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  1. Article ; Online: The Longer Route can be Better: Electrosynthesis in Extended Path Flow Cells.

    Brown, Richard C D

    Chemical record (New York, N.Y.)

    2021  Volume 21, Issue 9, Page(s) 2472–2487

    Abstract: This personal account provides an overview of work conducted in my research group, and through collaborations with other chemists and engineers, to develop flow electrolysis cells and apply these cells in organic electrosynthesis. First, a brief summary ... ...

    Abstract This personal account provides an overview of work conducted in my research group, and through collaborations with other chemists and engineers, to develop flow electrolysis cells and apply these cells in organic electrosynthesis. First, a brief summary of my training and background in organic synthesis is provided, leading in to the start of flow electrosynthesis in my lab in collaboration with Derek Pletcher. Our work on the development of extended path electrolysis flow reactors is described from a synthetic organic chemist's perspective, including laboratory scale-up to give several moles of an anodic methoxylation product in one day. The importance of cell design is emphasised with regards to achieving good performance in laboratory electrosynthesis with productivities from hundreds of mg h
    Language English
    Publishing date 2021-07-24
    Publishing country United States
    Document type Journal Article ; Review
    ZDB-ID 2044646-9
    ISSN 1528-0691 ; 1527-8999
    ISSN (online) 1528-0691
    ISSN 1527-8999
    DOI 10.1002/tcr.202100163
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: The risk associated with organophosphorus nerve agents: from their discovery to their unavoidable threat, current medical countermeasures and perspectives.

    Voros, Camille / Dias, José / Timperley, Christopher M / Nachon, Florian / Brown, Richard C D / Baati, Rachid

    Chemico-biological interactions

    2024  Volume 395, Page(s) 110973

    Abstract: The first organophosphorus nerve agent was discovered accidently during the development of pesticides, shortly after the first use of chemical weapons (chlorine, phosgene) on the battlefield during World War I. Despite the Chemical Weapons Convention ... ...

    Abstract The first organophosphorus nerve agent was discovered accidently during the development of pesticides, shortly after the first use of chemical weapons (chlorine, phosgene) on the battlefield during World War I. Despite the Chemical Weapons Convention banning these substances, they have still been employed in wars, terrorist attacks or political assassinations. Characterised by their high lethality, they target the nervous system by inhibiting the acetylcholinesterase (AChE) enzyme, preventing neurotransmission, which, if not treated rapidly, inevitably leads to serious injury or the death of the person intoxicated. The limited efficacy of current antidotes, known as AChE reactivators, pushes research towards new treatments. Numerous paths have been explored, from modifying the original pyridinium oximes to developing hybrid reactivators seeking a better affinity for the inhibited AChE. Another crucial approach resides in molecules more prone to cross the blood-brain barrier: uncharged compounds, bio-conjugated reactivators or innovative formulations. Our aim is to raise awareness on the threat and toxicity of organophosphorus nerve agents and to present the main synthetic efforts deployed since the first AChE reactivator, to tackle the task of efficiently treating victims of these chemical warfare agents.
    MeSH term(s) Humans ; Nerve Agents/toxicity ; Organophosphorus Compounds/toxicity ; Animals ; Cholinesterase Reactivators/pharmacology ; Cholinesterase Reactivators/therapeutic use ; Cholinesterase Reactivators/chemistry ; Medical Countermeasures ; Acetylcholinesterase/metabolism ; Cholinesterase Inhibitors/toxicity ; Chemical Warfare Agents/toxicity ; Antidotes/pharmacology ; Antidotes/therapeutic use ; Oximes/pharmacology ; Oximes/therapeutic use ; Oximes/chemistry
    Language English
    Publishing date 2024-04-02
    Publishing country Ireland
    Document type Journal Article ; Review
    ZDB-ID 218799-1
    ISSN 1872-7786 ; 0009-2797
    ISSN (online) 1872-7786
    ISSN 0009-2797
    DOI 10.1016/j.cbi.2024.110973
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Aryl-aryl cross-coupling reactions without reagents or catalysts: photocyclization of

    Sun, Wei / Wilding-Steele, Luke / Brown, Richard C D / Harrowven, David C

    Chemical communications (Cambridge, England)

    2023  Volume 59, Issue 72, Page(s) 10797–10800

    Abstract: Cyclisations of ... ...

    Abstract Cyclisations of benzyl
    Language English
    Publishing date 2023-09-07
    Publishing country England
    Document type Journal Article
    ZDB-ID 1472881-3
    ISSN 1364-548X ; 1359-7345 ; 0009-241X
    ISSN (online) 1364-548X
    ISSN 1359-7345 ; 0009-241X
    DOI 10.1039/d3cc03271j
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article: 1-Butyl-3-methylimidazolium tetrafluoroborate as suitable solvent for BF

    David, Marta / Galli, Elisa / Brown, Richard C D / Feroci, Marta / Vetica, Fabrizio / Bortolami, Martina

    Beilstein journal of organic chemistry

    2023  Volume 19, Page(s) 1966–1981

    Abstract: In order to replace the expensive metal/ligand catalysts and classic toxic and volatile solvents, commonly used for the hydration of alkynes, the hydration reaction of alkynes was studied in the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ( ...

