrolyses the ester groups to afford substituted isocoumarin-3-carboxylic acids in overall 42–53% yield.
  • Mechanochemical Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling of Phenol-Derived Cyanate Esters
    Satenik Mkrtchyan, Jiří Zapletal, Yevhen Karpun, Oleksandr Shalimov, Vishal B. Purohit, Vitaliy Yepishev, Gabriela Addová, Juraj Filo, Yuriy Karpenko, Volodymyr Parchenko, Andrii Kaplaushenko, Roman Shcherbyna, Viktor O. Iaroshenko
    European Journal of Organic Chemistry, 2025
    A mechanochemical strategy has been developed for the nickel‐catalyzed Suzuki–Miyaura cross‐coupling of cyano esters derived from phenols, as electrophilic substrates using arylboronic acids via C sp 2 O bond cleavage. This approach capitalizes on the abundance of phenols, using cyano‐functionalized derivatives to enable high reactivity and functional group compatibility without halogenated reagents. The reaction is carried out under solvent‐free, temperature‐trace conditions, significantly reducing environmental impact. The methodology offers a sustainable and scalable alternative for biaryl synthesis, with implications for pharmaceutical and material sciences.
  • The mechanochemical production of biphenyls from nitrogen-containing organic compounds: amides, anilines, and sulfonamides
    Satenik Mkrtchyan, Oleksandr Shalimov, Michael G. Garcia, Sehrish Sarfaraz, Khurshid Ayub, Spartak Khutsishvili, Gabriela Addová, Juraj Filo, Mohanad Shkoor, Vishal B. Purohit, Yevhen Karpun, Vitaliy Yepishev, Jiří Zapletal, Elena Kupcová, Barbora Benická, Viktor O. Iaroshenko
    Organic Chemistry Frontiers, 2025
    The presence of C(sp2)–NH2 in pharmaceutical compounds provokes a demand for the development of techniques for the deaminative functionalization of the C(sp2)–NH2 moiety to enable new routes for the functionalization of complex molecules.
  • Ru-Catalyzed Mechanochemical Trifluoromethylation of Arylboronic Acids and Phenols by in Situ-Generated N-Trifluoromethylpyridinium Salt as CF3 Source
    Satenik Mkrtchyan, Jiří Zapletal, Manoj K. Saini, Eugene Karpun, Vishal B. Purohit, Oleksandr Shalimov, Vitaliy Yepishev, Viktor O. Iaroshenko
    Chemistry A European Journal, 2025
    We report a mechanochemical approach for the ruthenium catalyzed trifluoromethylation of arylboronic acids and phenols under the synergy of trifluoromethylacetamide and pyrylium tetrafluoroborate (Pyry‐BF₄). This is the first ever report on trifluoromethylation using in situ generated N‐trifluoromethylpyridinium tetrafluoroborate as the CF3 source under ball‐milling conditions. The present one‐pot transformation enabled direct trifluoromethylation of arylboronic acids and phenols to deliver the respective trifluoromethyl arenes and aryl trifluoromethyl ethers. It has also shown a remarkable compatibility toward aroyltrifluoroborates for the mechanochemical synthesis of aryl trifluoromethyl ketones. This method offers several advantages, including operational simplicity and broad substrate compatibility. Moreover, the current mechanochemical approach not only proceeds under sustainable conditions but also provides a practical route for the late‐stage modifications of related substrates to access the valuable fluorinated compounds.
  • Ru-Catalyzed Deoxygenative Functionalization of Phenols via π-Coordination Activation: Mechanochemical Access to N-Aryl Amides and α-Aryl Carbonyls
    Satenik Mkrtchyan, Vishal B. Purohit, Yevhen Karpun, Vaibhav D. Prajapati, Ronak V. Prajapati, Vitaliy Yepishev, Oleksandr Shalimov, Gabriela Addová, Juraj Filo, Viktor O. Iaroshenko
    Chemistry A European Journal, 2025
    Given the vast occurrence and availability of both primary amides and phenols, the synthesis of N‐aryl amides via direct coupling between these starting materials would be much attractive. Herein, we report an efficient method for the mechanochemical synthesis of N‐aryl amides via ruthenium‐catalyzed direct amidation of unprotected phenols with primary amides with water as the sole byproduct. Unexpectedly, replacing amides with methyl carboxylic acids, esters, or ketones, the same reaction led to the formation of α‐aryl carbonyl derivatives instead of the anticipated aryl carboxylates. The synthetic strategy accepts a wide scope of primary amides, alkyl carbonyls, and phenolic substrates to deliver 28 expected N‐aryl amides and 14 unexpected α‐aryl carbonyl derivatives with good to excellent yields. The developed synthetic approach would serve as the better alternative to the classical cross‐coupling reactions in context to the PASE (pot, atom, and step economy) synthesis and late‐stage modification of structurally complex molecules, including natural products and pharmaceuticals.
  • Mechanochemical Sequential Deoxygenative Cross-Coupling Reactions of Phenols Under Ruthenium-Nickel Catalysis
    Satenik Mkrtchyan, Vishal B. Purohit, Michał Jakubczyk, Vaibhav D. Prajapati, Ronak V. Prajapati, Michael G. Garcia, Eugene Karpun, Vitaliy Yepishev, Manoj K. Saini, Sehrish Sarfaraz, Khurshid Ayub, Gabriela Addová, Juraj Filo, Viktor O. Iaroshenko
    Molecules, 2025
    Herein, we report the first mechanochemical strategy for the Ru-catalyzed deoxygenative borylation of free phenols via C–O bond cleavage. This Ru-catalyzed phenolic borylation approach has been successfully extended to the Suzuki–Miyaura-type cross-coupling of phenols with aryl bromides. The protocol accepts a wide scope of phenolic substrates, allowing the synthesis of aryl pinacolboranes and biphenyl structures in excellent yields and serving as a better alternative to classical cross-coupling reactions in the context of pot, atom, and step economy synthesis.
