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  1. Article ; Online: Development of on-DNA Formation of Benzofuran for DNA-Encoded Library Synthesis.

    Luo, Ayun / Zhou, Hongxia / Wang, Xiuming / Zeng, Fanming / Yu, Weina / Yang, Kexin / Duchemin, Nicolas / Hu, Yun Jin

    Organic letters

    2024  Volume 26, Issue 8, Page(s) 1688–1693

    Abstract: Using a novel homologation-heterocyclization cascade, the on-DNA synthesis of benzofurans from aldehydes has been developed. The methodology, based on an innovative use of the Seyferth-Gilbert homologation, followed by a high yielding Sonogashira ... ...

    Abstract Using a novel homologation-heterocyclization cascade, the on-DNA synthesis of benzofurans from aldehydes has been developed. The methodology, based on an innovative use of the Seyferth-Gilbert homologation, followed by a high yielding Sonogashira coupling in situ intramolecular cyclization one-pot, two-step reaction, provides a powerful and unique pathway for DNA-encoded library (DEL) synthesis of a wide array of pharmaceutically relevant benzofuran-based scaffolds.
    MeSH term(s) Benzofurans ; Gene Library ; Cyclization ; DNA
    Chemical Substances benzofuran (LK6946W774) ; Benzofurans ; DNA (9007-49-2)
    Language English
    Publishing date 2024-02-22
    Publishing country United States
    Document type Journal Article
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.4c00187
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article: Development of the Inverse Sonogashira Reaction for DEL Synthesis.

    Luo, Ayun / Zhou, Hongxia / Hua, Qini / An, Yufang / Ma, Hangke / Zhao, Xue / Yang, Kexin / Hu, Yun Jin

    ACS medicinal chemistry letters

    2023  Volume 14, Issue 3, Page(s) 270–277

    Abstract: An efficient approach for aryl acetylene DNA-encoded library (DEL) synthesis was developed in this study by transition-metal-mediated inverse Sonogashira reaction of 1-iodoalkyne with boronic acid under ambient conditions, with moderate to excellent ... ...

    Abstract An efficient approach for aryl acetylene DNA-encoded library (DEL) synthesis was developed in this study by transition-metal-mediated inverse Sonogashira reaction of 1-iodoalkyne with boronic acid under ambient conditions, with moderate to excellent conversions and broad substrate adaptability for the first time. Compared to palladium-phosphine, copper iodide performed better in the on-DNA inverse Sonogashira reaction. Interestingly, substrate diversity can be enhanced by first interrogating coupling reagents under copper-promoted conditions, and then revalidating them under palladium-facilitated conditions for those reagents which failed under the former. This complementary validation strategy is particularly well-fitted to any DEL validation studies.
    Language English
    Publishing date 2023-02-23
    Publishing country United States
    Document type Journal Article
    ISSN 1948-5875
    ISSN 1948-5875
    DOI 10.1021/acsmedchemlett.2c00477
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Development of On-DNA Thiophene Synthesis for DEL Construction.

    Luo, Ayun / Duchemin, Nicolas / Wang, Xiuming / Zhou, Hongxia / Zeng, Fanming / Zhao, Xue / Yu, Weina / Yang, Kexin / Jin Hu, Yun

    Chemistry, an Asian journal

    2023  Volume 18, Issue 15, Page(s) e202300458

    Abstract: Thiophene and its substituted derivatives are a highly important class of heterocyclic compounds, with noteworthy applications in pharmaceutical ingredients. In this study, we leverage the unique reactivity of alkynes to generate thiophenes on-DNA, using ...

    Abstract Thiophene and its substituted derivatives are a highly important class of heterocyclic compounds, with noteworthy applications in pharmaceutical ingredients. In this study, we leverage the unique reactivity of alkynes to generate thiophenes on-DNA, using a cascade iodination, Cadiot-Chodkiewicz coupling and heterocyclization. This approach, tackling on-DNA thiophene synthesis for the first time, generates diverse, and unprecedented structural and chemical features, which could be significant motifs in DEL screening as molecular recognition agents for drug discovery.
    Language English
    Publishing date 2023-06-30
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2233006-9
    ISSN 1861-471X ; 1861-4728
    ISSN (online) 1861-471X
    ISSN 1861-4728
    DOI 10.1002/asia.202300458
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article ; Online: On-DNA Alkyne Iodination and Acetylenic Coupling as a Useful Tool for DEL Synthesis.

