Synthesis, X-ray, DFT and antibacterial activity of a novel 1-indanone derivative

IF 4.7 2区化学 Q2 CHEMISTRY, PHYSICAL Journal of Molecular Structure Pub Date : 2025-09-05 Epub Date: 2025-04-17 DOI:10.1016/j.molstruc.2025.142422

Mei Zuo , Yang Chen , Hongyi Zhao , Ting Wu , Shuzhong He , Jian Huang

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Abstract

1-Indanone is a prominent scaffold recognized for its wide range of biological activities. Numerous studies have demonstrated that 1-indanone derivatives are crucial for Alzheimer's disease, antidiarrheal, anti-proliferative, antibacterial, anti-inflammatory, anticancer agents, etc. In recent years, it has been found that this type of compound also has significant anti-plant disease activity. Novel 1-indanone derivatives were designed and synthesized based on their extensive biological activities. The compounds were characterized using ¹H NMR, ¹³C NMR, and high-resolution mass spectrometry (HRMS). Compound 11 (CCDC number: 2391,391) was crystallized, and its structure was determined through X-ray analysis. Additionally, density functional theory (DFT) calculations for compound 11 were conducted at the B3LYP/6–311 level. Ultimately, systematic biological assays indicated that the intermediate 6 exhibited significant inhibitory activity in vitro against the four tested plant pathogenic bacteria.

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新型 1-茚酮衍生物的合成、X 射线、DFT 和抗菌活性

1-吲哚酮是一种重要的支架，具有广泛的生物活性。大量研究表明，1-吲哚酮衍生物在阿尔茨海默病、止泻、抗增殖、抗菌、抗炎、抗癌等方面发挥着至关重要的作用。近年来，人们发现这类化合物还具有显著的抗植物病害活性。基于其广泛的生物活性，设计并合成了新的1-吲哚酮衍生物。采用1H NMR、13C NMR和高分辨率质谱（HRMS）对化合物进行了表征。化合物11 （CCDC编号：2391,391）结晶，并通过x射线分析确定其结构。此外，在B3LYP/ 6-311水平上对化合物11进行了密度泛函理论（DFT）计算。最终，系统生物学实验表明，中间体6对四种植物病原菌具有显著的体外抑制活性。

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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.