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  1. Article ; Online: Four-Selective Pyridine Alkylation via Wittig Olefination of Dearomatized Pyridylphosphonium Ylides.

    Fricke, Patrick J / Dolewski, Ryan D / McNally, Andrew

    Angewandte Chemie (International ed. in English)

    2021  Volume 60, Issue 39, Page(s) 21283–21288

    Abstract: Methods to synthesize alkylated pyridines are valuable because these structures are prevalent in pharmaceuticals and agrochemicals. We have developed a distinct approach to construct 4-alkylpyridines using dearomatized pyridylphosphonium ylide ... ...

    Abstract Methods to synthesize alkylated pyridines are valuable because these structures are prevalent in pharmaceuticals and agrochemicals. We have developed a distinct approach to construct 4-alkylpyridines using dearomatized pyridylphosphonium ylide intermediates in a Wittig olefination-rearomatization sequence. Pyridine N-activation is key to this strategy, and N-triazinylpyridinium salts enable coupling between a wide variety of substituted pyridines and aldehydes. The alkylation protocol is viable for late-stage functionalization, including methylation of pyridine-containing drugs. This approach represents an alternative to metal-catalyzed sp
    Language English
    Publishing date 2021-08-23
    Publishing country Germany
    Document type Journal Article ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, Non-P.H.S.
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202109271
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Site-Selective Switching Strategies to Functionalize Polyazines.

    Dolewski, Ryan D / Fricke, Patrick J / McNally, Andrew

    Journal of the American Chemical Society

    2018  Volume 140, Issue 25, Page(s) 8020–8026

    Abstract: Many drug fragments and therapeutic compounds contain multiple pyridines and diazines. Developing site-selective reactions where specific C-H bonds can be transformed in polyazine structures would enable rapid access to valuable derivatives. We present a ...

    Abstract Many drug fragments and therapeutic compounds contain multiple pyridines and diazines. Developing site-selective reactions where specific C-H bonds can be transformed in polyazine structures would enable rapid access to valuable derivatives. We present a study that addresses this challenge by selectively installing a phosphonium ion as a versatile functional handle. Inherent factors that control site-selectivity are described along with mechanistically driven approaches for site-selective switching, where the C-
    MeSH term(s) Acylation ; Carbon/chemistry ; Hydrogen/chemistry ; Ligands ; Organophosphorus Compounds/chemical synthesis ; Organophosphorus Compounds/chemistry ; Pharmaceutical Preparations/chemical synthesis ; Pharmaceutical Preparations/chemistry ; Phosphines/chemical synthesis ; Phosphines/chemistry ; Pyridines/chemical synthesis ; Pyridines/chemistry
    Chemical Substances Ligands ; Organophosphorus Compounds ; Pharmaceutical Preparations ; Phosphines ; Pyridines ; Carbon (7440-44-0) ; Hydrogen (7YNJ3PO35Z)
    Language English
    Publishing date 2018-05-24
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.8b04530
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Bonn / Germany

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  3. Article: Site-Selective Switching Strategies to Functionalize Polyazines

    Dolewski, Ryan D / Fricke, Patrick J / McNally, Andrew

    Journal of the American Chemical Society. 2018 May 24, v. 140, no. 25

    2018  

    Abstract: Many drug fragments and therapeutic compounds contain multiple pyridines and diazines. Developing site-selective reactions where specific C–H bonds can be transformed in polyazine structures would enable rapid access to valuable derivatives. We present a ...

    Abstract Many drug fragments and therapeutic compounds contain multiple pyridines and diazines. Developing site-selective reactions where specific C–H bonds can be transformed in polyazine structures would enable rapid access to valuable derivatives. We present a study that addresses this challenge by selectively installing a phosphonium ion as a versatile functional handle. Inherent factors that control site-selectivity are described along with mechanistically driven approaches for site-selective switching, where the C–+PPh3 group can be predictably installed at other positions in the polyazine system. Simple protocols, readily available reagents, and application to complex drug-like molecules make this approach appealing to medicinal chemists.
    Keywords chemical bonding ; drugs ; pyridines ; therapeutics
    Language English
    Dates of publication 2018-0524
    Size p. 8020-8026.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.8b04530
    Database NAL-Catalogue (AGRICOLA)

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    In stock of ZB MED Bonn / Germany

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  4. Article: Copper-catalyzed hydroamination of propargyl imidates

    Fricke, Patrick J / Alexander C. Gardner / Dylan T. Robbins / Jacqueline Stash / Jenna L. Stasko / Mark J. Ferraro / Michael W. Fennie

    Tetrahedron letters. 2017 Nov. 29, v. 58, no. 48

    2017  

    Abstract: Propargyl imidates derived from aromatic and aliphatic nitriles cyclize at room temperature in high yields when treated with a catalytic amount of copper (I) iodide. This 5-exo-dig process affords dihydrooxazoles which do not aromatize under the reaction ...

