Mary Nygi, L. Aruna Priya, Shalini Devi, B. Prashanthi, S. Kalyani
{"title":"Synthesis and Antibacterial Activity of New Amide Derivatives of Pyrimidinediones","authors":"Mary Nygi, L. Aruna Priya, Shalini Devi, B. Prashanthi, S. Kalyani","doi":"10.59467/ijhc.2023.33.311","DOIUrl":null,"url":null,"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.","PeriodicalId":54993,"journal":{"name":"Indian Journal of Heterocyclic Chemistry","volume":"59 1","pages":"0"},"PeriodicalIF":0.2000,"publicationDate":"2023-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Indian Journal of Heterocyclic Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.59467/ijhc.2023.33.311","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
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.
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.