  • Mechanochemical decarbonylative transformation of the amide group into OCF3 and CF3 functionalities under ruthenium catalysis
    Satenik Mkrtchyan, Vishal B. Purohit, Oleksandr Shalimov, Michał Jakubczyk, Vaibhav D. Prajapati, Ronak V. Prajapati, Jiří Zapletal, Yevhen Karpun, Vitaliy Yepishev, Gabriela Addová, Juraj Filo, Elena Kupcová, Barbora Benická, Jarmila Kmeťová, Viktor O. Iaroshenko
    Organic Chemistry Frontiers, 2024
    A novel strategy has been developed for the selective transformation of amide groups to CF3 or OCF3 functionalities.
  • German Chamomile (Matricaria chamomilla L.) Flower Extract, Its Amino Acid Preparations and 3D-Printed Dosage Forms: Phytochemical, Pharmacological, Technological, and Molecular Docking Study
    Oleh Koshovyi, Janne Sepp, Valdas Jakštas, Vaidotas Žvikas, Igor Kireyev, Yevhen Karpun, Vira Odyntsova, Jyrki Heinämäki, Ain Raal
    International Journal of Molecular Sciences, 2024
    German chamomile (Matricaria chamomilla L.) is an essential oil- containing medicinal plant used worldwide. The aim of this study was to gain knowledge of the phytochemical composition and the analgesic and soporific activity of Matricaria chamomilla L. (German chamomile) flower extract and its amino acid preparations, to predict the mechanisms of their effects by molecular docking and to develop aqueous printing gels and novel 3D-printed oral dosage forms for the flower extracts. In total, 22 polyphenolic compounds and 14 amino acids were identified and quantified in the M. chamomilla extracts. In vivo animal studies with rodents showed that the oral administration of such extracts revealed the potential for treating of sleep disorders and diseases accompanied by pain. Amino acids were found to potentiate these effects. Glycine enhanced the analgesic activity the most, while lysine and β-alanine improved the soporific activity. The molecular docking analysis revealed a high probability of γ-aminobutyric acid type A (GABAA) and N-methyl-D-aspartate (NMDA) receptor antagonism and 5-lipoxygenase (LOX-5) inhibition by the extracts. A polyethylene oxide (PEO)-based gel composition with the M. chamomilla extracts was proposed for preparing a novel 3D-printed dosage form for oral administration. These 3D-printed extract preparations can be used, for example, in dietary supplement applications.
  • An in silico investigation of 1,2,4-triazole derivatives as potential antioxidant agents using molecular docking, MD simulations, MM-PBSA free energy calculations and ADME predictions
    Yevhen Karpun, Sergiy Fedotov, Anastasiia Khilkovets, Yuriy Karpenko, Volodymyr Parchenko, Yana Klochkova, Yuliia Bila, Iryna Lukina, Natalia Nahorna, Volodymyr Nahornyi
    Pharmacia, 2023
    In this study, we’ve performed computable studies of previously synthesized 1,2,4-triazole derivatives by virtual screening due to antioxidant activity. Six enzymes responsible for regulating oxidative stress were selected as key targets. One hundred and twelve compounds were subjected to semi-flexible molecular docking, which resulted in the selection of 23 substances based on binding energy for further ADME analysis. In addition, molecular dynamics studies of complexes with the best docking scores, reference complexes and apo-proteins were described in detail here. The results of 100 ns modeling (RMSD, RMSF, SASA, Rg, PCA) indicate great stability during the formation of complexes with our two potential compounds, as well as favorable binding energy, which was determined theoretically by means of the MM/PBSA method, thereby increase the likelihood of their acting as promising inhibitors of selected enzymes.
  • Chromato-mass-spectrometric research in salvia grandiflora l., salvia pratensis l. and salvia verticillata l. aboveground organs
    Mykhailo Myha, Oleh Koshovyi, Yevhen Karpun, Alla Kovaleva, Olga Mala, Volodymyr Parchenko, Oleksandr Panasenko, Vera Bunyatyan, Sergiy Kovalenko
    Sciencerise Pharmaceutical Science, 2021
  • Method for trifuzol-neo assay determination by gc-ms
    A.A. Yaroshenko, V.V. Parchenko, O.A. Bihdan, O.I. Panasenko, Yu V. Karpenko, E.O. Karpun
    Research Journal of Pharmacy and Technology, 2021
  • Synthesis, Structure and Properties of Novel S-Substituted BIS-1,2,4-Triazoles
    Yevhen KARPUN
    Hacettepe University Journal of the Faculty of Pharmacy, 2021
  • Synthesis and antimicrobial activity of S-substituted derivatives of 1,2,4-triazol-3-thiol
    Yevhen Karpun, Nataliia Polishchuk
    Sciencerise Pharmaceutical Science, 2021
  • The investigation of antimicrobial activity of some s-substituted bis-1,2l4-triazole-3-thiones
    Yevhen Karpun, Volodymyr Parchenko, Tetiana Fotina, Denys Demianenko, Anatolii Fotin, Volodymyr Nahornyi, Natalia Nahorna
    Pharmacia, 2021