Synthesis, spectral characterization and biological activities of o,o'-dihydroxyazo compounds containing gallic acid: Molecular docking and dynamics simulation and MM-PBSA studies

IF 3.2 4区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY
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引用次数: 0

Abstract

In the investigation, diazonium derivatives of 2-aminophenol, 2-amino-4-methylphenol, 2-amino-4-chlorophenol, and 2-amino-5-nitrophenol reacted with gallic acid to produce four distinct o,o'-dihydroxyazo compounds. Description of the o,o'-dihydroxyazo compounds that were produced identified the substituent spectrum data using UV–Vis, FT-IR, NMR spectroscopy and MS spectrometry methods. The UV–Vis behaviors of compounds in ethanol and DMSO were noted at various pH values. The antioxidant, antimicrobial, and urease inhibitory activities of the compounds were determined spectrophotometrically and compared to standard compounds. The DPPH˙ scavenging and metal chelating activities of compound 4b were 2.17 ± 0.04 and 11.62 ± 0.64 μg/mL, respectively. Compounds exhibited an effective antibacterial activity against B. cereus. The urease inhibition capacity of compound 4c (IC50: 4.79 ± 0.01 μg/mL) was more effective than thiourea (IC50: 20.04 ± 0.16 μg/mL). Moreover, molecular docking calculations were used to assess the urease inhibition potentials, inhibition kinetics, and interactions of the synthesized compounds with antimicrobial enzymes and urease. The compounds had substantial impacts on density functional theory (DFT), molecular electrostatic potential (MEP), inhibition kinetics, enzyme inhibition, and PASS prediction tests. For this reason, molecular dynamics simulation and MM-PBSA energy calculation were performed to assess the compounds' stability during urease binding.
As a result, the effective pharmacological properties of the newly synthesized o,o'-dihydroxyazo compounds were revealed by different in vitro bioactivity tests and in silico calculations.

Abstract Image

含有没食子酸的 o,o'-二羟基偶氮化合物的合成、光谱表征和生物活性:分子对接和动力学模拟以及 MM-PBSA 研究
在这项研究中,2-氨基苯酚、2-氨基-4-甲基苯酚、2-氨基-4-氯苯酚和 2-氨基-5-硝基苯酚的重氮衍生物与没食子酸反应生成了四种不同的 o,o'-二羟基偶氮化合物。在描述所生成的 o,o'-二羟基偶氮化合物时,使用了紫外可见光谱、傅立叶变换红外光谱、核磁共振光谱和质谱分析方法确定了取代基光谱数据。在不同的 pH 值下,化合物在乙醇和二甲基亚砜中的紫外可见光行为受到关注。用分光光度法测定了化合物的抗氧化、抗菌和抑制脲酶活性,并与标准化合物进行了比较。化合物 4b 的 DPPH˙清除活性和金属螯合活性分别为 2.17 ± 0.04 和 11.62 ± 0.64 μg/mL。化合物对蜡样芽孢杆菌具有有效的抗菌活性。化合物 4c 的脲酶抑制能力(IC50:4.79 ± 0.01 μg/mL)比硫脲(IC50:20.04 ± 0.16 μg/mL)更有效。此外,还利用分子对接计算评估了合成化合物的脲酶抑制潜力、抑制动力学以及与抗菌酶和脲酶的相互作用。这些化合物对密度泛函理论(DFT)、分子静电位(MEP)、抑制动力学、酶抑制和 PASS 预测测试产生了重大影响。因此,通过不同的体外生物活性测试和硅学计算,揭示了新合成的 o,o'-二羟基偶氮化合物的有效药理特性。
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来源期刊
CiteScore
3.50
自引率
7.70%
发文量
492
审稿时长
3-8 weeks
期刊介绍: The Journal of the Indian Chemical Society publishes original, fundamental, theorical, experimental research work of highest quality in all areas of chemistry, biochemistry, medicinal chemistry, electrochemistry, agrochemistry, chemical engineering and technology, food chemistry, environmental chemistry, etc.
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