2-methyl-4-oxo-1,2,3,4-四氢喹唑啉-2-羧酸的微波辅助合成、结构表征、DFT研究、抗菌和抗氧化活性,Journal of Molecular Structure

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2-methyl-4-oxo-1,2,3,4-四氢喹唑啉-2-羧酸的微波辅助合成、结构表征、DFT研究、抗菌和抗氧化活性
Journal of Molecular Structure ( IF 4.0 ) Pub Date : 2018-03-01 , DOI: 10.1016/j.molstruc.2017.11.018
Craig A. Obafemi , Olatomide A. Fadare , Jerry P. Jasinski , Sean P. Millikan , Efere M. Obuotor , Ezekiel O. Iwalewa , Samson O. Famuyiwa , Kayode Sanusi , Yusuf Yilmaz , Ümit Ceylan

摘要本研究合成了一种新的四氢喹唑啉-2-羧酸，C 10 H 10 N 2 O 3 , 1′ ，并通过元素分析、红外、 1 H NMR、 13 C NMR 数据和高分辨率表征了其结构。质谱。光谱结果与所提出的结构一致。该化合物的单晶X射线结构分析表明，该晶体结构采用单斜空间群P 2 1 / c ，分子的堆积由CO … …HO、NH … ….OCO分子间氢键稳定。使用密度泛函（DFT）和时间相关密度泛函（TD-DFT）理论方法计算了化合物的理论几何参数，并用于预测化合物的热力学单电子氧化还原电位和电子吸收性能. 理论表征与实验测量相匹配，显示出良好的相关性。计算出的 HOMO-LUMO 间隙（4.79 eV）表明化合物 1' 可能是一种潜在的抗氧化剂。使用 TAC、FRAP、NO 和 ABTS 模型筛选合成的化合物对选定细菌菌株的体外抗微生物活性和抗氧化活性。1'的体外抗氧化活性表现出中等活性，但清除活性比标准抗坏血酸和trolox弱。受试化合物抗菌活性结果表明，其对炭疽芽孢杆菌、蜡样芽孢杆菌、多粘芽孢杆菌、枯草芽孢杆菌和金黄色葡萄球菌的活性高于链霉素和四环素两种标准药物，

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Microwave-assisted synthesis, structural characterization, DFT studies, antibacterial and antioxidant activity of 2-methyl-4-oxo-1,2,3,4-tetrahydroquinazoline-2-carboxylic acid

Abstract In the present study a new tetrahydroquinazoline-2-carboxylic, C 10 H 10 N 2 O 3 , 1′ , was synthesized and its structure was characterized by elemental analysis, IR, 1 H NMR, 13 C NMR data and high-resolution mass spectrometry. The spectral results are in line with the proposed structure. Single crystal X-ray structural analysis of the compound showed that the crystal structure adopts a monoclinic space group P 2 1 / c , with the packing of the molecule stabilized by C O … …H O, N H … ….O C O intermolecular hydrogen bonding. The theoretical geometrical parameters of the compound have been calculated using density functional (DFT) and time-dependent density functional (TD-DFT) theory methods and have been used to predict the thermodynamic one-electron redox potential and the electronic absorption property of the compound. The theoretical characterization matched the experimental measurements, showing a good correlation. The calculated HOMO-LUMO gap (4.79 eV) suggests that compound 1′ could be a potential antioxidant. The synthesized compound was screened for its in vitro antimicrobial activity against selected bacterial strains and antioxidant activity using the TAC, FRAP, NO and ABTS models. In vitro antioxidant activity of 1' showed a moderate activity, but weaker scavenging activity than the standards of ascorbic acid and trolox. Results of the antibacterial activity of the tested compound showed that it possesses a higher activity against Bacillus anthracis , Bacillus cereus , Bacillus polymyxa , Bacillus subtilis and Staphylococcus aureus than the two standard drugs, streptomycin and tetracycline, and better activity than tetracycline against Escherichia coli.

更新日期：2018-03-01

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