A Selectfluor-mediated approach for the synthesis of β-acyl allyl sulfones/β-acyl allyl benzotriazoles with excellent atom economy from readily available acetophenones/aryl acetylenes, aryl sulfinates/benzotriazoles, and dimethyl sulfoxide (DMSO) is described. In this protocol, DMSO acts as a dual-carbon synthon, resulting in a transition-metal-free construction of two C-C and one C-S or two C-C and one C-N bonds in one pot. This approach is extended to generate chemically diverse compounds. Additionally, β-acyl allyl sulfones/β-acyl allyl benzotriazoles were prepared from acetylenes instead of acetophenones.
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http://dx.doi.org/10.1021/acs.joc.1c02348 | DOI Listing |
J Am Chem Soc
January 2025
Institute of Chemical Biology, Shenzhen Bay Laboratory, Shenzhen 518132, China.
The absolute and relative configurations of bioactive chiral molecules are typically relevant to their biological properties. It is thus highly important and desirable to construct all possible stereoisomers of a lead candidate or a given bioactive natural compound. Synergistic dual catalysis has been recognized as a reliable synthetic strategy for a variety of predictable stereodivergent transformations.
View Article and Find Full Text PDFArch Biochem Biophys
January 2025
Microbial Biotechnology, Faculty of Biology and Biotechnology, Ruhr University Bochum, Universitaetsstrasse 150, 44780 Bochum, Germany.
4-Phenol oxidases are proposed to be involved in the utilization of lignin-derived aromatic compounds. While enzymes with selectivity towards 4-hydroxyphenyl and guaiacyl motifs are well described, we identified the first syringyl-specific oxidase from Streptomyces cavernae (Sc4ASO) only very recently. Here, in-depth studies were conducted to unravel the molecular origins of the outstanding selectivity of Sc4ASO.
View Article and Find Full Text PDFJ Agric Food Chem
January 2025
Institute of Quality Standard and Testing Technology for Agro-Products, Shandong Academy of Agricultural Sciences, Jinan 250100, Shandong, China.
γ-l-Glutamyl-S-allyl-l-cysteine (GSAC) is renowned for its flavor-modifying effects and beneficial biological activities. However, the level of GSAC decreases significantly during the processing of black garlic, and the pathways and degradation products resulting from this decline remain unclear. To investigate the potential transformation mechanisms of GSAC in black garlic, simulation systems for thermal decomposition, Maillard reactions, and enzymatic hydrolysis were established.
View Article and Find Full Text PDFPharmaceuticals (Basel)
January 2025
School of Pharmacy and Pharmaceutical Sciences, Panoz Institute, Trinity College Dublin, D02 PN40 Dublin, Ireland.
The synthesis of ()-1-(1,3-diphenylallyl)-1-1,2,4-triazoles and related compounds as anti-mitotic agents with activity in breast cancer was investigated. These compounds were designed as hybrids of the microtubule-targeting chalcones, indanones, and the aromatase inhibitor letrozole. : A panel of 29 compounds was synthesized and examined by a preliminary screening in estrogen receptor (ER) and progesterone receptor (PR)-positive MCF-7 breast cancer cells together with cell cycle analysis and tubulin polymerization inhibition.
View Article and Find Full Text PDFMolecules
January 2025
Université de Reims Champagne-Ardenne, CNRS, ICMR, 51097 Reims, France.
A straightforward synthetic route towards DAB-1 scaffolded dimeric iminosugars is described here, starting from readily available bis-glycosylamines. The method allows the integration of a variety of linkages (aryl, alkyl, polyethyleneglycol chains) between both iminosugars through the choice of the bis-amine used in the first step. Moreover, an additional substituent (allyl, ethynyl) may be inserted into the structure via nucleophilic addition of an organometallic reagent to the starting bis-glycosylamine.
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