Catalyst free regiospecific amination, structural elucidation, and potential utilization of pyran-2,4‑dione derivatives as novel antimicrobial agents

IF 4 2区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Molecular Structure Pub Date : 2025-02-27 DOI:10.1016/j.molstruc.2025.141893

Ahmed A.M. Sarhan , Matti Haukka , Saied M. Soliman , Assem Barakat , Ahmed T.A. Boraei

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Abstract

Catalyst-free regiospecific amination at the C-4 position of 3-benzoyl-4‑chloro-6-phenyl-2H-pyran-2-one precursor 3 was explored using various aminating agents such as ammonium acetate, primary aliphatic and aromatic amines in methanol. Structural investigation mainly based on NMR and X-ray single crystal analyses are presented. In addition, topology analysis of molecular packing was performed using Hirshfeld calculations. The antimicrobial activity of the newly synthesized aminated analogues compared to their β-enamino-pyran-2,4‑dione isomers was assessed against S. aureus and C. albicans. In general, the β-enamino-pyran-2,4-diones displayed better antimicrobial activity against S. aureus and C. albicans compared to their C4-aminated isomers and conventional medications (Neomycin, Streptomycin, and Amoxicillin + Co-amoxiclav).

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来源期刊

Journal of Molecular Structure 化学-物理化学

CiteScore

7.10

自引率

15.80%

发文量

2384

审稿时长

45 days

期刊介绍： The Journal of Molecular Structure is dedicated to the publication of full-length articles and review papers, providing important new structural information on all types of chemical species including: • Stable and unstable molecules in all types of environments (vapour, molecular beam, liquid, solution, liquid crystal, solid state, matrix-isolated, surface-absorbed etc.) • Chemical intermediates • Molecules in excited states • Biological molecules • Polymers. The methods used may include any combination of spectroscopic and non-spectroscopic techniques, for example: • Infrared spectroscopy (mid, far, near) • Raman spectroscopy and non-linear Raman methods (CARS, etc.) • Electronic absorption spectroscopy • Optical rotatory dispersion and circular dichroism • Fluorescence and phosphorescence techniques • Electron spectroscopies (PES, XPS), EXAFS, etc. • Microwave spectroscopy • Electron diffraction • NMR and ESR spectroscopies • Mössbauer spectroscopy • X-ray crystallography • Charge Density Analyses • Computational Studies (supplementing experimental methods) We encourage publications combining theoretical and experimental approaches. The structural insights gained by the studies should be correlated with the properties, activity and/ or reactivity of the molecule under investigation and the relevance of this molecule and its implications should be discussed.