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  1. Article ; Online: (Diazomethyl)dimethylphosphine Oxide - A Diazoalkane Reagent for [3+2] Cycloadditions.

    Slobodyanyuk, Evgeniy Y / Tarasiuk, Ilona / Pasichnyk, Taras / Volochnyuk, Dmitriy M / Sibgatulin, Dmytro O / Grygorenko, Oleksandr O

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2024  Volume 30, Issue 23, Page(s) e202303972

    Abstract: A safe and efficient method for the in-situ preparation of (diazomethyl)dimethylphosphine oxide - a hereto unexplored diazoalkane reagent - is developed. The method is based on the diazotization of the corresponding P(O) ... ...

    Abstract A safe and efficient method for the in-situ preparation of (diazomethyl)dimethylphosphine oxide - a hereto unexplored diazoalkane reagent - is developed. The method is based on the diazotization of the corresponding P(O)Me
    Language English
    Publishing date 2024-03-08
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202303972
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  2. Article ; Online: Stirring-Free Scalable Electrosynthesis Enabled by Alternating Current.

    Bortnikov, Evgeniy O / Smith, Barbara S / Volochnyuk, Dmitriy M / Semenov, Sergey N

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2023  Volume 29, Issue 18, Page(s) e202203825

    Abstract: Alternating current (AC) electrolysis is receiving increased interest as a versatile tool for mild and selective electrochemical transformations. This work demonstrates that AC can enable the concept of a stirring-free electrochemical reactor where the ... ...

    Abstract Alternating current (AC) electrolysis is receiving increased interest as a versatile tool for mild and selective electrochemical transformations. This work demonstrates that AC can enable the concept of a stirring-free electrochemical reactor where the periodic switch of electrode polarity, inherent to AC, provides uniform electrolysis across the whole volume of the reactor. Such design implies a straightforward approach for scaling up electrosynthesis. This was demonstrated on the range of electrochemical transformations performed in three different RVC-packed reactors on up to a 50-mmol scale. Redox-neutral, oxidative, and reductive processes were successfully implemented using the suggested design and the applicable frequency ranges were further investigated for different types of reactions. The advantages of the AC-enabled design - such as the absence of stirring and a maximized surface area of the electrodes - provide the possibility for its universal application both for small-scale screening experimentation and large-scale preparative electrosynthesis without significant optimization needed in between.
    Language English
    Publishing date 2023-02-24
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202203825
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  3. Article ; Online: Saturated Boronic Acids, Boronates, and Trifluoroborates: An Update on Their Synthetic and Medicinal Chemistry.

    Volochnyuk, Dmitriy M / Gorlova, Alina O / Grygorenko, Oleksandr O

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2021  Volume 27, Issue 62, Page(s) 15276

    Abstract: Invited for the cover of this issue are Oleksandr Grygorenko and co-workers at Enamine Ltd., Institute of Organic Chemistry NAS Ukraine, and Taras Shevchenko National University of Kyiv. The image depicts a musical allegory for chemical synthesis: a ... ...

    Abstract Invited for the cover of this issue are Oleksandr Grygorenko and co-workers at Enamine Ltd., Institute of Organic Chemistry NAS Ukraine, and Taras Shevchenko National University of Kyiv. The image depicts a musical allegory for chemical synthesis: a guitar player in a flask, creating notes that become an orgoboron compound. Read the full text of the article at 10.1002/chem.202102108.
    MeSH term(s) Boronic Acids ; Chemistry, Organic ; Chemistry, Pharmaceutical ; Humans
    Chemical Substances Boronic Acids
    Language English
    Publishing date 2021-10-28
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202103751
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  4. Article ; Online: Saturated Boronic Acids, Boronates, and Trifluoroborates: An Update on Their Synthetic and Medicinal Chemistry.

    Volochnyuk, Dmitriy M / Gorlova, Alina O / Grygorenko, Oleksandr O

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2021  Volume 27, Issue 62, Page(s) 15277–15326

    Abstract: This review discusses recent advances in the chemistry of saturated boronic acids, boronates, and trifluoroborates. Applications of the title compounds in the design of boron-containing drugs are surveyed, with special emphasis on α-amino boronic ... ...

    Abstract This review discusses recent advances in the chemistry of saturated boronic acids, boronates, and trifluoroborates. Applications of the title compounds in the design of boron-containing drugs are surveyed, with special emphasis on α-amino boronic derivatives. A general overview of saturated boronic compounds as modern tools to construct C(sp
    MeSH term(s) Alkenes ; Boron ; Boron Compounds ; Boronic Acids ; Chemistry, Pharmaceutical
    Chemical Substances Alkenes ; Boron Compounds ; Boronic Acids ; Boron (N9E3X5056Q)
    Language English
    Publishing date 2021-10-13
    Publishing country Germany
    Document type Journal Article ; Review
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202102108
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  5. Article ; Online: Exploration of the Chemical Space of DNA-encoded Libraries.

