茚三酮单锅多组分绿色合成法制备的吡咯并[1,2-a]咪唑衍生物的生物活性研究

IF 1.6 4区 医学 Q4 BIOCHEMICAL RESEARCH METHODS
Khatereh Khandan Barani, Samira Khandan, Hannaneh Sadat Shirangi, Navisa Tabarsaei
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引用次数: 0

摘要

目的与目标:本研究旨在通过化学合成法创造一种具有特殊功效的吡咯咪唑新变体。合成是在水溶液中利用茚三酮、二胺和活化乙炔化合物进行三组分反应完成的,因此产量很高。最近合成的吡咯并咪唑衍生物的抗氧化特性归因于 NH 和 OH 基团的存在,并使用两种技术对其进行了评估。材料和方法:研究小组使用了化学和物理性质一致的高质量起始化学品、溶剂和试剂。在 KBr 介质中使用岛津 IR-460 光谱仪获得合成纳米催化剂的傅立叶变换红外光谱。此外,我们还使用布鲁克 DRX-400 AVANCE 光谱仪获取了合成化合物的 1H-NMR 和 13C-NMR 光谱。本次研究中使用的光谱仪频率为 400 MHz。合成化合物的光谱所用溶剂为 CDCl3,内标为 TMS。使用 Finnigan MAT 8430 光谱仪获得了电离电位为 70 eV 的化合物质谱。使用 Heraeus CHN-O-Rapid 分析仪对生成的化合物进行元素分析:这项工作研究了茚1、二胺2和缺电子乙炔化合物3在常温水基溶液中以环保方式生产吡咯咪唑衍生物4的三组分反应。结果表明,这些分子具有与传统抗氧化剂类似的显著功效。结果还表明,合成的吡咯咪唑具有抑菌特性:综上所述,本研究旨在探讨茚、二胺和缺电子乙炔化合物在常温下溶于水时的环境友好特性。研究结果是成功生产出新的吡咯咪唑衍生物,成功率很高。本研究利用两种技术对合成的吡咯咪唑 4a-4d 的抗氧化性进行了更深入的分析:DPPH 自由基清除试验和 FRAP 试验。结果表明,这些分子具有与传统抗氧化剂类似的显著功效。此外,我们还利用革兰氏阳性菌和革兰氏阴性菌,通过盘扩散技术展示了合成的吡咯咪唑的抗菌效果。结果表明,合成的吡咯并咪唑具有抑菌特性。这些反应具有高效利用原子、生成大量产物和反应直接等优点。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Investigation of the Biological Activity of Pyrrolo[1,2-a]imidazole Derivatives Produced by a Green One-Pot Multicomponent Synthesis of Ninhydrins.

Aims & Objective: This study entailed the creation of a new variation of pyrroloimidazoles with exceptional efficacy through chemical synthesis. The synthesis was accomplished by tricomponent reactions utilizing ninhydrins, diamines, and activated acetylenic compounds in an aqueous setting, leading to significant yields. The antioxidant properties of recently synthesized Pyrroloimidazoles derivatives have been ascribed to the existence of NH and OH groups, which were evaluated using two techniques. The antimicrobial effectiveness of recently developed pyrroloimidazoles was evaluated using a disk diffusion technique against both Gram-negative and Gram-positive bacteria.

Materials and methods: The study team utilized high-quality starting chemicals, solvents, and reagents with consistent chemical and physical properties. The Shimadzu IR-460 spectrometer was used in a KBr medium to get the Ft-IR spectra of the synthesized nanocatalyst. Furthermore, we employed a Bruker DRX-400 AVANCE spectrometer to acquire 1H-NMR and 13C-NMR spectra of the synthesized compounds. The spectrometer utilized in this investigation functions at a frequency of 400 MHz. The solvent employed for the spectra of produced compounds was CDCl3, with TMS serving as the internal standard. The mass spectra of the produced compounds, which have an ionization potential of 70 eV, were obtained using the Finnigan MAT 8430 spectrometer. Elements of produced compounds were subjected to elemental analysis using the Heraeus CHN-O-Rapid analyzer.

Results: This work investigated the three-component reaction involving ninhydrins 1, diamines 2, and electron-deficient acetylenic compounds 3 for the eco-friendly production of pyrroloimidazoles derivatives 4 in water-based solutions at normal temperature. The results indicated that these molecules displayed noteworthy efficacy, similar to that of conventional antioxidants. Also, the results indicated that the synthesized pyrroloimidazoles have bacteriostatic properties.

Conclusion: In summary, this study aimed to examine the environmentally friendly characteristics of ninhydrins, diamines, and electron-deficient acetylenic compounds when dissolved in water at normal room temperature. The research resulted in the successful production of new pyrroloimidazole derivatives with a high rate of success. This study conducted a more in-depth analysis of the antioxidant properties of the synthesized pyrroloimidazoles 4a-4d by the utilization of two techniques: DPPH radical scavenging and FRAP assays. The results indicated that these molecules displayed noteworthy efficacy, similar to that of conventional antioxidants. Furthermore, we utilized both Gram-positive and Gram-negative bacteria to showcase the antibacterial effectiveness of the synthesized pyrroloimidazoles by the disk diffusion technique. The results indicated that the synthesized pyrroloimidazoles have bacteriostatic properties. These reactions provide benefits, such as efficient utilization of atoms, generation of large quantities of products, and straightforwardness of the reaction.

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来源期刊
CiteScore
3.10
自引率
5.60%
发文量
327
审稿时长
7.5 months
期刊介绍: Combinatorial Chemistry & High Throughput Screening (CCHTS) publishes full length original research articles and reviews/mini-reviews dealing with various topics related to chemical biology (High Throughput Screening, Combinatorial Chemistry, Chemoinformatics, Laboratory Automation and Compound management) in advancing drug discovery research. Original research articles and reviews in the following areas are of special interest to the readers of this journal: Target identification and validation Assay design, development, miniaturization and comparison High throughput/high content/in silico screening and associated technologies Label-free detection technologies and applications Stem cell technologies Biomarkers ADMET/PK/PD methodologies and screening Probe discovery and development, hit to lead optimization Combinatorial chemistry (e.g. small molecules, peptide, nucleic acid or phage display libraries) Chemical library design and chemical diversity Chemo/bio-informatics, data mining Compound management Pharmacognosy Natural Products Research (Chemistry, Biology and Pharmacology of Natural Products) Natural Product Analytical Studies Bipharmaceutical studies of Natural products Drug repurposing Data management and statistical analysis Laboratory automation, robotics, microfluidics, signal detection technologies Current & Future Institutional Research Profile Technology transfer, legal and licensing issues Patents.
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