    Abstract In order to replace the expensive metal/ligand catalysts and classic toxic and volatile solvents, commonly used for the hydration of alkynes, the hydration reaction of alkynes was studied in the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate (BMIm-BF
    Language English
    Publishing date 2023-12-28
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2192461-2
    ISSN 1860-5397
    ISSN 1860-5397
    DOI 10.3762/bjoc.19.147
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Molecular mechanisms and evolutionary robustness of a color switch in proteorhodopsins.

    Mao, Jiafei / Jin, Xinsheng / Shi, Man / Heidenreich, David / Brown, Lynda J / Brown, Richard C D / Lelli, Moreno / He, Xiao / Glaubitz, Clemens

    Science advances

    2024  Volume 10, Issue 4, Page(s) eadj0384

    Abstract: Proteorhodopsins are widely distributed photoreceptors from marine bacteria. Their discovery revealed a high degree of evolutionary adaptation to ambient light, resulting in blue- and green-absorbing variants that correlate with a conserved glutamine/ ... ...

    Abstract Proteorhodopsins are widely distributed photoreceptors from marine bacteria. Their discovery revealed a high degree of evolutionary adaptation to ambient light, resulting in blue- and green-absorbing variants that correlate with a conserved glutamine/leucine at position 105. On the basis of an integrated approach combining sensitivity-enhanced solid-state nuclear magnetic resonance (ssNMR) spectroscopy and linear-scaling quantum mechanics/molecular mechanics (QM/MM) methods, this single residue is shown to be responsible for a variety of synergistically coupled structural and electrostatic changes along the retinal polyene chain, ionone ring, and within the binding pocket. They collectively explain the observed color shift. Furthermore, analysis of the differences in chemical shift between nuclei within the same residues in green and blue proteorhodopsins also reveals a correlation with the respective degree of conservation. Our data show that the highly conserved color change mainly affects other highly conserved residues, illustrating a high degree of robustness of the color phenotype to sequence variation.
    MeSH term(s) Biological Evolution ; Cell Nucleus ; Glutamine ; Norisoprenoids ; Rhodopsins, Microbial
    Chemical Substances proteorhodopsin ; Glutamine (0RH81L854J) ; Norisoprenoids ; Rhodopsins, Microbial
    Language English
    Publishing date 2024-01-24
    Publishing country United States
    Document type Journal Article
    ZDB-ID 2810933-8
    ISSN 2375-2548 ; 2375-2548
    ISSN (online) 2375-2548
    ISSN 2375-2548
    DOI 10.1126/sciadv.adj0384
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article ; Online: The synthesis of biologically active indolocarbazole natural products.

    Chambers, George E / Sayan, A Emre / Brown, Richard C D

    Natural product reports

    2021  Volume 38, Issue 10, Page(s) 1794–1820

    Abstract: Covering: up to 2020The indolocarbazoles, in particular indolo[2,3- ...

    Abstract Covering: up to 2020The indolocarbazoles, in particular indolo[2,3-
    MeSH term(s) Biological Products/chemical synthesis ; Biological Products/pharmacology ; Carbazoles/chemical synthesis ; Carbazoles/pharmacology ; Humans ; Indoles/chemical synthesis ; Indoles/pharmacology ; Structure-Activity Relationship
    Chemical Substances Biological Products ; Carbazoles ; Indoles
    Language English
    Publishing date 2021-10-20
    Publishing country England
    Document type Journal Article ; Research Support, Non-U.S. Gov't ; Review
    ZDB-ID 2002546-4
    ISSN 1460-4752 ; 0265-0568
    ISSN (online) 1460-4752
    ISSN 0265-0568
    DOI 10.1039/d0np00096e
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article: First example of organocatalysis by cathodic N-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell.

    Rocco, Daniele / Folgueiras-Amador, Ana A / Brown, Richard C D / Feroci, Marta

    Beilstein journal of organic chemistry

    2022  Volume 18, Page(s) 979–990

    Abstract: In this paper we present the first electrochemical generation of NHC carried out in a divided flow cell. The flow cell operated in the recycle mode. The need for a divided cell derived from the anodic electroactivity of the electrogenerated carbene. In ... ...

