3‐Trifluoromethylated Coumarins and Carbostyrils by Radical Trifluoromethylation of <i>ortho</i>‐Functionalized Cinnamic Esters

Chaabouni, Slim; Simonet, Florent; François, Achille; Abid, Souhir; Galaup, Chantal; Chassaing, Stefan

doi:10.1002/ejoc.201601181

Cited by 16 publications

(3 citation statements)

References 70 publications

(16 reference statements)

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“…High temperature and low radical yield limit their application, however. Alternatively, Togni’s and Umemoto’s reagents are better choices, and they require activation by various transition metals (e.g., Ru(bipyridine) 3 Cl 2 , and CuI). The increased efficiency of generation and the reactivity of the radical depend largely on the metal-containing compounds that are used.…”

Section: Fast Labeling Reagents: Reactive Radical Speciesmentioning

confidence: 99%

Mass Spectrometry-Based Protein Footprinting for Higher-Order Structure Analysis: Fundamentals and Applications

2020

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Proteins adopt different higher-order structures (HOS) to enable their unique biological functions. Understanding the complexities of protein higher-order structures and dynamics requires integrated approaches, where mass spectrometry (MS) is now positioned to play a key role. One of those approaches is protein footprinting. Although the initial demonstration of footprinting was for the HOS determination of protein/nucleic acid binding, the concept was later adapted to MS-based protein HOS analysis, through which different covalent labeling approaches “mark” the solvent accessible surface area (SASA) of proteins to reflect protein HOS. Hydrogen–deuterium exchange (HDX), where deuterium in D2O replaces hydrogen of the backbone amides, is the most common example of footprinting. Its advantage is that the footprint reflects SASA and hydrogen bonding, whereas one drawback is the labeling is reversible. Another example of footprinting is slow irreversible labeling of functional groups on amino acid side chains by targeted reagents with high specificity, probing structural changes at selected sites. A third footprinting approach is by reactions with fast, irreversible labeling species that are highly reactive and footprint broadly several amino acid residue side chains on the time scale of submilliseconds. All of these covalent labeling approaches combine to constitute a problem-solving toolbox that enables mass spectrometry as a valuable tool for HOS elucidation. As there has been a growing need for MS-based protein footprinting in both academia and industry owing to its high throughput capability, prompt availability, and high spatial resolution, we present a summary of the history, descriptions, principles, mechanisms, and applications of these covalent labeling approaches. Moreover, their applications are highlighted according to the biological questions they can answer. This review is intended as a tutorial for MS-based protein HOS elucidation and as a reference for investigators seeking a MS-based tool to address structural questions in protein science.

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Section: Fast Labeling Reagents: Reactive Radical Speciesmentioning

confidence: 99%

Mass Spectrometry-Based Protein Footprinting for Higher-Order Structure Analysis: Fundamentals and Applications

2020

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“…The reaction was accomplished in high yields with the Togni reagent as the CF 3 source, by using copper(l) iodide as catalyst in DMF, under microwave irradiation at 80 °C for 7 h, and under inert atmosphere [ 78 ].…”

Section: Synthetic Strategies For the Preparation Of Coumarinsmentioning

confidence: 99%

Coumarin: A Natural, Privileged and Versatile Scaffold for Bioactive Compounds

et al. 2018

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Many naturally occurring substances, traditionally used in popular medicines around the world, contain the coumarin moiety. Coumarin represents a privileged scaffold for medicinal chemists, because of its peculiar physicochemical features, and the versatile and easy synthetic transformation into a large variety of functionalized coumarins. As a consequence, a huge number of coumarin derivatives have been designed, synthesized, and tested to address many pharmacological targets in a selective way, e.g., selective enzyme inhibitors, and more recently, a number of selected targets (multitarget ligands) involved in multifactorial diseases, such as Alzheimer’s and Parkinson’s diseases. In this review an overview of the most recent synthetic pathways leading to mono- and polyfunctionalized coumarins will be presented, along with the main biological pathways of their biosynthesis and metabolic transformations. The many existing and recent reviews in the field prompted us to make some drastic selections, and therefore, the review is focused on monoamine oxidase, cholinesterase, and aromatase inhibitors, and on multitarget coumarins acting on selected targets of neurodegenerative diseases.

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“…In addition, fluorine is the most electronegative of all elements, which endows it with unique properties. Indeed, it is commonly accepted that introducing a fluorine-containing group onto the molecule scaffold often leads to improvement of the molecular chemical, physical, and biological properties [ 42 ]. To date, the trifluoromethyl (CF 3 ) group has appeared as the archetypal and most sought-after fluorine-containing group, and there have been reported a huge and ever-increasing number of trifluoromethylated compounds in the literature [ 43 , 44 ].…”

Section: Introductionmentioning

confidence: 99%

Novel Trifluoromethylcoumarinyl Urea Derivatives: Synthesis, Characterization, Fluorescence, and Bioactivity

Qiao

Hao

2018

Molecules

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A series of novel trifluoromethylcoumarinyl urea derivatives were designed, synthesized, and characterized by 1H-NMR, 13C-NMR, and HR-ESI-MS. The fluorescence spectra of the target compounds were recorded. The spectra show that most of the title compounds glow green with λmaxem of 500–517 nm, while compounds 5r, 5s, 5u, and 5l (compounds named by authors) glow violet with λmaxem of 381–443 nm. Moreover, the herbicidal and antifungal activities of the synthesized compounds were evaluated for their potential use as pesticides. The results indicate that compound 5f against the caulis of Amaranthus retroflexus and compounds 5j and 5l against the taproot of Digitaria sanguinalis are equivalent to the commercial herbicide Acetochlor. Nine of the title compounds are more antifungal than commercial fungicide Carbendazim against Botrytis cinerea.

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3‐Trifluoromethylated Coumarins and Carbostyrils by Radical Trifluoromethylation of ortho‐Functionalized Cinnamic Esters

Cited by 16 publications

References 70 publications

Mass Spectrometry-Based Protein Footprinting for Higher-Order Structure Analysis: Fundamentals and Applications

Mass Spectrometry-Based Protein Footprinting for Higher-Order Structure Analysis: Fundamentals and Applications

Coumarin: A Natural, Privileged and Versatile Scaffold for Bioactive Compounds

Novel Trifluoromethylcoumarinyl Urea Derivatives: Synthesis, Characterization, Fluorescence, and Bioactivity

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