    Pikalyova, Regina / Zabolotna, Yuliana / Volochnyuk, Dmitriy M / Horvath, Dragos / Marcou, Gilles / Varnek, Alexandre

    Molecular informatics

    2022  Volume 41, Issue 6, Page(s) e2100289

    Abstract: DNA-Encoded Library (DEL) technology has emerged as an alternative method for bioactive molecules discovery in medicinal chemistry. It enables the simple synthesis and screening of compound libraries of enormous size. Even though it gains more and more ... ...

    Abstract DNA-Encoded Library (DEL) technology has emerged as an alternative method for bioactive molecules discovery in medicinal chemistry. It enables the simple synthesis and screening of compound libraries of enormous size. Even though it gains more and more popularity each day, there are almost no reports of chemoinformatics analysis of DEL chemical space. Therefore, in this project, we aimed to generate and analyze the ultra-large chemical space of DEL. Around 2500 DELs were designed using commercially available building blocks resulting in 2,5B DEL compounds that were compared to biologically relevant compounds from ChEMBL using Generative Topographic Mapping. This allowed to choose several optimal DELs covering the chemical space of ChEMBL to the highest extent and thus containing the maximum possible percentage of biologically relevant chemotypes. Different combinations of DELs were also analyzed to identify a set of mutually complementary libraries allowing to attain even higher coverage of ChEMBL than it is possible with one single DEL.
    MeSH term(s) Cheminformatics ; Chemistry, Pharmaceutical ; DNA/chemistry ; Drug Discovery/methods ; Small Molecule Libraries/chemistry
    Chemical Substances Small Molecule Libraries ; DNA (9007-49-2)
    Language English
    Publishing date 2022-01-28
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2537668-8
    ISSN 1868-1751 ; 1868-1743
    ISSN (online) 1868-1751
    ISSN 1868-1743
    DOI 10.1002/minf.202100289
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  6. Article ; Online: Trifluoromethyl Vinamidinium Salt as a Promising Precursor for Fused β-Trifluoromethyl Pyridines.

    Mityuk, Andrii P / Kiriakov, Oleksandr M / Tiutiunnyk, Vladislav V / Lebed, Pavlo S / Grabchuk, Galyna P / Rusanov, Eduard B / Volochnyuk, Dmitriy M / Ryabukhin, Sergey V

    The Journal of organic chemistry

    2023  Volume 88, Issue 5, Page(s) 2961–2972

    Abstract: An efficient chlorotrimethylsilane-promoted synthetic protocol for the preparation of functionalized fused β-trifluoromethyl pyridines by cyclization of electron-rich aminoheterocycles or substituted anilines with a trifluoromethyl vinamidinium salt was ... ...

    Abstract An efficient chlorotrimethylsilane-promoted synthetic protocol for the preparation of functionalized fused β-trifluoromethyl pyridines by cyclization of electron-rich aminoheterocycles or substituted anilines with a trifluoromethyl vinamidinium salt was developed. The efficient and scalable approach for producing represented trifluoromethyl vinamidinium salt demonstrated huge prospects for further use. The structure specificities of the trifluoromethyl vinamidinium salt and their impact on the reaction progress were determined. The procedure's scope and alternative ways of the reaction were investigated. The possibility of increasing the reaction scale up to 50 g and further modification of obtained products was shown. A minilibrary of potential fragments for
    Language English
    Publishing date 2023-02-16
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.2c02684
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    In stock of ZB MED Cologne/Königswinter

    Zs.A 4473: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (2.OG)
    ab Jg. 2022: Lesesaal (EG)

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  7. Article ; Online: Expanding the Chemical Space of 1,2-Difunctionalized Cyclobutanes.

    Chernykh, Anton V / Kudryk, Oleksandr V / Olifir, Oleksandr S / Dobrydnev, Alexey V / Rusanov, Eduard / Moskvina, Viktoriia S / Volochnyuk, Dmitriy M / Grygorenko, Oleksandr O

    The Journal of organic chemistry

    2023  Volume 88, Issue 5, Page(s) 3109–3131

    Abstract: An efficient approach to the synthesis of previously unavailable or hardly accessible 1,2-difunctionalized cyclobutanes (mostly with ... ...

    Abstract An efficient approach to the synthesis of previously unavailable or hardly accessible 1,2-difunctionalized cyclobutanes (mostly with NH
    Language English
    Publishing date 2023-02-13
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.2c02892
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    In stock of ZB MED Cologne/Königswinter

    Zs.A 4473: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (2.OG)
    ab Jg. 2022: Lesesaal (EG)

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  8. Article: Multigram Synthesis of 4,4-disubstituted-3-oxopyrrolidones – Efficient Starting Material for Diverse 3 Functionalized Pyrrolidones

    Bondarenko, Semen / Fedorchenko, Anatolii / Novosolov, Pavlo / Marchenko, Oleksandr / Hanopolskyi, Anton / Volovenko, Yulian M. / Volochnyuk, Dmitriy M / Ryabukhin, Serhiy V.