    Abstract Propargyl imidates derived from aromatic and aliphatic nitriles cyclize at room temperature in high yields when treated with a catalytic amount of copper (I) iodide. This 5-exo-dig process affords dihydrooxazoles which do not aromatize under the reaction conditions, and which are isolated without chromatography. Investigations of the reaction scope, subsequent functionalization of the reaction products, and preliminary mechanistic data are presented.
    Keywords ambient temperature ; chemical reactions ; chemical structure ; chromatography ; copper ; imidoesters ; iodides ; nitriles
    Language English
    Dates of publication 2017-1129
    Size p. 4510-4513.
    Publishing place Elsevier Ltd
    Document type Article
    ZDB-ID 204287-3
    ISSN 1873-3581 ; 0040-4039
    ISSN (online) 1873-3581
    ISSN 0040-4039
    DOI 10.1016/j.tetlet.2017.10.043
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    In stock of ZB MED Cologne/Königswinter

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  5. Article ; Online: Discovery, Optimization, and Biological Evaluation of Arylpyridones as Cbl-b Inhibitors.

    Mfuh, Adelphe M / Boerth, Jeffrey A / Bommakanti, Gayathri / Chan, Christina / Chinn, Alex J / Code, Erin / Fricke, Patrick J / Giblin, Kathryn A / Gohlke, Andrea / Hansel, Catherine / Hariparsad, Niresh / Hughes, Samantha J / Jin, Meizhong / Kantae, Vasudev / Kavanagh, Stefan L / Lamb, Michelle L / Lane, Jordan / Moore, Rachel / Puri, Taranee /
    Quinn, Taylor R / Reddy, Iswarya / Robb, Graeme R / Robbins, Kevin J / Gancedo Rodrigo, Miguel / Schimpl, Marianne / Singh, Baljinder / Singh, Meha / Tang, Haoran / Thomson, Clare / Walsh, Jarrod J / Ware, Jamie / Watson, Iain D G / Ye, Min-Wei / Wrigley, Gail L / Zhang, Andrew X / Zhang, Yun / Grimster, Neil P

    Journal of medicinal chemistry

    2024  Volume 67, Issue 2, Page(s) 1500–1512

    Abstract: Casitas B-lymphoma proto-oncogene-b (Cbl-b), a member of the Cbl family of RING finger E3 ubiquitin ligases, has been demonstrated to play a central role in regulating effector T-cell function. Multiple studies using gene-targeting approaches have ... ...

    Abstract Casitas B-lymphoma proto-oncogene-b (Cbl-b), a member of the Cbl family of RING finger E3 ubiquitin ligases, has been demonstrated to play a central role in regulating effector T-cell function. Multiple studies using gene-targeting approaches have provided direct evidence that Cbl-b negatively regulates T, B, and NK cell activation via a ubiquitin-mediated protein modulation. Thus, inhibition of Cbl-b ligase activity can lead to immune activation and has therapeutic potential in immuno-oncology. Herein, we describe the discovery and optimization of an arylpyridone series as Cbl-b inhibitors by structure-based drug discovery to afford compound
    MeSH term(s) Proto-Oncogene Proteins c-cbl/metabolism ; Ubiquitin-Protein Ligases/metabolism ; T-Lymphocytes/metabolism ; Phosphorylation ; Ubiquitin/metabolism
    Chemical Substances Proto-Oncogene Proteins c-cbl (EC 2.3.2.27) ; Ubiquitin-Protein Ligases (EC 2.3.2.27) ; Ubiquitin
    Language English
    Publishing date 2024-01-16
    Publishing country United States
    Document type Journal Article
    ZDB-ID 218133-2
    ISSN 1520-4804 ; 0022-2623
    ISSN (online) 1520-4804
    ISSN 0022-2623
    DOI 10.1021/acs.jmedchem.3c02083
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.B 151: Show issues Location:
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