Quinone methide
View article: Synthesis and Trapping of the Elusive Ortho-Iminoquinone Methide Derived from α-Tocopheramine and Comparison to the Case of α-Tocopherol
Synthesis and Trapping of the Elusive Ortho-Iminoquinone Methide Derived from α-Tocopheramine and Comparison to the Case of α-Tocopherol Open
Tocopheramines are a class of antioxidants which are distinguished from tocopherols (vitamin E) by the presence of an amino group instead of the phenolic hydroxyl group. α-Tocopheramine is intensively studied for biomedical applications bu…
View article: A Palladium-Catalyzed Cascade Double Annulation Strategy for Modular Access to Dihydrocyclopenta[<i>b</i>]chromenes
A Palladium-Catalyzed Cascade Double Annulation Strategy for Modular Access to Dihydrocyclopenta[<i>b</i>]chromenes Open
The cyclopentachromene skeleton is a key structural motif in pharmaceutical and fluorescent materials. We here introduce a Pd-promoted double ring-closure strategy for tackling the modular synthesis of densely functionalized dihydrocyclope…
View article: Development of a novel family of antifungal agents based on a quinone methide oxime framework
Development of a novel family of antifungal agents based on a quinone methide oxime framework Open
View article: A hydrophobic photouncaging reaction to profile the lipid droplet interactome in tissues
A hydrophobic photouncaging reaction to profile the lipid droplet interactome in tissues Open
Most bioorthogonal photouncaging reactions preferentially occur in polar environments to accommodate biological applications in the aqueous cellular milieu. However, they are not precisely designed to chemically adapt to the diverse microe…
View article: Stimuli‐Responsive Prodrug Linkers That Simultaneously Release Cargo and Neutralize In Situ Generated (Aza)Quinone Methides
Stimuli‐Responsive Prodrug Linkers That Simultaneously Release Cargo and Neutralize In Situ Generated (Aza)Quinone Methides Open
Self‐immolative linkers that use p ‐amino/hydroxy‐benzyloxycarbonyl (PABC/PHBC) spacers are essential to the mechanism of many prodrugs. However, a highly reactive (aza)quinone methide is generated as a potential toxic byproduct. To remove…
View article: Synthesis of Unsymmetrical Z‐Azo‐Arenes: Base‐Mediated 1,6‐Conjugate Addition of Arylhydrazine to <i>para</i>‐Quinone Methide
Synthesis of Unsymmetrical Z‐Azo‐Arenes: Base‐Mediated 1,6‐Conjugate Addition of Arylhydrazine to <i>para</i>‐Quinone Methide Open
A simple and straightforward method has been developed for the direct synthesis of unsymmetrical Z‐azo‐aryl compounds from p‐quinone methide ( p ‐QM) and arylhydrazine. This reaction strategy is executed in air under basic conditions and a…
View article: Synthesis of 2‐(1<i>H</i>‐Azol‐1‐ylmethyl)phenols from <i>ortho</i>‐Quinone Methide Precursors and NH‐Azoles under Solvent‐ and Catalyst‐Free Conditions
Synthesis of 2‐(1<i>H</i>‐Azol‐1‐ylmethyl)phenols from <i>ortho</i>‐Quinone Methide Precursors and NH‐Azoles under Solvent‐ and Catalyst‐Free Conditions Open
We have developed a non‐catalytic method for the ortho ‐hydroxybenzylation of NH‐azoles that differ significantly in nucleophilicity and basicity (imidazoles, benzimidazoles, pyrazoles and others) with ortho ‐quinone methide precursors (sa…
View article: Facile synthesis of recyclable polythioimidocarbonates <i>via</i> aromatization-driven alternating copolymerization of <i>para</i> -quinone methide and isothiocyanates
Facile synthesis of recyclable polythioimidocarbonates <i>via</i> aromatization-driven alternating copolymerization of <i>para</i> -quinone methide and isothiocyanates Open
For the first time, the aromatization-driven alternating copolymerization of p -QM with isothiocyanates is explored under mild conditions.
View article: Synthesis of fused-ring systems and diarylmethane flavonoids <i>via ortho</i>-quinone methide intermediates
Synthesis of fused-ring systems and diarylmethane flavonoids <i>via ortho</i>-quinone methide intermediates Open
Facile syntheses of a series of novel fused-ring flavanone systems via Mannich reactions and o -QM cycloadditions and evaluation of their anticancer effects.