    Abstract In this paper we present the first electrochemical generation of NHC carried out in a divided flow cell. The flow cell operated in the recycle mode. The need for a divided cell derived from the anodic electroactivity of the electrogenerated carbene. In order to have NHC accumulation in the catholyte, the Nafion membrane (cell separator) was pretreated with an alkaline solution. The formation of NHC was quantified as its reaction product with elemental sulfur. The NHC was successfully used as organocatalyst in two classical umpolung reactions of cinnamaldehyde: its cyclodimerization and its oxidative esterification.
    Language English
    Publishing date 2022-08-05
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2192461-2
    ISSN 1860-5397
    ISSN 1860-5397
    DOI 10.3762/bjoc.18.98
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  8. Article ; Online: Spatio-temporal detachment of homogeneous electron transfer in controlling selectivity in mediated organic electrosynthesis.

    Hodgson, Jack W / Folgueiras-Amador, Ana A / Pletcher, Derek / Harrowven, David C / Denuault, Guy / Brown, Richard C D

    Faraday discussions

    2023  Volume 247, Page(s) 302–323

    Abstract: In electrosynthesis, electron transfer (ET) mediators are normally chosen such that they are more easily reduced (or oxidised) than the substrate for cathodic (or anodic) processes; setting the electrode potential to the mediator therefore ensures ... ...

    Abstract In electrosynthesis, electron transfer (ET) mediators are normally chosen such that they are more easily reduced (or oxidised) than the substrate for cathodic (or anodic) processes; setting the electrode potential to the mediator therefore ensures selective heterogeneous ET with the mediator at the electrode, rather than the substrate. The current work investigates the opposite, and counter intuitive, situation for a successful mediated electroreductive process where the mediator (phenanthrene) has a reduction potential that is negative to that of the substrate, and the cathode potential is set negative to both (
    Language English
    Publishing date 2023-10-31
    Publishing country England
    Document type Journal Article
    ISSN 1364-5498
    ISSN (online) 1364-5498
    DOI 10.1039/d3fd00089c
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  9. Article ; Online: Photoinduced Formation of Cubyl Aryl Thioethers and Synthesis of Monocubyl Analogue of Dapsone.

    Donnier-Valentin, Laly / Kassamba, Seydou / Legros, Julien / Fressigné, Catherine / Vuluga, Daniela / Brown, Richard C D / Linclau, Bruno / De Paolis, Michaël

    Organic letters

    2023  Volume 25, Issue 48, Page(s) 8580–8584

    Abstract: 1,4-Disubstituted cubyl aryl thioethers were generated from the corresponding iodocubanes and aryl thiolates upon UV irradiation in dimethyl sulfoxide at room temperature. This simple procedure was found to be compatible with a variety of substituted ... ...

    Abstract 1,4-Disubstituted cubyl aryl thioethers were generated from the corresponding iodocubanes and aryl thiolates upon UV irradiation in dimethyl sulfoxide at room temperature. This simple procedure was found to be compatible with a variety of substituted aryl thiolates. This finding paved the way to a synthesis of the monocubyl analogue of dapsone, a key molecule in the treatment of leprosy, also known as Hansen's disease, and of acne.
    Language English
    Publishing date 2023-11-21
    Publishing country United States
    Document type Journal Article
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.3c03372
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  10. Article: The synthesis of biologically active indolocarbazole natural products

    Chambers, George E. / Sayan, A. Emre / Brown, Richard C. D.

    Natural product reports. 2021 Oct. 20, v. 38, no. 10

    2021  

    Abstract: The indolocarbazoles, in particular indolo[2,3-a]pyrrolo[3,4-c]carbazole derivatives, are an important class of natural products that exhibit a wide range of biological activities. There has been a plethora of synthetic approaches to this family of ... ...

    Abstract The indolocarbazoles, in particular indolo[2,3-a]pyrrolo[3,4-c]carbazole derivatives, are an important class of natural products that exhibit a wide range of biological activities. There has been a plethora of synthetic approaches to this family of natural products, leading to advances in chemical methodology, as well as affording access to molecular scaffolds central to protein kinase drug discovery programmes. In this review, we compile and summarise the synthetic approaches to the indolo[2,3-a]pyrrolo[3,4-c]carbazole derivatives, spanning the period from their isolation in 1980 up to 2020. The selected natural products include indolocarbazoles not functionalised at indolic nitrogen, pyranosylated indolocarbazoles, furanosylated indolocarbazoles and disaccharideindolocarbazoles.
    Keywords drugs ; nitrogen ; protein kinases
    Language English
    Dates of publication 2021-1020
    Size p. 1794-1820.
    Publishing place The Royal Society of Chemistry
    Document type Article
    ZDB-ID 2002546-4
    ISSN 1460-4752 ; 0265-0568
    ISSN (online) 1460-4752
    ISSN 0265-0568
    DOI 10.1039/d0np00096e
    Database NAL-Catalogue (AGRICOLA)

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