    Luo, Ayun / Zhou, Hongxia / Zhou, Qi / Hua, Qini / Zhao, Xue / Yu, Xiaobing / Yang, Kexin / Hu, Yun Jin

    Bioconjugate chemistry

    2022  

    Abstract: 1-Iodoalkynes and 1,3-diynes are versatile chemical intermediates and pharmaceutically valuable ingredients. In this study, copper mediated on-DNA alkyne iodination and Cadiot-Chodkiewicz coupling are developed for the first time. This generates diverse, ...

    Abstract 1-Iodoalkynes and 1,3-diynes are versatile chemical intermediates and pharmaceutically valuable ingredients. In this study, copper mediated on-DNA alkyne iodination and Cadiot-Chodkiewicz coupling are developed for the first time. This generates diverse, systematic, and unprecedented topographic structural features, which could be invaluable as molecular recognition agents for drug discovery in DEL screening.
    Language English
    Publishing date 2022-11-30
    Publishing country United States
    Document type Journal Article
    ZDB-ID 1024041-x
    ISSN 1520-4812 ; 1043-1802
    ISSN (online) 1520-4812
    ISSN 1043-1802
    DOI 10.1021/acs.bioconjchem.2c00471
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

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  5. Article ; Online: Kinugasa Reaction for DNA-Encoded β-Lactam Library Synthesis.

    Luo, Ayun / Zhang, Ziqi / Zeng, Fanming / Wang, Xiuming / Zhao, Xue / Yang, Kexin / Hu, Yun Jin

    Organic letters

    2022  Volume 24, Issue 31, Page(s) 5756–5761

    Abstract: β-Lactam antibiotics are one of the most important antibacterial drug classes worldwide. This work will present the first prototype on-DNA β-lactam combinatorial library with novel structures and chemical space properties that would be significant for ... ...

    Abstract β-Lactam antibiotics are one of the most important antibacterial drug classes worldwide. This work will present the first prototype on-DNA β-lactam combinatorial library with novel structures and chemical space properties that would be significant for phenotypic screening to identify the next generation of antibiotics to combat the pervasive problem of bacterial resistance.
    MeSH term(s) Anti-Bacterial Agents/pharmacology ; DNA ; beta-Lactams/pharmacology
    Chemical Substances Anti-Bacterial Agents ; beta-Lactams ; DNA (9007-49-2)
    Language English
    Publishing date 2022-08-02
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.2c02237
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article: A Neutral Metal-Free System for Head-to-Tail Dimerization of Electron-Rich Alkenes

    Luo, A-Yun / Bao, Yan / Cheng, Xiu-Fen / Wang, Xi-Sheng

    Synthesis

    2017  Volume 49, Issue 17, Page(s) 3962–3967

    Abstract: A neutral metal-free system for the head-to-tail dimerization of electron-rich alkenes with stoichiometric amount of BrCCl 2 H and NaI is reported. This reaction proceeds under mild conditions with high efficiency and broad scope. ...

    Abstract A neutral metal-free system for the head-to-tail dimerization of electron-rich alkenes with stoichiometric amount of BrCCl 2 H and NaI is reported. This reaction proceeds under mild conditions with high efficiency and broad scope.
    Keywords metal-free ; head-to-tail ; dimerization ; electron-rich alkenes ; BrCCl ; H
    Language English
    Publishing date 2017-06-20
    Publisher © Georg Thieme Verlag
    Publishing place Stuttgart ; New York
    Document type Article
    ZDB-ID 2033062-5
    ISSN 1437-210X ; 0039-7881
    ISSN (online) 1437-210X
    ISSN 0039-7881
    DOI 10.1055/s-0036-1589039
    Database Thieme publisher's database

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