Synthesis and Antibacterial Activity of New Amide Derivatives of Pyrimidinediones

IF 0.2 4区 化学 Q4 CHEMISTRY, ORGANIC Indian Journal of Heterocyclic Chemistry Pub Date : 2023-09-30 DOI:10.59467/ijhc.2023.33.311
Mary Nygi, L. Aruna Priya, Shalini Devi, B. Prashanthi, S. Kalyani
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Abstract

A series of ten new pyrimidinedione derivatives (4a-j) was synthesized from a common scaffold, 1-(((benzyloxy) carbonyl)methyl)-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carboxylic acid (2). The compound (2) was subjected to acid– amine coupling with different amines 3(a-j). The coupling reaction was performed using HATU as a coupling reagent at room temperature for 3h using the base N-methylmorpholine and solvent DMF. The desired derivatives were obtained with good yields. The synthesized compound’s purity was determined by HPLC analytical techniques. The structures of the pyrimidinediones were analyzed by Fourier-transform infrared spectroscopy, proton nuclear magnetic resonance (1H NMR), 13C NMR, liquid chromatography–mass spectrometry, and Human Resource Management System data. All ten amide derivatives were tested for antibacterial efficacy using Staphylococcus aureus (Gram-positive strain bacteria) and Pseudomonas putida (Gram-negative strain bacteria). Compounds 4g as well as 4h showed significant antibacterial effectiveness, with good minimum inhibition concentration values. A molecular docking study was also performed with the protein 3FQO selected from the Protein Data Bank. The amide compounds 4g and 4h displayed good docking scores. The results of the in silico study complemented the antibacterial effectiveness of the two analogs 4g and 4h. The presence of electron donating groups in these target molecules may be attributed to their high efficacy.
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新型嘧啶二酮酰胺类衍生物的合成及抗菌活性研究
以1-((苄氧基)羰基)甲基为骨架,合成了一系列10个新的嘧啶二酮衍生物(4a-j)。化合物(2)与不同的胺3(A -j)进行了酸胺偶联。以HATU为偶联剂,以n -甲基啉为基料,溶剂DMF为溶剂,在室温下进行3h的偶联反应。得到了所需的衍生物,收率高。采用高效液相色谱法测定合成化合物的纯度。采用傅里叶变换红外光谱、质子核磁共振(1H NMR)、13C NMR、液相色谱-质谱联用以及人力资源管理系统(Human Resource Management System)数据分析了嘧啶二酮类化合物的结构。采用金黄色葡萄球菌(革兰氏阳性菌)和恶臭假单胞菌(革兰氏阴性菌)对10种酰胺类衍生物进行抑菌试验。化合物第4g和第4h抗菌效果显著,具有较好的最小抑菌浓度。从蛋白质数据库中选择蛋白3FQO进行分子对接研究。酰胺类化合物4g和4h的对接分数较高。硅晶研究的结果补充了两种类似物4g和4h的抗菌效果。在这些靶分子中存在给电子基团可能是由于它们的高功效。
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来源期刊
CiteScore
0.40
自引率
33.30%
发文量
0
审稿时长
6-12 weeks
期刊介绍: Indian Journal of Heterocyclic Chemistry is exclusively devoted to research in the area of heterocyclic chemistry. The journal publishes invited review articles and original research papers pertaining to structure and synthesis, mechanism of reactions, spectral studies, biologically active compounds, bio-chemical studies, physicochemical work, phytochemistry etc.
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