Heterocyclic electrophiles as small covalent fragments showed promising inhibitory activity on the antibacterial target MurA (UDP-N-acetylglucosamine 1-carboxyvinyltransferase, EC:2.5.1.7). Here, we report the second generation of heterocyclic electrophiles: the quaternized analogue of the heterocyclic covalent fragment library with improved reactivity and MurA inhibitory potency. Quantum chemical reaction barrier calculations, GSH (-glutathione) reactivity assay, and thrombin counter screen were also used to demonstrate and explain the improved reactivity and selectivity of the -methylated heterocycles and to compare the two generations of heterocyclic electrophiles.
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http://dx.doi.org/10.3390/ph15121484 | DOI Listing |
Chem Rec
January 2025
Department of Chemistry, Jadavpur University, 188, Raja Subodh Chandra Mallick Rd, Jadavpur, Kolkata, West Bengal, 700032, India.
Selectfluor, [1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)], is a highly valuable reagent in contemporary chemistry, serving not only as an electrophilic fluorinating agent but also as an effective catalyst in the synthesis of various pharmaceutically relevant heterocycles.
View Article and Find Full Text PDFOrg Lett
January 2025
Department of Chemistry, University of Hawai'i at Ma̅noa, Honolulu, Hawaii 96822, United States.
We present a photocatalytic method for alkylamination of alkenes, enabling efficient C-C and C-N bond formation to construct aza-heterocycles valuable in drug discovery. Using a radical-polar crossover pathway, electron-deficient alkenes are reduced to electrophilic radicals, which react with electron-rich alkenes to form nucleophilic radicals. Oxidation of these intermediates yields carbocations, which are trapped by aza-heteroarenes to afford alkylaminated products.
View Article and Find Full Text PDFFood Res Int
January 2025
College of Food Science and Nutritional Engineering, National Engineering Research Centre for Fruits and Vegetables Processing, Key Laboratory of Storage and Processing of Fruits and Vegetables, Ministry of Agriculture, Engineering Research Centre for Fruits and Vegetables Processing, Ministry of Education, China Agricultural University, Beijing 100083, China. Electronic address:
Reactive carbonyl species (RCS) are a class of compounds with one or more C = O structures with highly reactive electrophilic properties. This comprehensive review delves into the multifaceted role of RCS in thermally processed foods, where they serve as both crucial intermediates in the development of food color and flavor, as well as precursors of potentially harmful compounds. By exploring the carbonyl pool concept, the impact of RCS equilibrium on the formation and reduction of hazardous substances such as acrylamide, hydroxymethylfurfural, advanced glycation end-products, and heterocyclic amines was elucidated.
View Article and Find Full Text PDFDalton Trans
January 2025
Institut für Anorganische Chemie, University of Stuttgart, Pfaffenwaldring 55, 70550 Stuttgart, Germany.
Med Chem
January 2025
Graduate School of NanoBio Sciences, Yokohama City University, 22-2, Seto, Kanazawa-Ku, Yokohama 236-0027, Japan.
Aim: There is an urgent need for new antimicrobial compounds with alternative modes of action for the treatment of drug-resistant bacterial and fungal pathogens.
Background: Carbohydrates and their derivatives are essential for biochemical and medicinal research because of their efficacy in the synthesis of biologically active drugs.
Objective: In the present study, a series of methyl α-D-mannopyranoside (MMP) derivatives (2-6) were prepared via direct acylation, and their biological properties were characterized.
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