View article: Anti-inflammatory effects of para-quinone methide derivatives on ulcerative colitis
Anti-inflammatory effects of para-quinone methide derivatives on ulcerative colitis Open
A series of para -quinone methide derivatives were evaluated their anti-inflammatory activity. Through the screening of the lipopolysaccharide (LPS)-induced inflammatory cell model in Raw264.7 cells, it was found that the inhibitory activi…
View article: Front Cover Picture: Gold‐Catalyzed Synthesis of <i>Ortho</i>‐Quinone Methide Analogues as Reactive Synthetic Precursors (Adv. Synth. Catal. 10/2024)
Front Cover Picture: Gold‐Catalyzed Synthesis of <i>Ortho</i>‐Quinone Methide Analogues as Reactive Synthetic Precursors (Adv. Synth. Catal. 10/2024) Open
The front cover illustrates pandas as gold catalysts on trees, with the leaves symbolizing reaction reagents, intermediates, and products. It portrays the 5-exo-dig-selective cyclization of α,β-ynones. The smiling panda under the tree capt…
View article: Catalytic pyrolysis mechanism of lignin moieties driven by aldehyde, hydroxyl, methoxy, and allyl functionalization: the role of reactive quinone methide and ketene intermediates
Catalytic pyrolysis mechanism of lignin moieties driven by aldehyde, hydroxyl, methoxy, and allyl functionalization: the role of reactive quinone methide and ketene intermediates Open
The complex catalytic pyrolysis mechanism of key lignin monomers demonstrates how functional groups dictate product pathways, revealing insights to enhance desired chemical yields and minimize catalyst deactivation.
View article: <i>Ortho</i>-quinone methide driven synthesis of kynurenic acid lactams
<i>Ortho</i>-quinone methide driven synthesis of kynurenic acid lactams Open
Lactam formation of different KYNA amides and Mannich bases mediated by ortho -quinone methide has been investigated.
View article: Superoxide-responsive quinone methide precursors (QMP-SOs) to study superoxide biology by proximity labeling and chemoproteomics
Superoxide-responsive quinone methide precursors (QMP-SOs) to study superoxide biology by proximity labeling and chemoproteomics Open
QMP-SOs are molecular probes capable of proximity labeling of proteins in a superoxide-dependent manner. This enables fluorescence imaging of superoxide and profiling proteins associated with superoxide biology by chemoproteomics.
View article: A novel bioresponsive self-immolative spacer based on aza-quinone methide reactivity for the controlled release of thiols, phenols, amines, sulfonamides or amides
A novel bioresponsive self-immolative spacer based on aza-quinone methide reactivity for the controlled release of thiols, phenols, amines, sulfonamides or amides Open
The power of pyrrole: a 1,6-self-immolative spacer designed on the pyrrole structure enables direct late-stage functionalisation of drugs and their traceless release under enzymatic or reductive micellar catalysis in water.
View article: Antioxidant Activity and Skin Sensitization of Eugenol and Isoeugenol: Two Sides of the Same Coin?
Antioxidant Activity and Skin Sensitization of Eugenol and Isoeugenol: Two Sides of the Same Coin? Open
Eugenol and isoeugenol are well acknowledged to possess antioxidant and thus cytoprotective activities. Yet both compounds are also important skin sensitizers, compelling the cosmetics and fragrance industries to notify their presence in m…
View article: Catecholamine Derivatives as Novel Crosslinkers for the Synthesis of Versatile Biopolymers
Catecholamine Derivatives as Novel Crosslinkers for the Synthesis of Versatile Biopolymers Open
Catecholamine metabolites are not only involved in primary metabolism, but also in secondary metabolism, serving a diverse array of physiologically and biochemically important functions. Melanin, which originates from dopa and dopamine, fo…
View article: Leveraging the Persistent Radical Effect in the Synthesis of <i>trans</i> ‐2,3‐Diaryl Dihydrobenzofurans**
Leveraging the Persistent Radical Effect in the Synthesis of <i>trans</i> ‐2,3‐Diaryl Dihydrobenzofurans** Open
A simple method for accessing trans‐ 2,3‐diaryl dihydrobenzofurans is reported. This approach leverages the equilibrium between quinone methide dimers and their persistent radicals. This equilibrium is disrupted by phenols that yield compa…
View article: Maytenus octogona Superoxide Scavenging and Anti-Inflammatory Caspase-1 Inhibition Study Using Cyclic Voltammetry and Computational Docking Techniques
Maytenus octogona Superoxide Scavenging and Anti-Inflammatory Caspase-1 Inhibition Study Using Cyclic Voltammetry and Computational Docking Techniques Open
The relationship between oxidative stress and inflammation is well known, and exogenous antioxidants, primarily phytochemical natural products, may assist the body’s endogenous defense systems in preventing diseases due to excessive inflam…
