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

IF 4.7 2区化学 Q2 CHEMISTRY, PHYSICAL Journal of Molecular Structure Pub Date : 2025-07-05 Epub 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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吡喃-2,4 -二酮衍生物作为新型抗菌剂的无催化剂区域特异性胺化、结构解析和潜在应用

采用乙酸铵、伯脂肪胺和芳香胺等不同的胺化剂，在甲醇中研究了3-苯甲酰-4 -氯-6-苯基- 2h -吡喃-2- 1前体3在C-4位置的无催化剂区域特异性胺化。主要介绍了基于核磁共振和x射线单晶分析的结构研究。此外，利用Hirshfeld计算对分子填料进行了拓扑分析。新合成的胺化类似物与β-氨基-吡喃-2,4 -二酮异构体比较，对金黄色葡萄球菌和白色念珠菌的抑菌活性进行了评价。总的来说，β-氨基吡喃-2,4-二酮对金黄色葡萄球菌和白色念珠菌的抗菌活性优于它们的c4胺化异构体和常规药物（新霉素、链霉素和阿莫西林+ co -阿莫西林）。

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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.