Biological and computational studies of novel scaffolds of gallic acid: insight from density functional theory and molecular docking studies

Analytical Chemistry Letters Pub Date : 2023-09-03 DOI:10.1080/22297928.2023.2283451

Shariqah Hijazi, Nayeem Ahmed, H. Louis, Imojara Anna, W. A. Shah

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Abstract

Abstract In this study, we carried out the isolation of gallic acid from Hippophae rhamnoides plant followed by synthetic modification by using Dicyclohexyl carbodimide (DCC) as a coupling reagent. The synthetic modification involves the amidation of Gallic acid by a one-step protocol, converting gallic acid to its corresponding amide derivatives. The reactions involve a simple one-pot procedure with the formation of a chain of scaffolds of various beneficial amides in good to outstanding yields. The synthesized amides were characterized by several spectroscopic techniques like FTIR, HNMR, and Mass spectrometry. The synthetic derivatives were theoretically studied by Density Functional Theory (DFT) and their biological structural feasibility was studied by docking studies. Moreover, the antibacterial activities of the derivatives were also evaluated, and it is worthwhile to mention that all compounds have shown good antibacterial activity with the highest inhibition zone of 21 mm (A2) against strains of gram-positive and gram-negative bacteria with MIC value of 40 mg/mL. GRAPHICAL ABSTRACT

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没食子酸新型支架的生物学和计算研究：密度泛函理论和分子对接研究的启示

摘要在这项研究中，我们从鼠李糖植物中分离出没食子酸，然后用二环己基碳二亚胺（DCC）作为偶联试剂进行合成修饰。合成改性包括一步法酰胺化没食子酸，将没食子酸转化为相应的酰胺衍生物。反应采用简单的一步法进行，可形成一连串各种有益酰胺的支架，产率从良好到卓越。傅立叶变换红外光谱、氢核磁共振和质谱等光谱技术对合成的酰胺进行了表征。通过密度泛函理论（DFT）对合成的衍生物进行了理论研究，并通过对接研究对其生物结构的可行性进行了研究。此外，还对这些衍生物的抗菌活性进行了评估，值得一提的是，所有化合物都表现出了良好的抗菌活性，对革兰氏阳性菌和革兰氏阴性菌菌株的最高抑菌区为 21 mm (A2)，MIC 值为 40 mg/mL。图表摘要

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来源期刊

Analytical Chemistry Letters

CiteScore

2.30

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