View article: Synthesis of Functionalized Tetrahydroquinoline Containing Indole Scaffold via Chemoselective Annulation of Aza-<i>ortho</i>-quinone Methide Precursor
Synthesis of Functionalized Tetrahydroquinoline Containing Indole Scaffold via Chemoselective Annulation of Aza-<i>ortho</i>-quinone Methide Precursor Open
The chemoselective annulation of aza-ortho-quinone methide generated by in situ o-chloromethyl sulfonamide has been achieved with bifunctional acyclic olefin. This efficient approach provides access to the diastereoselective …
View article: Synthesis and Photochemical Properties of Fluorescent Metabolites Generated from Fluorinated Benzoylmenadiones in Living Cells
Synthesis and Photochemical Properties of Fluorescent Metabolites Generated from Fluorinated Benzoylmenadiones in Living Cells Open
This work describes the reactivity and properties of fluorinated derivatives (F-PD and F-PDO) of plasmodione (PD) and its metabolite, the plasmodione oxide (PDO). Introduction of a fluorine atom on the 2-methyl …
View article: Rational design of flavoprotein oxidases for biocatalytic valorization of lignin-derived monomers
Rational design of flavoprotein oxidases for biocatalytic valorization of lignin-derived monomers Open
Biocatalytic valorization of lignin-derived phenolic compounds has emerged as a promising biorefinery strategy in the challenging production of value-added fine chemicals. VAO(vanillyl alcohol oxidase)-type oxidases are promising biocataly…
View article: Leveraging the persistent radical effect in the synthesis of trans-2,3-diaryl-dihydrobenzofurans
Leveraging the persistent radical effect in the synthesis of trans-2,3-diaryl-dihydrobenzofurans Open
A simple method for accessing trans-2,3-diaryl-dihydrobenzofurans is reported. This approach leverages a persistent radical equilibrium between quinone methide dimers and the persistent phenoxyl radicals derived therefrom. This equilibrium…
View article: Bioorthogonal photocatalytic quinone methide decaging for cell-cell interaction labeling
Bioorthogonal photocatalytic quinone methide decaging for cell-cell interaction labeling Open
Cell-cell interactions (CCIs) play crucial roles in directing diverse biological processes in multicellular organisms, making the high-sensitivity and selectivity characterization of the diverse CCIs in high demand yet still challenging. W…
View article: Self-Immobilizing Quinone Methides for the Fluorescent Sensing of Enzyme Activity
Self-Immobilizing Quinone Methides for the Fluorescent Sensing of Enzyme Activity Open
Gaining insight into biological processes relies on sensitive analytical techniques. These often require labeling of biomolecules that help visualize them. Selective covalent labeling without preliminary modification of the biomolecules is…
View article: Mechanism of action of an Ir(<scp>iii</scp>) complex bearing a boronic acid active as a H<sub>2</sub>O<sub>2</sub>-responsive photosensitizer: ROS generation and quinone methide release for GSH scavenging
Mechanism of action of an Ir(<span>iii</span>) complex bearing a boronic acid active as a H<sub>2</sub>O<sub>2</sub>-responsive photosensitizer: ROS generation and quinone methide release for GSH scavenging Open
The mechanism of action by computational exploration of an Ir( iii ) complex bearing an aryl boronic acid moiety aiming at detecting H 2 O 2 in cancer cells to generate an Ir( iii )-based phototosensitizer and quinone methide able to scave…
View article: Synthesis and Biological Characterisation of a New Prodrug Based on Aza-Quinone Methide Reactivity for the Release of a Thiol-Containing Hdac Inhibitor
Synthesis and Biological Characterisation of a New Prodrug Based on Aza-Quinone Methide Reactivity for the Release of a Thiol-Containing Hdac Inhibitor Open
View article: Leveraging the persistent radical effect in the synthesis of trans-2,3-diaryl-dihydrobenzofurans
Leveraging the persistent radical effect in the synthesis of trans-2,3-diaryl-dihydrobenzofurans Open
A simple method for accessing trans-2,3-diaryl-dihydrobenzofurans is reported. This approach leverages a persistent radical equilibrium between quinone methide dimers and the persistent phenoxyl radicals derived therefrom. This equilibrium…
View article: Photoactivatable V‐Shaped Bifunctional Quinone Methide Precursors as a New Class of Selective G‐quadruplex Alkylating Agents
Photoactivatable V‐Shaped Bifunctional Quinone Methide Precursors as a New Class of Selective G‐quadruplex Alkylating Agents Open
Combining the selectivity of G‐quadruplex (G4) ligands with the spatial and temporal control of photochemistry is an emerging strategy to elucidate the biological relevance of these structures. In this work, we developed six novel V‐shaped…
View article: Organocatalytic atroposelective construction of axially chiral N, N- and N, S-1,2-azoles through novel ring formation approach
Organocatalytic atroposelective construction of axially chiral N, N- and N, S-1,2-azoles through novel ring formation approach Open