10.1016/j.jfluchem.2020.109516
The research focuses on the development of a general methodology for the trifluoromethylation of 1-aryl-4-iodo-1,2,3-triazoles using methyl-2,2-difluoro-2-(fluorosulfonyl) acetate (MDFA) and copper (I) iodide, promoted by tetrabutylammonium iodide (TBAI). The study explores the synthesis of 1-aryl-4-trifluoromethyl-1,2,3-triazoles, which are important due to the unique properties of the 1,2,3-triazole ring and the significance of the trifluoromethyl group in pharmaceuticals and agrochemicals. The experiments involved the optimization of reaction conditions, including the evaluation of different solvents, copper sources, and additives, with a particular emphasis on the role of TBAI in enhancing conversion rates. The analyses used to monitor the progress and outcomes of the reactions included liquid chromatography-mass spectrometry (LCMS), high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR) spectroscopy, and high-resolution mass spectrometry (HRMS). These techniques were crucial for characterizing the intermediates and final products, as well as for optimizing the reaction conditions to achieve the desired trifluoromethylated heterocycles with broad functional group tolerance and on a multi-gram scale.
10.1007/s11167-005-0391-z
The research focuses on the synthesis and antioxidant activity of N,N-dialkyl-ω-[4-hydroxy(methoxy)aryl]alkylamines and their N-oxides. The purpose of this study was to prepare aminoalkylphenols with varying structures by reacting ω-[4-hydroxy(methoxy)aryl]haloalkanes with dialkylamines and to compare their inhibiting activities in the thermal autooxidation of lard, a model reaction. The researchers also synthesized the corresponding N-oxides by oxidizing the aminoalkylphenols with hydrogen peroxide and cumene hydroperoxide. The conclusions drawn from the study indicate that these synthesized aminoalkylphenols, due to their bifunctional antioxidative mechanism and the occurrence of intramolecular synergism, exhibit higher inhibiting activity compared to commercial antioxidants and thus show potential as inhibitors for preventing oxidation in fat-containing products. The study also found that the inhibiting activity of these compounds increases with the distance between the nitrogen atom and the aromatic core, decreases with the length of N-alkyl substituents, and increases with the extent of steric shielding of the phenolic OH group.
10.1248/cpb.43.1724
The researchers synthesized numerous 2(1H)-quinolinone derivatives and identified 3,4-dihydro-6-[3-(1-o-tolylimidazol-2-yl)sulfinylpropoxy]-2(1H)-quinolinone (Sk) as a potent inhibitor of 12-HETE release, surpassing esculetin in potency. Further investigation into the enantiomers of Sk revealed that (S)-(+)-Sk exhibited the best pharmacological profile and was selected for further development. The study discusses structure-activity relationships and concludes that (S)-(+)-Sk has the optimal structure for inhibitory activity. Key chemicals used in the synthesis process include cilostazol, esculetin, various 2(1H)-quinolinone derivatives, and reagents such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), m-chloroperbenzoic acid (mCPBA), and cumene hydroperoxide.
10.1016/j.tet.2012.09.020
The study investigates the role of steric and electronic effects on the antioxidant activity of tertiary amine-based diaryl diselenides, which mimic the function of glutathione peroxidase (GPx). The researchers synthesized various diselenides with methoxy substituents at different positions and evaluated their GPx-like activities using hydrogen peroxide, tert-butyl hydroperoxide, and cumene hydroperoxide as substrates, with thiophenol (PhSH) and glutathione (GSH) as co-substrates. The findings indicate that the position of the methoxy substituent significantly influences the catalytic activity. Specifically, the 6-methoxy substituent provides steric protection, preventing undesired thiol exchange reactions and the formation of seleninic and selenonic acids, thereby enhancing GPx-like activity. In contrast, the 4-methoxy substituent enhances activity when GSH is used as the co-substrate, likely due to its electronic effects. The study provides insights into the design of more effective GPx mimics by understanding the impact of substituent positions on the catalytic cycle and reactivity of these compounds.
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