Oxidation with a “Stopover” – Stable Zwitterions as Intermediates in the Oxidation of α‐Tocopherol (Vitamin E) Model Compounds to their Corresponding ortho‐Quinone Methides
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DOI: 10.1002/open.202000306
Abstract: Abstract As a prominent member of the vitamin E group, α‐tocopherol is an important lipophilic antioxidant. It has a special oxidation chemistry that involves phenoxyl radicals, quinones and quinone methides. During the oxidation to the… read more here.
Keywords: quinone methide; oxidation; quinone methides; rotation ... See more keywords
1,6-Conjugate addition of C-nucleophiles to p-quinone methide surrogate: Synthesis of diarylpropanes
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DOI: 10.1016/j.tet.2018.12.048
Abstract: Abstract 1,6-Conjugate addition of various carbon nucleophiles to p-quinone methide surrogate is reported. The active methylene containing C-nucleophiles such as 1,3-diketones, diesters and ketoesters underwent two consecutive additions leading to bis-addition products, diarylpropanes. Whereas, nitroalkanes… read more here.
Keywords: conjugate addition; nucleophiles quinone; synthesis; addition ... See more keywords
o-Quinone methide with overcrowded olefinic core as a catalytically-active surrogate of triarylmethylium salt for dehydridative oxidation of benzylic alcohols under aerobic photoirradiation conditions
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DOI: 10.1016/j.tet.2021.132459
Abstract: Abstract An o-quinone methide (o-QM) competent as a catalyst for the dehydridative oxidation of benzylic alcohols was developed. The introduction of an overcrowded olefinic component into the o-QM induced structural distortion, beneficial for imparting triarylmethylium… read more here.
Keywords: quinone methide; dehydridative oxidation; oxidation benzylic; benzylic alcohols ... See more keywords
PNA Conjugates of Quinone Methide Precursors Alkylate RNA after Activation with Light.
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DOI: 10.1021/acs.bioconjchem.9b00796
Abstract: Quinone methide precursors 2 and 3 were protected with a photoreactive 2-nitrobenzyl group and conjugated to peptide nucleic acids (PNA) using a Huisgen click reaction. After brief irradiation at 365 nm, crosslinking with com-plementary RNA… read more here.
Keywords: quinone methide; alkylate rna; methide precursors; precursors alkylate ... See more keywords
Metabolic Activation of Militarine In Vitro and In Vivo.
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DOI: 10.1021/acs.chemrestox.1c00430
Abstract: Bletilla striata is consumed as food and herbal medicine. Militarine (MLT) is a major ingredient in B. striata. Previous studies demonstrated that MLT showed teratogenic toxicity to zebrafish embryos. The present study aimed to identify… read more here.
Keywords: activation militarine; metabolic activation; militarine; quinone methide ... See more keywords
Nonenzymatic Self-Assembly Access to Diverse ortho-Quinone Methide-Based Pseudonatural Products.
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DOI: 10.1021/acs.orglett.2c02268
Abstract: A nonenzymatic self-assembly program was introduced to explore diverse clavatol-based pseudonatural products (PNPs) in a marine-derived fungus. Intermolecular couplings of the chemoreactive ortho-quinone methide of clavatol with native acceptors led to 14 clavatol-based PNPs with… read more here.
Keywords: nonenzymatic self; based pseudonatural; self assembly; pseudonatural products ... See more keywords
Photogeneration of quinone methide from adamantylphenol in an ultrafast non-adiabatic dehydration reaction
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DOI: 10.1039/d1cp05690e
Abstract: The ultrafast photochemical reaction of quinone methide (QM) formation from adamantylphenol was monitored in real time using femtosecond transient absorption spectroscopy and fluorescence upconversion in solution at room temperature. Experiments were complemented by theoretical studies… read more here.
Keywords: reaction; photogeneration quinone; non adiabatic; quinone methide ... See more keywords
Stereoselective Reactions of ortho-Quinone Methide and ortho-Quinone Methide Imines and Their Utility in Natural Product Synthesis
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DOI: 10.1055/s-0037-1610241
Abstract: Herein presented is a review of the reactivity and synthetic utility of ortho-quinone methides and ortho-quinone methide imines. These versatile intermediates have received significant attention in the literature and new methods for their preparation and… read more here.
Keywords: quinone methide; ortho quinone; utility; methide imines ... See more keywords
Recent Advances in Quinone Methide Chemistry for Protein-Proximity Capturing
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DOI: 10.1055/s-0042-1751402
Abstract: Here we summarize the most recent findings in the chemical-, photo-, or enzyme-triggered generation of nitrogen and oxygen anions leading to the formation of quinone methide intermediates (QMIs). This short review is divided into two… read more here.
Keywords: chemistry; advances quinone; generation nitrogen; quinone methide ... See more keywords
Synthesis, Isolation and Biological Evaluation of a New Active Quinone Methide Derived Curcuminoid
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DOI: 10.31254/phyto.2021.10110
Abstract: A new curcuminoid, quinone methide cyclopentadione (QMC), was synthesized by oxidation of curcumin (CUR) in the presence of potassium ferricyanide, and further isolated and analyzed. QMC was found to be a relatively water-soluble curcuminoid, and… read more here.
Keywords: cur; methide derived; qmc; quinone methide ... See more keywords
Antimalarial and antitumour activities of the steroidal quinone-methide celastrol and its combinations with artemiside, artemisone and methylene blue
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DOI: 10.3389/fphar.2022.988748
Abstract: Artemisinin, isolated from the traditional Chinese medicinal plant qīng hāo 青蒿 (Artemisia annua) and its derivatives are used for treatment of malaria. With treatment failures now being recorded for the derivatives and companion drugs used… read more here.
Keywords: artemiside artemisone; methide celastrol; amino artemisinins; quinone methide ... See more keywords