    Synlett

    2024  

    Abstract: The practical rapid development of chemical leads for drug discovery strongly depends on scalable building block synthesis procedures. N-heterocyclic moieties, especially unsaturated ones, remain essential tools in the hands of screening and medicinal ... ...

    Abstract The practical rapid development of chemical leads for drug discovery strongly depends on scalable building block synthesis procedures. N-heterocyclic moieties, especially unsaturated ones, remain essential tools in the hands of screening and medicinal chemists. Here, we report four novel chemical block families and the interconversions between them. 4,4-disubstituted-3-oxopyrrolidones synthesis was an essential milestone in the diversity-oriented production of 3-aminopyrrolidones, 3-hydroxypyrrolidones and 3,3’-difluoropyrrolidines. Those can be functionalized with conformationally flexible spirocyclic substituents. We developed the multigram procedure for 4,4-disubstituted-3-oxopyrrolidones from commercially accessible and cost-saving reagents via the short three-step procedure. Also, here we are reporting the robust conversion procedure of 3-oxopyrrolidones to 3-aminopyrrolidones, 3,3’-difluoropyrrolidones and 3-hydroxypyrrolidones, involving a minimal amount of steps. We demonstrate the scope and limitations and further perspectives for such synthetic approaches.
    Language English
    Publishing date 2024-05-06
    Publisher Georg Thieme Verlag KG
    Publishing place Stuttgart ; New York
    Document type Article
    ZDB-ID 2042012-2
    ISSN 1437-2096 ; 0936-5214
    ISSN (online) 1437-2096
    ISSN 0936-5214
    DOI 10.1055/a-2320-8362
    Database Thieme publisher's database

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  9. Article ; Online: Fluoral Hydrate: A Perspective Substrate for the Castagnoli-Cushman Reaction.

    Adamovskyi, Mykhailo I / Avramenko, Mykola M / Volochnyuk, Dmitriy M / Ryabukhin, Sergey V

    ACS omega

    2020  Volume 5, Issue 33, Page(s) 20932–20942

    Abstract: The reactivity of azomethines based on trifluoroacetaldehyde hydrate in the Castagnoli-Cushman reaction (CCR) was researched. The impact of the nature of anhydrides explored on the reaction route was determined. The preparative procedures for the ... ...

    Abstract The reactivity of azomethines based on trifluoroacetaldehyde hydrate in the Castagnoli-Cushman reaction (CCR) was researched. The impact of the nature of anhydrides explored on the reaction route was determined. The preparative procedures for the synthesis of N-substituted (3
    Language English
    Publishing date 2020-08-17
    Publishing country United States
    Document type Journal Article
    ISSN 2470-1343
    ISSN (online) 2470-1343
    DOI 10.1021/acsomega.0c02394
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  10. Article ; Online: The Symbiotic Relationship Between Drug Discovery and Organic Chemistry.

    Grygorenko, Oleksandr O / Volochnyuk, Dmitriy M / Ryabukhin, Sergey V / Judd, Duncan B

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2019  Volume 26, Issue 6, Page(s) 1196–1237

    Abstract: All pharmaceutical products contain organic molecules; the source may be a natural product or a fully synthetic molecule, or a combination of both. Thus, it follows that organic chemistry underpins both existing and upcoming pharmaceutical products. The ... ...

    Abstract All pharmaceutical products contain organic molecules; the source may be a natural product or a fully synthetic molecule, or a combination of both. Thus, it follows that organic chemistry underpins both existing and upcoming pharmaceutical products. The reverse relationship has also affected organic synthesis, changing its landscape towards increasingly complex targets. This Review article sets out to give a concise appraisal of this symbiotic relationship between organic chemistry and drug discovery, along with a discussion of the design concepts and highlighting key milestones along the journey. In particular, criteria for a high-quality compound library design enabling efficient virtual navigation of chemical space, as well as rise and fall of concepts for its synthetic exploration (such as combinatorial chemistry; diversity-, biology-, lead-, or fragment-oriented syntheses; and DNA-encoded libraries) are critically surveyed.
    MeSH term(s) Bacteria/drug effects ; Biological Products/chemistry ; Biological Products/metabolism ; DNA/chemistry ; Drug Discovery ; Glucose Transport Proteins, Facilitative/antagonists & inhibitors ; Glucose Transport Proteins, Facilitative/metabolism ; High-Throughput Screening Assays ; Organic Chemicals/chemical synthesis ; Organic Chemicals/chemistry ; Organic Chemicals/pharmacology ; Small Molecule Libraries/chemical synthesis ; Small Molecule Libraries/chemistry ; Small Molecule Libraries/pharmacology
    Chemical Substances Biological Products ; Glucose Transport Proteins, Facilitative ; Organic Chemicals ; Small Molecule Libraries ; DNA (9007-49-2)
    Language English
    Publishing date 2019-10-30
    Publishing country Germany
    Document type Journal Article ; Review
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.201903232
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