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| http://dx.doi.org/10.1021/cr100003s | DOI Listing |
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Copper-Catalyzed [2,3]-Sigmatropic Rearrangement of Azide-Ynamides via Selenium Ylides.
Org Lett
January 2025
Yunnan Key Laboratory of Modern Separation Analysis and Substance Transformation, College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, China.
A copper-catalyzed [2,3]-sigmatropic rearrangement of azide-ynamides via selenium ylides is disclosed, which leads to the practical and divergent synthesis of a variety of tricyclic heterocycles bearing a quaternary carbon stereocenter in generally moderate to excellent yields. Significantly, this method represents the first [2,3]-sigmatropic rearrangement of the selenium ylide based on alkynes and an unprecedented [2,3]-sigmatropic rearrangement via α-imino copper carbenes.
View Article and Find Full Text PDFNovel Covalent Probe Selectively Targeting Glutathione Peroxidase 4 In Vivo: Potential Applications in Pancreatic Cancer Therapy.
J Med Chem
February 2024
State Key Laboratory of Bioactive Molecules and Druggability Assessment, Jinan University, 601 Huangpu Avenue West, Guangzhou 510632, China.
Glutathione peroxidase 4 (GPX4) emerges as a promising target for the treatment of therapy-resistant cancer through ferroptosis. Thus, there is a broad interest in the development of GPX4 inhibitors. However, a majority of reported GPX4 inhibitors utilize chloroacetamide as a reactive electrophilic warhead, and the selectivity and pharmacokinetic properties still need to be improved.
View Article and Find Full Text PDFYnamide Coupling Reagent for the Chemical Cross-Linking of Proteins in Live Cells.
ACS Chem Biol
June 2023
International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development (MOE), MOE Key Laboratory of Tumor Molecular Biology, School of Pharmacy, Jinan University, 601 Huangpu Avenue West, Guangzhou 510632, China.
Chemical cross-linking of proteins coupled with mass spectrometry analysis (CXMS) is a powerful method for the study of protein structure and protein-protein interactions (PPIs). However, the chemical probes used in the CXMS are limited to bidentate reactive warheads, and the available zero-length cross-linkers are restricted to 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride/-hydroxysuccinimide (EDC/NHS) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM). To alleviate this issue, an efficient coupling reagent, sulfonyl ynamide, was developed as a new zero-length cross-linker that can connect high-abundance carboxyl residues (D/E) with lysine (K) to form amide bonds in the absence of any catalyst.
View Article and Find Full Text PDFRegio- and stereospecific -hydrophenoxylation of ynamides with acidic phenols.
Org Biomol Chem
April 2023
Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology, the NMPA and State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences and the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, Guangdong 511436, P. R. China.
Herein we describe a self-acid-enabled chemo-, regio-, and stereospecific -hydrophenoxylation of ynamides under reagent-free conditions. The presence of a non-polar solvent such as toluene was found to be beneficial to facilitate the rate-limiting proton transfer between phenols and ynamides to form an intimate ion pair, which is followed by a swift nucleophilic attack of the phenolate oxygen on keteniminium, fulfilling the overall hydrofunctionalization event. This protocol is operationally simple and easily scalable, tolerates a wide variety of functional groups, and shows good compatibility with the requirements of modern green chemistry.
View Article and Find Full Text PDFStereodivergent synthesis of 1,4-dicarbonyls by traceless charge-accelerated sulfonium rearrangement.
Science
August 2018
Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090 Vienna, Austria
The chemistry of the carbonyl group is essential to modern organic synthesis. The preparation of substituted, enantioenriched 1,3- or 1,5-dicarbonyls is well developed, as their disconnection naturally follows from the intrinsic polarity of the carbonyl group. By contrast, a general enantioselective access to quaternary stereocenters in acyclic 1,4-dicarbonyl systems remains an unresolved problem, despite the tremendous importance of 2,3-substituted 1,4-dicarbonyl motifs in natural products and drug scaffolds.
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